{"id":642,"date":"2017-10-04T21:09:23","date_gmt":"2017-10-04T21:09:23","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/?post_type=chapter&#038;p=642"},"modified":"2017-10-24T15:55:03","modified_gmt":"2017-10-24T15:55:03","slug":"functional-groups","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/chapter\/functional-groups\/","title":{"raw":"Functional Groups","rendered":"Functional Groups"},"content":{"raw":"<div class=\"elm-header\"><\/div>\r\n<div id=\"elm-main-content\" class=\"elm-content-container\">\r\n<div>\r\n<div id=\"skills\">\r\n<div class=\"textbox learning-objectives\">\r\n<h3>Objectives<\/h3>\r\nAfter completing this section, you should be able to\r\n<ol>\r\n \t<li>explain why the properties of a given organic compound are largely dependent on the functional group or groups present in the compound.<\/li>\r\n \t<li>identify the functional groups present in each of the following compound types: alkenes, alkynes, arenes, (alkyl and aryl) halides, alcohols, ethers, aldehydes, ketones, esters, carboxylic acids, (carboxylic) acid chlorides, amides, amines, nitriles, nitro compounds, sulfides and sulfoxides.<\/li>\r\n \t<li>identify the functional groups present in an organic compound, given its structure.<\/li>\r\n \t<li>Given the structure of an organic compound containing a single functional group, identify which of the compound types listed under Objective 2, above, it belongs to.<\/li>\r\n \t<li>draw the structure of a simple example of each of the compound types listed in Objective 2.<\/li>\r\n<\/ol>\r\n<\/div>\r\n<div class=\"textbox key-takeaways\">\r\n<h3>Key Terms<\/h3>\r\n<div>\r\n\r\nMake certain that you can define, and use in context, the key term below.\r\n<ul>\r\n \t<li>functional group<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>\r\n<div class=\"textbox\">\r\n<div id=\"note\">\r\n<h3 class=\"boxtitle\">Study Notes<\/h3>\r\nThe concept of functional groups is a very important one. We expect that you will need to refer back to tables at the end of Section 3.1 quite frequently at first, as it is not really feasible to learn the names and structures of all the functional groups and compound types at one sitting. Gradually they will become familiar, and eventually you will recognize them automatically.\r\n\r\n<\/div>\r\n<\/div>\r\n\r\n\r\n<\/div>\r\n<strong>Functional groups<\/strong> are atoms or small groups of atoms (two to four) that exhibit a characteristic reactivity. A particular functional group will almost always display its characteristic chemical behavior when it is present in a compound. Because of their importance in understanding organic chemistry, functional groups have characteristic names that often carry over in the naming of individual compounds incorporating specific groups\r\n\r\nAs we progress in our study of organic chemistry, it will become extremely important to be able to quickly recognize the most common functional groups, because they are the key structural elements that define how organic molecules react.\u00a0For now, we will only worry about drawing and recognizing each functional group, as depicted by Lewis and line structures.\u00a0Much of the remainder of your study of organic chemistry will be taken up with learning about how the different functional groups tend to behave in organic reactions.\r\n<div id=\"section_1\">\r\n\r\n\r\n<h3 class=\"editable\">Hydrocarbons and halides<\/h3>\r\nWe have already seen some examples of very common functional groups: ethene, for example, contains a carbon-carbon double bond.\u00a0This double bond is referred to, in the functional group terminology, as an <strong>alkene<\/strong>.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210723\/image085.png\" alt=\"image080.png\" width=\"412\" height=\"130\" \/>\r\n\r\nThe carbon-carbon triple bond in ethyne is the simplest example of an <strong>alkyne<\/strong> function group.\r\n\r\nWhat about ethane?\u00a0All we see in this molecule is carbon-hydrogen and carbon-carbon single bonds, so in a sense we can think of ethane as lacking a functional group entirely.\u00a0However,\u00a0we do have a general name for this \u2018default\u2019 carbon bonding pattern: molecules or parts of molecules containing only carbon-hydrogen and carbon-carbon single bonds are referred to as <strong>alkanes<\/strong>. If the carbon of an alkane is bonded to a halogen, the group is now referred to as a <a title=\"3.1 Functional Groups\" href=\"https:\/\/chem.libretexts.org\/LibreTexts\/Athabasca_University\/Chemistry_350%3A_Organic_Chemistry_I\/Chapter_3%3A_Organic_Compounds%3A_Alkanes_and_Their_Stereochemistry\/3.1_Functional_Groups\" rel=\"internal\"><strong>haloalkane<\/strong> <\/a>(fluoroalkane, chloroalkane, etc.).\u00a0 Chloroform, CHCl<sub>3<\/sub>, is an example of a simple haloalkane.\r\n\r\n<\/div>\r\n<div id=\"section_2\">\r\n\r\n\r\n<h3 class=\"editable\">Alcohols and Thiols<\/h3>\r\nWe have already seen the simplest possible example of an <strong>alcohol<\/strong> functional group in methanol.\u00a0 In the alcohol functional group, a carbon is single-bonded to an OH group (this OH group, by itself, is referred to as a <strong>hydroxyl<\/strong>). If the central carbon in an alcohol is bonded to only one other carbon, we call the group a primary alcohol.\u00a0 In secondary alcohols and tertiary alcohols, the central carbon is bonded to two and three carbons, respectively. Methanol, of course, is in class by itself in this respect.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210725\/image087.png\" alt=\"image082.png\" width=\"598\" height=\"102\" \/>\r\n\r\nThe sulfur analog of an alcohol is called a <strong>thiol<\/strong> (the prefix <em>thio<\/em>, derived from the Greek, refers to sulfur).\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210728\/image089.png\" alt=\"image084.png\" width=\"462\" height=\"102\" \/>\r\n\r\nIn an <strong>ether<\/strong> functional group, a central oxygen is bonded to two carbons. Below are the line and Lewis structures of diethyl ether, a common laboratory solvent and also one of the first medical anaesthesia agents.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210731\/image091.png\" alt=\"image086.png\" width=\"332\" height=\"75\" \/>\r\n\r\nIn <strong>sulfides<\/strong>, the oxygen atom of an ether has been replaced by a sulfur atom.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210733\/image093.png\" alt=\"image088.png\" width=\"228\" height=\"70\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_3\">\r\n\r\n\r\n<h3 class=\"editable\">Amines and Phosphates<\/h3>\r\nAmmonia is the simplest example of a functional group called <strong>amines<\/strong>.\u00a0 Just as there are primary, secondary, and tertiary alcohols, there are primary, secondary, and tertiary amines.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210736\/image095.png\" alt=\"image090.png\" width=\"535\" height=\"87\" \/>\r\n\r\nOne of the most important properties of amines is that they are basic, and are readily protonated to form <strong>ammonium<\/strong> cations.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210738\/image097.png\" alt=\"image092.png\" width=\"270\" height=\"103\" \/>\r\n\r\nPhosphorus is a very important element in biological organic chemistry, and is found as the central atom in the <strong>phosphate<\/strong> group. Many biological organic molecules contain phosphate, diphosphate, and triphosphate groups, which are linked to a carbon atom by the <strong>phosphate ester<\/strong> functionality.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210741\/image099.png\" alt=\"image094.png\" width=\"597\" height=\"152\" \/>\r\n\r\nBecause phosphates are so abundant in biological organic chemistry, it is convenient to depict them with the abbreviation 'P'.\u00a0Notice that this 'P' abbreviation includes the oxygen atoms and negative charges associated with the phosphate groups.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210743\/image101.png\" alt=\"image096.png\" width=\"270\" height=\"118\" \/>\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210745\/image103.png\" alt=\"image098.png\" width=\"438\" height=\"92\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_4\">\r\n\r\n\r\n<h3 class=\"editable\">Carbonyl Containing Functional Groups<\/h3>\r\n<div id=\"section_5\">\r\n\r\n\r\n<h4 class=\"editable\">Aldehydes and Ketones<\/h4>\r\nThere are a number of functional groups that contain a carbon-oxygen double bond, which is commonly referred to as a <strong>carbonyl<\/strong>.\u00a0<strong>Ketones<\/strong> and <strong>aldehydes<\/strong> are two closely related carbonyl-based functional groups that react in very similar ways.\u00a0In a ketone, the carbon atom of a carbonyl is bonded to two other carbons. In an aldehyde, the carbonyl carbon is bonded on one side to a hydrogen, and on the other side to a carbon.\u00a0The exception to this definition is formaldehyde, in which the carbonyl carbon has bonds to two hydrogens.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210748\/image105.png\" alt=\"image100.png\" width=\"400\" height=\"112\" \/>\r\n\r\nMolecules with carbon-nitrogen double bonds are called <strong>imines<\/strong>, or <strong>Schiff bases<\/strong>.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210750\/image107.png\" alt=\"image102.png\" width=\"105\" height=\"122\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_6\">\r\n\r\n\r\n<h4 class=\"editable\">Carboxylic acids and acid derivatives<\/h4>\r\nIf a carbonyl carbon is bonded on one side to a carbon (or hydrogen) and on the other side to a <strong>heteroatom<\/strong> (in organic chemistry, this term generally refers to oxygen, nitrogen, sulfur, or one of the halogens), the functional group is considered to be one of the \u2018<strong>carboxylic acid derivatives\u2019<\/strong>, a designation that describes a grouping of several functional groups.\u00a0The eponymous member of this grouping is the <strong>carboxylic acid<\/strong> functional group, in which the carbonyl is bonded to a hydroxyl (OH) group.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210752\/image109.png\" alt=\"image104.png\" width=\"242\" height=\"117\" \/>\r\n\r\nAs the name implies, carboxylic acids are acidic, meaning that they are readily deprotonated to form the conjugate base form, called a <strong>carboxylate<\/strong> (much more about carboxylic acids in the acid-base chapter!).\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210754\/image111.png\" alt=\"image106.png\" width=\"222\" height=\"97\" \/>\r\n\r\nIn <strong>amides<\/strong>, the carbonyl carbon is bonded to a nitrogen.\u00a0The nitrogen in an amide can be bonded either to hydrogens, to carbons, or to both. Another way of thinking of an amide is that it is a carbonyl bonded to an amine.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210756\/image113.png\" alt=\"image108.png\" width=\"432\" height=\"93\" \/>\r\n\r\nIn <strong>esters<\/strong>, the carbonyl carbon is bonded to an oxygen which is itself bonded to another carbon. Another way of thinking of an ester is that it is a carbonyl bonded to an alcohol.\u00a0<strong>Thioesters<\/strong> are similar to esters, except a sulfur is in place of the oxygen.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210758\/image115.png\" alt=\"image110.png\" width=\"287\" height=\"90\" \/>\r\n\r\nIn an <strong>acyl phosphate<\/strong>, the carbonyl carbon is bonded to the oxygen of a phosphate, and in an <strong>acid chloride<\/strong>, the carbonyl carbon is bonded to a chlorine.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210801\/image117.png\" alt=\"image112.png\" width=\"328\" height=\"115\" \/>\r\n\r\nFinally, in a <strong>nitrile<\/strong> group, a carbon is triple-bonded to a nitrogen.\u00a0Nitriles are also often referred to as <strong>cyano<\/strong> groups.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210804\/image119.png\" alt=\"image114.png\" width=\"93\" height=\"53\" \/>\r\n\r\nA single compound often contains several functional groups. The six-carbon sugar molecules glucose and fructose, for example, contain aldehyde and ketone groups, respectively, and both contain five alcohol groups (a compound with several alcohol groups is often referred to as a \u2018<strong>polyol\u2019<\/strong>).\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210805\/image121.png\" alt=\"image121.png\" width=\"348px\" height=\"113px\" \/>\r\n\r\nCapsaicin, the compound responsible for the heat in hot peppers, contains phenol, ether, amide, and alkene functional groups.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210807\/image123.png\" alt=\"image116.png\" width=\"400\" height=\"142\" \/>\r\n\r\nThe male sex hormone testosterone contains ketone, alkene, and secondary alcohol groups, while acetylsalicylic acid (aspirin) contains aromatic, carboxylic acid, and ester groups.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210809\/image125.png\" alt=\"image118.png\" width=\"445\" height=\"185\" \/>\r\n\r\nWhile not in any way a complete list, this section has covered most of the important functional groups that we will encounter in biological and laboratory organic chemistry. The table on the inside back cover provides a summary of all of the groups listed in this section, plus a few more that will be introduced later in the text.\r\n<div style=\"margin: auto\">\r\n<div id=\"section_7\">\r\n\r\n\r\n<div class=\"textbox exercises\">\r\n<h3>Exercises<\/h3>\r\n<div id=\"section_6\">\r\n<div style=\"margin: auto\">\r\n<div id=\"section_7\">\r\n<h3 class=\"editable\">Problems<\/h3>\r\n<\/div>\r\n<\/div>\r\n1: Identify the functional groups in the following organic compounds. State whether alcohols and amines are primary, secondary, or tertiary.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210812\/image127.png\" alt=\"image120.png\" width=\"537\" height=\"355\" \/>\r\n\r\n2: Draw one example each (there are many possible correct answers) of compounds fitting the descriptions below, using line structures.\u00a0 Be sure to designate the location of all non-zero formal charges. All atoms should have complete octets (phosphorus may exceed the octet rule).\r\n<ol start=\"1\">\r\n \t<li>a compound with molecular formula C<sub>6<\/sub>H<sub>11<\/sub>NO that includes alkene, secondary amine, and primary alcohol functional groups<\/li>\r\n \t<li>an ion with molecular formula C<sub>3<\/sub>H<sub>5<\/sub>O<sub>6<\/sub>P <sup>2-<\/sup> that\u00a0 includes aldehyde, secondary alcohol, and phosphate functional groups.<\/li>\r\n \t<li>A compound with molecular formula C<sub>6<\/sub>H<sub>9<\/sub>NO that has an amide functional group, and does <em>not<\/em> have an alkene group.<\/li>\r\n<\/ol>\r\n<\/div>\r\n<div id=\"section_8\">\r\n\r\n\r\n<h4 class=\"editable\">Solution<\/h4>\r\n1:\r\n\r\n[reveal-answer q=\"347160\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"347160\"]a) carboxylate, sulfide, aromatic, two amide groups (one of which is cyclic)\r\n\r\nb) tertiary alcohol, thioester\r\n\r\nc) carboxylate, ketone\r\n\r\nd) ether, primary amine, alkene[\/hidden-answer]\r\n\r\n<\/div>\r\n<\/div>\r\n\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_9\">\r\n\r\n\r\n<h2 class=\"editable\">Functional Group Tables<\/h2>\r\n<div id=\"section_10\">\r\n\r\n\r\n<h3 class=\"editable\">Exclusively Carbon Functional Groups<\/h3>\r\n<table style=\"width: 90%\">\r\n<thead>\r\n<tr>\r\n<th style=\"width: 20%\" scope=\"col\"><strong>Group Formula<\/strong><\/th>\r\n<th style=\"width: 20%\" scope=\"col\"><strong>Class Name<\/strong><\/th>\r\n<th style=\"width: 20%\" scope=\"col\"><strong>Specific Example<\/strong><\/th>\r\n<th style=\"width: 20%\" scope=\"col\"><strong>IUPAC Name<\/strong><\/th>\r\n<th style=\"width: 20%\" scope=\"col\"><strong>Common Name<\/strong><\/th>\r\n<\/tr>\r\n<\/thead>\r\n<tbody>\r\n<tr align=\"center\" valign=\"middle\">\r\n<td style=\"height: 198px;width: 112px\" rowspan=\"3\" valign=\"top\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210814\/funct1.gif\" alt=\"image\" \/><\/td>\r\n<td style=\"height: 50px\">Alkene<\/td>\r\n<td>H<sub>2<\/sub>C=CH<sub>2<\/sub><\/td>\r\n<td>Ethene<\/td>\r\n<td>Ethylene<\/td>\r\n<\/tr>\r\n<tr align=\"center\" valign=\"middle\">\r\n<td style=\"height: 54px\">Alkyne<\/td>\r\n<td>HC\u2261CH<\/td>\r\n<td>Ethyne<\/td>\r\n<td>Acetylene<\/td>\r\n<\/tr>\r\n<tr align=\"center\" valign=\"middle\">\r\n<td style=\"height: 94px\">Arene<\/td>\r\n<td>C<sub>6<\/sub>H<sub>6<\/sub><\/td>\r\n<td>Benzene<\/td>\r\n<td>Benzene<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<div id=\"section_11\">\r\n\r\n\r\n<h3 class=\"editable\">Functional Groups with Single Bonds to Heteroatoms<\/h3>\r\n<\/div>\r\n<table style=\"width: 90%\" border=\"0\">\r\n<thead>\r\n<tr>\r\n<th style=\"height: 17px;width: 20%\" scope=\"col\"><strong>Group Formula<\/strong><\/th>\r\n<th style=\"width: 20%\" scope=\"col\"><strong>Class Name<\/strong><\/th>\r\n<th style=\"width: 20%\" scope=\"col\"><strong>Specific Example<\/strong><\/th>\r\n<th style=\"width: 20%\" scope=\"col\"><strong>IUPAC Name<\/strong><\/th>\r\n<th style=\"width: 20%\" scope=\"col\"><strong>Common Name<\/strong><\/th>\r\n<\/tr>\r\n<\/thead>\r\n<tbody>\r\n<tr align=\"center\">\r\n<td style=\"height: 110px;width: 64px\" rowspan=\"3\" valign=\"top\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210815\/funct2a.gif\" alt=\"image\" \/><\/td>\r\n<td style=\"height: 37px\">Halide<\/td>\r\n<td>H<sub>3<\/sub>C-I<\/td>\r\n<td>Iodomethane<\/td>\r\n<td>Methyl iodide<\/td>\r\n<\/tr>\r\n<tr align=\"center\">\r\n<td style=\"height: 37px\">Alcohol<\/td>\r\n<td>CH<sub>3<\/sub>CH<sub>2<\/sub>OH<\/td>\r\n<td>Ethanol<\/td>\r\n<td>Ethyl alcohol<\/td>\r\n<\/tr>\r\n<tr align=\"center\">\r\n<td style=\"height: 36px\">Ether<\/td>\r\n<td>CH<sub>3<\/sub>CH<sub>2<\/sub>OCH<sub>2<\/sub>CH<sub>3<\/sub><\/td>\r\n<td>Diethyl ether<\/td>\r\n<td>Ether<\/td>\r\n<\/tr>\r\n<tr align=\"center\">\r\n<td style=\"height: 168px;width: 72px\" rowspan=\"4\" valign=\"top\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210815\/funct2b.gif\" alt=\"image\" \/><\/td>\r\n<td style=\"height: 36px\">Amine<\/td>\r\n<td>H<sub>3<\/sub>C-NH<sub>2<\/sub><\/td>\r\n<td>Aminomethane<\/td>\r\n<td>Methylamine<\/td>\r\n<\/tr>\r\n<tr align=\"center\">\r\n<td style=\"height: 64px\">Nitro Compound<\/td>\r\n<td>H<sub>3<\/sub>C-NO<sub>2<\/sub><\/td>\r\n<td>Nitromethane<\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<tr align=\"center\">\r\n<td style=\"height: 34px\">Thiol<\/td>\r\n<td>H<sub>3<\/sub>C-SH<\/td>\r\n<td>Methanethiol<\/td>\r\n<td>Methyl mercaptan<\/td>\r\n<\/tr>\r\n<tr align=\"center\">\r\n<td style=\"height: 34px\">Sulfide<\/td>\r\n<td>H<sub>3<\/sub>C-S-CH<sub>3<\/sub><\/td>\r\n<td>Dimethyl sulfid<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<div id=\"section_12\">\r\n\r\n\r\n<h3 class=\"editable\">Functional Groups with Multiple Bonds to Heteroatoms<\/h3>\r\n<\/div>\r\n<table style=\"width: 90%\" border=\"0\">\r\n<thead>\r\n<tr>\r\n<th style=\"height: 20px;width: 20%\" scope=\"col\"><strong>Group Formula<\/strong><\/th>\r\n<th style=\"width: 18%\" scope=\"col\"><strong>Class Name<\/strong><\/th>\r\n<th style=\"width: 18%\" scope=\"col\"><strong>Specific Example<\/strong><\/th>\r\n<th style=\"width: 22%\" scope=\"col\"><strong>IUPAC Name<\/strong><\/th>\r\n<th style=\"width: 22%\" scope=\"col\"><strong>Common Name<\/strong><\/th>\r\n<\/tr>\r\n<\/thead>\r\n<tbody>\r\n<tr align=\"center\">\r\n<td rowspan=\"8\" valign=\"top\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210817\/funct3.gif\" alt=\"image\" \/><\/td>\r\n<td style=\"height: 34px\">Nitrile<\/td>\r\n<td>H<sub>3<\/sub>C-CN<\/td>\r\n<td>Ethanenitrile<\/td>\r\n<td>Acetonitrile<\/td>\r\n<\/tr>\r\n<tr align=\"center\">\r\n<td style=\"height: 72px\">Aldehyde<\/td>\r\n<td>H<sub>3<\/sub>CCHO<\/td>\r\n<td>Ethanal<\/td>\r\n<td>Acetaldehyde<\/td>\r\n<\/tr>\r\n<tr align=\"center\">\r\n<td style=\"height: 68px\">Ketone<\/td>\r\n<td>H<sub>3<\/sub>CCOCH<sub>3<\/sub><\/td>\r\n<td>Propanone<\/td>\r\n<td>Acetone<\/td>\r\n<\/tr>\r\n<tr align=\"center\">\r\n<td style=\"height: 66px\">Carboxylic Acid<\/td>\r\n<td>H<sub>3<\/sub>CCO<sub>2<\/sub>H<\/td>\r\n<td>Ethanoic Acid<\/td>\r\n<td>Acetic acid<\/td>\r\n<\/tr>\r\n<tr align=\"center\">\r\n<td style=\"height: 66px\">Ester<\/td>\r\n<td>H<sub>3<\/sub>CCO<sub>2<\/sub>CH<sub>2<\/sub>CH<sub>3<\/sub><\/td>\r\n<td>Ethyl ethanoate<\/td>\r\n<td>Ethyl acetate<\/td>\r\n<\/tr>\r\n<tr align=\"center\">\r\n<td style=\"height: 74px\">Acid Halide<\/td>\r\n<td>H<sub>3<\/sub>CCOCl<\/td>\r\n<td>Ethanoyl chloride<\/td>\r\n<td>Acetyl chloride<\/td>\r\n<\/tr>\r\n<tr align=\"center\">\r\n<td style=\"height: 88px\">Amide<\/td>\r\n<td>H<sub>3<\/sub>CCON(CH<sub>3<\/sub>)<sub>2<\/sub><\/td>\r\n<td>N,N-Dimethylethanamide<\/td>\r\n<td>N,N-Dimethylacetamide<\/td>\r\n<\/tr>\r\n<tr align=\"center\">\r\n<td style=\"height: 116px\">Acid Anhydride<\/td>\r\n<td>(H<sub>3<\/sub>CCO)<sub>2<\/sub>O<\/td>\r\n<td>Ethanoic anhydride<\/td>\r\n<td>Acetic anhydride<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<div id=\"section_13\">\r\n\r\n\r\n<div class=\"textbox exercises\">\r\n<h3>Exercises<\/h3>\r\n<div id=\"s61690\">\r\n<div>\r\n\r\n\r\n<h3 id=\"Questions-61690\">Question<\/h3>\r\n<span><span>The following is the molecule for ATP, or the molecule responsible for energy in human cells. Identify the functional groups for ATP.<\/span><\/span>\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210819\/3-1qu.png\" alt=\"\" width=\"505\" height=\"193\" \/>\r\n\r\n<\/div>\r\n<div>\r\n\r\n\r\n<h3 id=\"Solutions-61690\">Solution<\/h3>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210822\/3.1.png\" alt=\"\" width=\"565\" height=\"247\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n\r\n\r\n<\/div>\r\n<div id=\"section_14\">\r\n\r\n\r\n<h3 class=\"editable\">Contributors<\/h3>\r\n<ul>\r\n \t<li><a class=\"external\" title=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" href=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" target=\"_blank\" rel=\"external nofollow noopener\">Dr. Dietmar Kennepohl<\/a> FCIC (Professor of Chemistry, <a class=\"external\" title=\"http:\/\/www.athabascau.ca\/\" href=\"http:\/\/www.athabascau.ca\/\" target=\"_blank\" rel=\"external nofollow noopener\">Athabasca University<\/a>)<\/li>\r\n \t<li>Prof. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)<\/li>\r\n \t<li><a title=\"Organic_Chemistry_With_a_Biological_Emphasis\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry_Textbook_Maps\/Map%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)\" rel=\"internal\">Organic Chemistry With a Biological Emphasis <\/a>by\u00a0<a class=\"external\" title=\"http:\/\/facultypages.morris.umn.edu\/~soderbt\/\" href=\"http:\/\/facultypages.morris.umn.edu\/%7Esoderbt\/\" target=\"_blank\" rel=\"external nofollow noopener\">Tim Soderberg<\/a>\u00a0(University of Minnesota, Morris)<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>","rendered":"<div class=\"elm-header\"><\/div>\n<div id=\"elm-main-content\" class=\"elm-content-container\">\n<div>\n<div id=\"skills\">\n<div class=\"textbox learning-objectives\">\n<h3>Objectives<\/h3>\n<p>After completing this section, you should be able to<\/p>\n<ol>\n<li>explain why the properties of a given organic compound are largely dependent on the functional group or groups present in the compound.<\/li>\n<li>identify the functional groups present in each of the following compound types: alkenes, alkynes, arenes, (alkyl and aryl) halides, alcohols, ethers, aldehydes, ketones, esters, carboxylic acids, (carboxylic) acid chlorides, amides, amines, nitriles, nitro compounds, sulfides and sulfoxides.<\/li>\n<li>identify the functional groups present in an organic compound, given its structure.<\/li>\n<li>Given the structure of an organic compound containing a single functional group, identify which of the compound types listed under Objective 2, above, it belongs to.<\/li>\n<li>draw the structure of a simple example of each of the compound types listed in Objective 2.<\/li>\n<\/ol>\n<\/div>\n<div class=\"textbox key-takeaways\">\n<h3>Key Terms<\/h3>\n<div>\n<p>Make certain that you can define, and use in context, the key term below.<\/p>\n<ul>\n<li>functional group<\/li>\n<\/ul>\n<\/div>\n<\/div>\n<div class=\"textbox\">\n<div id=\"note\">\n<h3 class=\"boxtitle\">Study Notes<\/h3>\n<p>The concept of functional groups is a very important one. We expect that you will need to refer back to tables at the end of Section 3.1 quite frequently at first, as it is not really feasible to learn the names and structures of all the functional groups and compound types at one sitting. Gradually they will become familiar, and eventually you will recognize them automatically.<\/p>\n<\/div>\n<\/div>\n<\/div>\n<p><strong>Functional groups<\/strong> are atoms or small groups of atoms (two to four) that exhibit a characteristic reactivity. A particular functional group will almost always display its characteristic chemical behavior when it is present in a compound. Because of their importance in understanding organic chemistry, functional groups have characteristic names that often carry over in the naming of individual compounds incorporating specific groups<\/p>\n<p>As we progress in our study of organic chemistry, it will become extremely important to be able to quickly recognize the most common functional groups, because they are the key structural elements that define how organic molecules react.\u00a0For now, we will only worry about drawing and recognizing each functional group, as depicted by Lewis and line structures.\u00a0Much of the remainder of your study of organic chemistry will be taken up with learning about how the different functional groups tend to behave in organic reactions.<\/p>\n<div id=\"section_1\">\n<h3 class=\"editable\">Hydrocarbons and halides<\/h3>\n<p>We have already seen some examples of very common functional groups: ethene, for example, contains a carbon-carbon double bond.\u00a0This double bond is referred to, in the functional group terminology, as an <strong>alkene<\/strong>.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210723\/image085.png\" alt=\"image080.png\" width=\"412\" height=\"130\" \/><\/p>\n<p>The carbon-carbon triple bond in ethyne is the simplest example of an <strong>alkyne<\/strong> function group.<\/p>\n<p>What about ethane?\u00a0All we see in this molecule is carbon-hydrogen and carbon-carbon single bonds, so in a sense we can think of ethane as lacking a functional group entirely.\u00a0However,\u00a0we do have a general name for this \u2018default\u2019 carbon bonding pattern: molecules or parts of molecules containing only carbon-hydrogen and carbon-carbon single bonds are referred to as <strong>alkanes<\/strong>. If the carbon of an alkane is bonded to a halogen, the group is now referred to as a <a title=\"3.1 Functional Groups\" href=\"https:\/\/chem.libretexts.org\/LibreTexts\/Athabasca_University\/Chemistry_350%3A_Organic_Chemistry_I\/Chapter_3%3A_Organic_Compounds%3A_Alkanes_and_Their_Stereochemistry\/3.1_Functional_Groups\" rel=\"internal\"><strong>haloalkane<\/strong> <\/a>(fluoroalkane, chloroalkane, etc.).\u00a0 Chloroform, CHCl<sub>3<\/sub>, is an example of a simple haloalkane.<\/p>\n<\/div>\n<div id=\"section_2\">\n<h3 class=\"editable\">Alcohols and Thiols<\/h3>\n<p>We have already seen the simplest possible example of an <strong>alcohol<\/strong> functional group in methanol.\u00a0 In the alcohol functional group, a carbon is single-bonded to an OH group (this OH group, by itself, is referred to as a <strong>hydroxyl<\/strong>). If the central carbon in an alcohol is bonded to only one other carbon, we call the group a primary alcohol.\u00a0 In secondary alcohols and tertiary alcohols, the central carbon is bonded to two and three carbons, respectively. Methanol, of course, is in class by itself in this respect.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210725\/image087.png\" alt=\"image082.png\" width=\"598\" height=\"102\" \/><\/p>\n<p>The sulfur analog of an alcohol is called a <strong>thiol<\/strong> (the prefix <em>thio<\/em>, derived from the Greek, refers to sulfur).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210728\/image089.png\" alt=\"image084.png\" width=\"462\" height=\"102\" \/><\/p>\n<p>In an <strong>ether<\/strong> functional group, a central oxygen is bonded to two carbons. Below are the line and Lewis structures of diethyl ether, a common laboratory solvent and also one of the first medical anaesthesia agents.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210731\/image091.png\" alt=\"image086.png\" width=\"332\" height=\"75\" \/><\/p>\n<p>In <strong>sulfides<\/strong>, the oxygen atom of an ether has been replaced by a sulfur atom.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210733\/image093.png\" alt=\"image088.png\" width=\"228\" height=\"70\" \/><\/p>\n<\/div>\n<div id=\"section_3\">\n<h3 class=\"editable\">Amines and Phosphates<\/h3>\n<p>Ammonia is the simplest example of a functional group called <strong>amines<\/strong>.\u00a0 Just as there are primary, secondary, and tertiary alcohols, there are primary, secondary, and tertiary amines.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210736\/image095.png\" alt=\"image090.png\" width=\"535\" height=\"87\" \/><\/p>\n<p>One of the most important properties of amines is that they are basic, and are readily protonated to form <strong>ammonium<\/strong> cations.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210738\/image097.png\" alt=\"image092.png\" width=\"270\" height=\"103\" \/><\/p>\n<p>Phosphorus is a very important element in biological organic chemistry, and is found as the central atom in the <strong>phosphate<\/strong> group. Many biological organic molecules contain phosphate, diphosphate, and triphosphate groups, which are linked to a carbon atom by the <strong>phosphate ester<\/strong> functionality.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210741\/image099.png\" alt=\"image094.png\" width=\"597\" height=\"152\" \/><\/p>\n<p>Because phosphates are so abundant in biological organic chemistry, it is convenient to depict them with the abbreviation &#8216;P&#8217;.\u00a0Notice that this &#8216;P&#8217; abbreviation includes the oxygen atoms and negative charges associated with the phosphate groups.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210743\/image101.png\" alt=\"image096.png\" width=\"270\" height=\"118\" \/><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210745\/image103.png\" alt=\"image098.png\" width=\"438\" height=\"92\" \/><\/p>\n<\/div>\n<div id=\"section_4\">\n<h3 class=\"editable\">Carbonyl Containing Functional Groups<\/h3>\n<div id=\"section_5\">\n<h4 class=\"editable\">Aldehydes and Ketones<\/h4>\n<p>There are a number of functional groups that contain a carbon-oxygen double bond, which is commonly referred to as a <strong>carbonyl<\/strong>.\u00a0<strong>Ketones<\/strong> and <strong>aldehydes<\/strong> are two closely related carbonyl-based functional groups that react in very similar ways.\u00a0In a ketone, the carbon atom of a carbonyl is bonded to two other carbons. In an aldehyde, the carbonyl carbon is bonded on one side to a hydrogen, and on the other side to a carbon.\u00a0The exception to this definition is formaldehyde, in which the carbonyl carbon has bonds to two hydrogens.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210748\/image105.png\" alt=\"image100.png\" width=\"400\" height=\"112\" \/><\/p>\n<p>Molecules with carbon-nitrogen double bonds are called <strong>imines<\/strong>, or <strong>Schiff bases<\/strong>.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210750\/image107.png\" alt=\"image102.png\" width=\"105\" height=\"122\" \/><\/p>\n<\/div>\n<div id=\"section_6\">\n<h4 class=\"editable\">Carboxylic acids and acid derivatives<\/h4>\n<p>If a carbonyl carbon is bonded on one side to a carbon (or hydrogen) and on the other side to a <strong>heteroatom<\/strong> (in organic chemistry, this term generally refers to oxygen, nitrogen, sulfur, or one of the halogens), the functional group is considered to be one of the \u2018<strong>carboxylic acid derivatives\u2019<\/strong>, a designation that describes a grouping of several functional groups.\u00a0The eponymous member of this grouping is the <strong>carboxylic acid<\/strong> functional group, in which the carbonyl is bonded to a hydroxyl (OH) group.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210752\/image109.png\" alt=\"image104.png\" width=\"242\" height=\"117\" \/><\/p>\n<p>As the name implies, carboxylic acids are acidic, meaning that they are readily deprotonated to form the conjugate base form, called a <strong>carboxylate<\/strong> (much more about carboxylic acids in the acid-base chapter!).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210754\/image111.png\" alt=\"image106.png\" width=\"222\" height=\"97\" \/><\/p>\n<p>In <strong>amides<\/strong>, the carbonyl carbon is bonded to a nitrogen.\u00a0The nitrogen in an amide can be bonded either to hydrogens, to carbons, or to both. Another way of thinking of an amide is that it is a carbonyl bonded to an amine.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210756\/image113.png\" alt=\"image108.png\" width=\"432\" height=\"93\" \/><\/p>\n<p>In <strong>esters<\/strong>, the carbonyl carbon is bonded to an oxygen which is itself bonded to another carbon. Another way of thinking of an ester is that it is a carbonyl bonded to an alcohol.\u00a0<strong>Thioesters<\/strong> are similar to esters, except a sulfur is in place of the oxygen.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210758\/image115.png\" alt=\"image110.png\" width=\"287\" height=\"90\" \/><\/p>\n<p>In an <strong>acyl phosphate<\/strong>, the carbonyl carbon is bonded to the oxygen of a phosphate, and in an <strong>acid chloride<\/strong>, the carbonyl carbon is bonded to a chlorine.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210801\/image117.png\" alt=\"image112.png\" width=\"328\" height=\"115\" \/><\/p>\n<p>Finally, in a <strong>nitrile<\/strong> group, a carbon is triple-bonded to a nitrogen.\u00a0Nitriles are also often referred to as <strong>cyano<\/strong> groups.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210804\/image119.png\" alt=\"image114.png\" width=\"93\" height=\"53\" \/><\/p>\n<p>A single compound often contains several functional groups. The six-carbon sugar molecules glucose and fructose, for example, contain aldehyde and ketone groups, respectively, and both contain five alcohol groups (a compound with several alcohol groups is often referred to as a \u2018<strong>polyol\u2019<\/strong>).<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210805\/image121.png\" alt=\"image121.png\" width=\"348px\" height=\"113px\" \/><\/p>\n<p>Capsaicin, the compound responsible for the heat in hot peppers, contains phenol, ether, amide, and alkene functional groups.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210807\/image123.png\" alt=\"image116.png\" width=\"400\" height=\"142\" \/><\/p>\n<p>The male sex hormone testosterone contains ketone, alkene, and secondary alcohol groups, while acetylsalicylic acid (aspirin) contains aromatic, carboxylic acid, and ester groups.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210809\/image125.png\" alt=\"image118.png\" width=\"445\" height=\"185\" \/><\/p>\n<p>While not in any way a complete list, this section has covered most of the important functional groups that we will encounter in biological and laboratory organic chemistry. The table on the inside back cover provides a summary of all of the groups listed in this section, plus a few more that will be introduced later in the text.<\/p>\n<div style=\"margin: auto\">\n<div id=\"section_7\">\n<div class=\"textbox exercises\">\n<h3>Exercises<\/h3>\n<div id=\"section_6\">\n<div style=\"margin: auto\">\n<div id=\"section_7\">\n<h3 class=\"editable\">Problems<\/h3>\n<\/div>\n<\/div>\n<p>1: Identify the functional groups in the following organic compounds. State whether alcohols and amines are primary, secondary, or tertiary.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210812\/image127.png\" alt=\"image120.png\" width=\"537\" height=\"355\" \/><\/p>\n<p>2: Draw one example each (there are many possible correct answers) of compounds fitting the descriptions below, using line structures.\u00a0 Be sure to designate the location of all non-zero formal charges. All atoms should have complete octets (phosphorus may exceed the octet rule).<\/p>\n<ol start=\"1\">\n<li>a compound with molecular formula C<sub>6<\/sub>H<sub>11<\/sub>NO that includes alkene, secondary amine, and primary alcohol functional groups<\/li>\n<li>an ion with molecular formula C<sub>3<\/sub>H<sub>5<\/sub>O<sub>6<\/sub>P <sup>2-<\/sup> that\u00a0 includes aldehyde, secondary alcohol, and phosphate functional groups.<\/li>\n<li>A compound with molecular formula C<sub>6<\/sub>H<sub>9<\/sub>NO that has an amide functional group, and does <em>not<\/em> have an alkene group.<\/li>\n<\/ol>\n<\/div>\n<div id=\"section_8\">\n<h4 class=\"editable\">Solution<\/h4>\n<p>1:<\/p>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q347160\">Show Answer<\/span><\/p>\n<div id=\"q347160\" class=\"hidden-answer\" style=\"display: none\">a) carboxylate, sulfide, aromatic, two amide groups (one of which is cyclic)<\/p>\n<p>b) tertiary alcohol, thioester<\/p>\n<p>c) carboxylate, ketone<\/p>\n<p>d) ether, primary amine, alkene<\/p><\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_9\">\n<h2 class=\"editable\">Functional Group Tables<\/h2>\n<div id=\"section_10\">\n<h3 class=\"editable\">Exclusively Carbon Functional Groups<\/h3>\n<table style=\"width: 90%\">\n<thead>\n<tr>\n<th style=\"width: 20%\" scope=\"col\"><strong>Group Formula<\/strong><\/th>\n<th style=\"width: 20%\" scope=\"col\"><strong>Class Name<\/strong><\/th>\n<th style=\"width: 20%\" scope=\"col\"><strong>Specific Example<\/strong><\/th>\n<th style=\"width: 20%\" scope=\"col\"><strong>IUPAC Name<\/strong><\/th>\n<th style=\"width: 20%\" scope=\"col\"><strong>Common Name<\/strong><\/th>\n<\/tr>\n<\/thead>\n<tbody>\n<tr align=\"center\" valign=\"middle\">\n<td style=\"height: 198px;width: 112px\" rowspan=\"3\" valign=\"top\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210814\/funct1.gif\" alt=\"image\" \/><\/td>\n<td style=\"height: 50px\">Alkene<\/td>\n<td>H<sub>2<\/sub>C=CH<sub>2<\/sub><\/td>\n<td>Ethene<\/td>\n<td>Ethylene<\/td>\n<\/tr>\n<tr align=\"center\" valign=\"middle\">\n<td style=\"height: 54px\">Alkyne<\/td>\n<td>HC\u2261CH<\/td>\n<td>Ethyne<\/td>\n<td>Acetylene<\/td>\n<\/tr>\n<tr align=\"center\" valign=\"middle\">\n<td style=\"height: 94px\">Arene<\/td>\n<td>C<sub>6<\/sub>H<sub>6<\/sub><\/td>\n<td>Benzene<\/td>\n<td>Benzene<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<div id=\"section_11\">\n<h3 class=\"editable\">Functional Groups with Single Bonds to Heteroatoms<\/h3>\n<\/div>\n<table style=\"width: 90%\">\n<thead>\n<tr>\n<th style=\"height: 17px;width: 20%\" scope=\"col\"><strong>Group Formula<\/strong><\/th>\n<th style=\"width: 20%\" scope=\"col\"><strong>Class Name<\/strong><\/th>\n<th style=\"width: 20%\" scope=\"col\"><strong>Specific Example<\/strong><\/th>\n<th style=\"width: 20%\" scope=\"col\"><strong>IUPAC Name<\/strong><\/th>\n<th style=\"width: 20%\" scope=\"col\"><strong>Common Name<\/strong><\/th>\n<\/tr>\n<\/thead>\n<tbody>\n<tr align=\"center\">\n<td style=\"height: 110px;width: 64px\" rowspan=\"3\" valign=\"top\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210815\/funct2a.gif\" alt=\"image\" \/><\/td>\n<td style=\"height: 37px\">Halide<\/td>\n<td>H<sub>3<\/sub>C-I<\/td>\n<td>Iodomethane<\/td>\n<td>Methyl iodide<\/td>\n<\/tr>\n<tr align=\"center\">\n<td style=\"height: 37px\">Alcohol<\/td>\n<td>CH<sub>3<\/sub>CH<sub>2<\/sub>OH<\/td>\n<td>Ethanol<\/td>\n<td>Ethyl alcohol<\/td>\n<\/tr>\n<tr align=\"center\">\n<td style=\"height: 36px\">Ether<\/td>\n<td>CH<sub>3<\/sub>CH<sub>2<\/sub>OCH<sub>2<\/sub>CH<sub>3<\/sub><\/td>\n<td>Diethyl ether<\/td>\n<td>Ether<\/td>\n<\/tr>\n<tr align=\"center\">\n<td style=\"height: 168px;width: 72px\" rowspan=\"4\" valign=\"top\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210815\/funct2b.gif\" alt=\"image\" \/><\/td>\n<td style=\"height: 36px\">Amine<\/td>\n<td>H<sub>3<\/sub>C-NH<sub>2<\/sub><\/td>\n<td>Aminomethane<\/td>\n<td>Methylamine<\/td>\n<\/tr>\n<tr align=\"center\">\n<td style=\"height: 64px\">Nitro Compound<\/td>\n<td>H<sub>3<\/sub>C-NO<sub>2<\/sub><\/td>\n<td>Nitromethane<\/td>\n<td><\/td>\n<\/tr>\n<tr align=\"center\">\n<td style=\"height: 34px\">Thiol<\/td>\n<td>H<sub>3<\/sub>C-SH<\/td>\n<td>Methanethiol<\/td>\n<td>Methyl mercaptan<\/td>\n<\/tr>\n<tr align=\"center\">\n<td style=\"height: 34px\">Sulfide<\/td>\n<td>H<sub>3<\/sub>C-S-CH<sub>3<\/sub><\/td>\n<td>Dimethyl sulfid<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<div id=\"section_12\">\n<h3 class=\"editable\">Functional Groups with Multiple Bonds to Heteroatoms<\/h3>\n<\/div>\n<table style=\"width: 90%\">\n<thead>\n<tr>\n<th style=\"height: 20px;width: 20%\" scope=\"col\"><strong>Group Formula<\/strong><\/th>\n<th style=\"width: 18%\" scope=\"col\"><strong>Class Name<\/strong><\/th>\n<th style=\"width: 18%\" scope=\"col\"><strong>Specific Example<\/strong><\/th>\n<th style=\"width: 22%\" scope=\"col\"><strong>IUPAC Name<\/strong><\/th>\n<th style=\"width: 22%\" scope=\"col\"><strong>Common Name<\/strong><\/th>\n<\/tr>\n<\/thead>\n<tbody>\n<tr align=\"center\">\n<td rowspan=\"8\" valign=\"top\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210817\/funct3.gif\" alt=\"image\" \/><\/td>\n<td style=\"height: 34px\">Nitrile<\/td>\n<td>H<sub>3<\/sub>C-CN<\/td>\n<td>Ethanenitrile<\/td>\n<td>Acetonitrile<\/td>\n<\/tr>\n<tr align=\"center\">\n<td style=\"height: 72px\">Aldehyde<\/td>\n<td>H<sub>3<\/sub>CCHO<\/td>\n<td>Ethanal<\/td>\n<td>Acetaldehyde<\/td>\n<\/tr>\n<tr align=\"center\">\n<td style=\"height: 68px\">Ketone<\/td>\n<td>H<sub>3<\/sub>CCOCH<sub>3<\/sub><\/td>\n<td>Propanone<\/td>\n<td>Acetone<\/td>\n<\/tr>\n<tr align=\"center\">\n<td style=\"height: 66px\">Carboxylic Acid<\/td>\n<td>H<sub>3<\/sub>CCO<sub>2<\/sub>H<\/td>\n<td>Ethanoic Acid<\/td>\n<td>Acetic acid<\/td>\n<\/tr>\n<tr align=\"center\">\n<td style=\"height: 66px\">Ester<\/td>\n<td>H<sub>3<\/sub>CCO<sub>2<\/sub>CH<sub>2<\/sub>CH<sub>3<\/sub><\/td>\n<td>Ethyl ethanoate<\/td>\n<td>Ethyl acetate<\/td>\n<\/tr>\n<tr align=\"center\">\n<td style=\"height: 74px\">Acid Halide<\/td>\n<td>H<sub>3<\/sub>CCOCl<\/td>\n<td>Ethanoyl chloride<\/td>\n<td>Acetyl chloride<\/td>\n<\/tr>\n<tr align=\"center\">\n<td style=\"height: 88px\">Amide<\/td>\n<td>H<sub>3<\/sub>CCON(CH<sub>3<\/sub>)<sub>2<\/sub><\/td>\n<td>N,N-Dimethylethanamide<\/td>\n<td>N,N-Dimethylacetamide<\/td>\n<\/tr>\n<tr align=\"center\">\n<td style=\"height: 116px\">Acid Anhydride<\/td>\n<td>(H<sub>3<\/sub>CCO)<sub>2<\/sub>O<\/td>\n<td>Ethanoic anhydride<\/td>\n<td>Acetic anhydride<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<div id=\"section_13\">\n<div class=\"textbox exercises\">\n<h3>Exercises<\/h3>\n<div id=\"s61690\">\n<div>\n<h3 id=\"Questions-61690\">Question<\/h3>\n<p><span><span>The following is the molecule for ATP, or the molecule responsible for energy in human cells. Identify the functional groups for ATP.<\/span><\/span><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210819\/3-1qu.png\" alt=\"\" width=\"505\" height=\"193\" \/><\/p>\n<\/div>\n<div>\n<h3 id=\"Solutions-61690\">Solution<\/h3>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210822\/3.1.png\" alt=\"\" width=\"565\" height=\"247\" \/><\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_14\">\n<h3 class=\"editable\">Contributors<\/h3>\n<ul>\n<li><a class=\"external\" title=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" href=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" target=\"_blank\" rel=\"external nofollow noopener\">Dr. Dietmar Kennepohl<\/a> FCIC (Professor of Chemistry, <a class=\"external\" title=\"http:\/\/www.athabascau.ca\/\" href=\"http:\/\/www.athabascau.ca\/\" target=\"_blank\" rel=\"external nofollow noopener\">Athabasca University<\/a>)<\/li>\n<li>Prof. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)<\/li>\n<li><a title=\"Organic_Chemistry_With_a_Biological_Emphasis\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry_Textbook_Maps\/Map%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)\" rel=\"internal\">Organic Chemistry With a Biological Emphasis <\/a>by\u00a0<a class=\"external\" title=\"http:\/\/facultypages.morris.umn.edu\/~soderbt\/\" href=\"http:\/\/facultypages.morris.umn.edu\/%7Esoderbt\/\" target=\"_blank\" rel=\"external nofollow noopener\">Tim Soderberg<\/a>\u00a0(University of Minnesota, Morris)<\/li>\n<\/ul>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n","protected":false},"author":311,"menu_order":1,"template":"","meta":{"_candela_citation":"[]","CANDELA_OUTCOMES_GUID":"","pb_show_title":"on","pb_short_title":"","pb_subtitle":"","pb_authors":[],"pb_section_license":""},"chapter-type":[],"contributor":[],"license":[],"class_list":["post-642","chapter","type-chapter","status-publish","hentry"],"part":21,"_links":{"self":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/642","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters"}],"about":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/types\/chapter"}],"author":[{"embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/users\/311"}],"version-history":[{"count":4,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/642\/revisions"}],"predecessor-version":[{"id":2106,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/642\/revisions\/2106"}],"part":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/parts\/21"}],"metadata":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/642\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/media?parent=642"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapter-type?post=642"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/contributor?post=642"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/license?post=642"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}