{"id":1447,"date":"2018-03-21T15:08:35","date_gmt":"2018-03-21T15:08:35","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-orgbiochemistry\/chapter\/aldehydes-and-ketones-structure-and-names\/"},"modified":"2018-10-31T15:26:05","modified_gmt":"2018-10-31T15:26:05","slug":"aldehydes-and-ketones-structure-and-names","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-monroecc-orgbiochemistry\/chapter\/aldehydes-and-ketones-structure-and-names\/","title":{"raw":"14.9 Aldehydes and Ketones: Structure and Names","rendered":"14.9 Aldehydes and Ketones: Structure and Names"},"content":{"raw":"<div id=\"navbar-top\" class=\"navbar\"><\/div>\r\n<div id=\"book-content\">\r\n<div id=\"gob-ch14_s09\" class=\"section\" xml:lang=\"en\">\r\n<div id=\"gob-ch14_s09_n01\" class=\"learning_objectives editable block\">\r\n<div class=\"textbox learning-objectives\">\r\n<h3 class=\"title\">Learning Objectives<\/h3>\r\n<ol id=\"gob-ch14_s09_l01\" class=\"orderedlist\">\r\n \t<li>Identify the general structure for an aldehyde and a ketone.<\/li>\r\n \t<li>Use common names to name aldehydes and ketones.<\/li>\r\n \t<li>Use the IUPAC system to name aldehydes and ketones.<\/li>\r\n<\/ol>\r\n<\/div>\r\n<span style=\"font-size: 1rem;text-align: initial\">The next functional group we consider, the <\/span><span class=\"margin_term\" style=\"font-size: 1rem;text-align: initial\"><span class=\"glossterm\">carbonyl group<\/span><\/span><span style=\"font-size: 1rem;text-align: initial\">, has a carbon-to-oxygen double bond.<\/span>\r\n\r\n<\/div>\r\n<div class=\"informalfigure large block\"><img class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150709\/c99afd71e60c6d951c0a506e18d676e2.jpg\" alt=\"image\" \/><\/div>\r\n<p id=\"gob-ch14_s09_p02\" class=\"para editable block\">Carbonyl groups define two related families of organic compounds: the aldehydes and the ketones.\u00a0 The carbonyl group is also found in Carboxylic acids, esters, and amides, which will be discussed in other sections.<\/p>\r\n\r\n<div id=\"gob-ch14_s09_n02\" class=\"callout editable block\">\r\n<div class=\"textbox\">\r\n<h3 class=\"title\">Note<\/h3>\r\n<p id=\"gob-ch14_s09_p03\" class=\"para\">The carbonyl group is ubiquitous in biological compounds. It is found in carbohydrates, fats, proteins, nucleic acids, hormones, and vitamins\u2014organic compounds critical to living systems.<\/p>\r\n\r\n<\/div>\r\n<\/div>\r\n<p id=\"gob-ch14_s09_p04\" class=\"para editable block\">In a <span class=\"margin_term\"><span class=\"glossterm\">ketone<\/span><\/span>, two carbon groups are attached to the carbonyl carbon atom. The following general formulas, in which R represents an alkyl group and Ar stands for an aryl group, represent ketones.<\/p>\r\n\r\n<div class=\"informalfigure large block\"><img class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150712\/3a2c2bc1cdf2ee3389d8e891bd649eb1.jpg\" alt=\"image\" \/><\/div>\r\n<p id=\"gob-ch14_s09_p05\" class=\"para editable block\">In an <span class=\"margin_term\"><span class=\"glossterm\">aldehyde<\/span><\/span>, at least one of the attached groups must be a hydrogen atom. The following compounds are aldehydes:<\/p>\r\n\r\n<div class=\"informalfigure large block\"><img class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150714\/aea4705b99aaa721f6011c448cb1e67d.jpg\" alt=\"image\" \/><\/div>\r\n<p id=\"gob-ch14_s09_p06\" class=\"para editable block\">In condensed formulas, we use CHO to identify an aldehyde rather than COH, which might be confused with an alcohol. This follows the general rule that in condensed structural formulas H comes after the atom it is attached to (usually C, N, or O).<\/p>\r\n\r\n<div class=\"informalfigure large block\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150717\/4b27089fc7763d264d34c0dcd4c13dd6.jpg\" alt=\"image\" \/><\/div>\r\n<p id=\"gob-ch14_s09_p07\" class=\"para editable block\">The carbon-to-oxygen double bond is not shown but understood to be present.<\/p>\r\n<p id=\"gob-ch14_s09_p08\" class=\"para editable block\">Because they contain the same functional group, aldehydes and ketones share many common properties, but they still differ enough to warrant their classification into two families.<\/p>\r\n\r\n<div id=\"gob-ch14_s09_s01\" class=\"section\">\r\n<h2 class=\"title editable block\">Naming Aldehydes and Ketones<\/h2>\r\n<p id=\"gob-ch14_s09_s01_p01\" class=\"para editable block\">Both common and International Union of Pure and Applied Chemistry (IUPAC) names are frequently used for aldehydes and ketones, with common names predominating for the lower homologs. The common names of aldehydes are taken from the names of the acids into which the aldehydes can be converted by oxidation. (For more information about carboxylic acids, see <a class=\"xref\" href=\"..\/suny-orgbiochemistry\/chapter\/introduction-15\">Chapter 15 \"Organic Acids and Bases and Some of Their Derivatives\"<\/a>, <a class=\"xref\" href=\"gob-ch15_s02#gob-ch15_s02\">Section 15.2 \"Carboxylic Acids: Structures and Names\"<\/a> through <a class=\"xref\" href=\"gob-ch15_s04#gob-ch15_s04\">Section 15.4 \"Physical Properties of Carboxylic Acids\"<\/a>.)<\/p>\r\n\r\n<div class=\"informalfigure large block\"><img class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150720\/a4342afac9b9fa33eef54dbef9827067.jpg\" alt=\"image\" \/><\/div>\r\n<div id=\"gob-ch14_s09_s01_n01\" class=\"callout editable block\">\r\n<div class=\"textbox\">\r\n<h3 class=\"title\">Note<\/h3>\r\n<p id=\"gob-ch14_s09_s01_p02\" class=\"para\">The stems for the common names of the first four aldehydes are as follows:<\/p>\r\n\r\n<ul id=\"gob-ch14_s09_s01_l01\" class=\"itemizedlist\">\r\n \t<li>1 carbon atom: <em class=\"emphasis\">form<\/em>-<\/li>\r\n \t<li>2 carbon atoms: <em class=\"emphasis\">acet<\/em>-<\/li>\r\n \t<li>3 carbon atoms: <em class=\"emphasis\">propion<\/em>-<\/li>\r\n \t<li>4 carbon atoms: <em class=\"emphasis\">butyr<\/em>-<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>\r\n<p id=\"gob-ch14_s09_s01_p03\" class=\"para editable block\">Because the carbonyl group in a ketone must be attached to two carbon groups, the simplest ketone has three carbon atoms. It is widely known as <em class=\"emphasis\">acetone<\/em>, a unique name unrelated to other common names for ketones.<\/p>\r\n\r\n<div class=\"informalfigure large block\"><img class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150723\/e2edc94ebd7f46df06b99e74ed3bd654.jpg\" alt=\"image\" \/><\/div>\r\n<p id=\"gob-ch14_s09_s01_p04\" class=\"para editable block\">Generally, the common names of ketones consist of the names of the groups attached to the carbonyl group, followed by the word <em class=\"emphasis\">ketone<\/em>. (Note the similarity to the naming of ethers.) Another name for acetone, then, is <em class=\"emphasis\">dimethyl ketone.<\/em> The ketone with four carbon atoms is ethyl methyl ketone.<\/p>\r\n\r\n<div class=\"informalfigure large block\"><img class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150726\/b6b55f1bdf24ab08ba511096637efd9f.jpg\" alt=\"image\" \/><\/div>\r\n<div id=\"gob-ch14_s09_s01_n02\" class=\"exercises editable block\">\r\n<h3 class=\"title\">Example 6<\/h3>\r\n<p id=\"gob-ch14_s09_s01_p05\" class=\"para\">Classify each compound as an aldehyde or a ketone. Give the common name for each ketone.<\/p>\r\n\r\n<ol id=\"gob-ch14_s09_s01_l02\" class=\"orderedlist\">\r\n \t<li>\r\n<div class=\"informalfigure large\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150729\/936d06564f4a5e15df10dc4018a6d4b8.jpg\" alt=\"image\" \/><\/div><\/li>\r\n \t<li>\r\n<div class=\"informalfigure large\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150732\/5a3e5cf375b47a091fd1db2c837b30f2.jpg\" alt=\"image\" \/><\/div><\/li>\r\n \t<li>\r\n<div class=\"informalfigure large\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150735\/d3d0cb767cda253ed0e3a6d63b3b1219.jpg\" alt=\"image\" \/><\/div><\/li>\r\n<\/ol>\r\n<p class=\"simpara\">Solution<\/p>\r\n\r\n<ol id=\"gob-ch14_s09_s01_l03\" class=\"orderedlist\">\r\n \t<li>This compound has the carbonyl group on an end carbon atom, so it is an aldehyde.<\/li>\r\n \t<li>This compound has the carbonyl group on an interior carbon atom, so it is a ketone. Both alkyl groups are propyl groups. The name is therefore dipropyl ketone.<\/li>\r\n \t<li>This compound has the carbonyl group between two alkyl groups, so it is a ketone. One alkyl group has three carbon atoms and is attached by the middle carbon atom; it is an isopropyl group. A group with one carbon atom is a methyl group. The name is therefore isopropyl methyl ketone.<\/li>\r\n<\/ol>\r\n<\/div>\r\n<div id=\"gob-ch14_s09_qs01\" class=\"qandaset block\">\r\n<div class=\"textbox shaded\">\r\n<h3 class=\"title\">Skill-Building Exercise<\/h3>\r\n<p class=\"title\">Classify each compound as an aldehyde or a ketone. Give the common name for each ketone.<\/p>\r\n\r\n<ol id=\"gob-ch14_s09_qs01_qd01\" class=\"qandadiv\">\r\n \t<li id=\"gob-ch14_s09_qs01_qd01_qa01\" class=\"qandaentry\">\r\n<div class=\"question\">\r\n<div class=\"informalfigure large\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150737\/d564bb3d2391b00c9de1b892938ffa84.jpg\" alt=\"image\" \/><\/div>\r\n<\/div><\/li>\r\n \t<li id=\"gob-ch14_s09_qs01_qd01_qa02\" class=\"qandaentry\">\r\n<div class=\"question\">\r\n<div class=\"informalfigure large\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150740\/5a5a2ed8e7caf01167dad9765e57218f.jpg\" alt=\"image\" \/><\/div>\r\n<\/div><\/li>\r\n \t<li id=\"gob-ch14_s09_qs01_qd01_qa03\" class=\"qandaentry\">\r\n<div class=\"question\">\r\n<div class=\"informalfigure large\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150743\/60e1bd998fac7ad65662551494071e4b.jpg\" alt=\"image\" \/><\/div>\r\n<\/div><\/li>\r\n<\/ol>\r\n<\/div>\r\n<span style=\"font-size: 1rem;text-align: initial\">Here are some simple IUPAC rules for naming aldehydes and ketones:<\/span>\r\n\r\n<\/div>\r\n<ol id=\"gob-ch14_s09_s01_l05\" class=\"orderedlist editable block\">\r\n \t<li>The stem names of aldehydes and ketones are derived from those of the parent alkanes, defined by the longest continuous chain (LCC) of carbon atoms that contains the functional group.<\/li>\r\n \t<li>For an aldehyde, drop the -<em class=\"emphasis\">e<\/em> from the alkane name and add the ending -<em class=\"emphasis\">al<\/em>. Methanal is the IUPAC name for formaldehyde, and ethanal is the name for acetaldehyde.<\/li>\r\n \t<li>For a ketone, drop the -<em class=\"emphasis\">e<\/em> from the alkane name and add the ending -<em class=\"emphasis\">one<\/em>. Propanone is the IUPAC name for acetone, and butanone is the name for ethyl methyl ketone.<\/li>\r\n \t<li>To indicate the position of a substituent on an aldehyde, the carbonyl carbon atom is always considered to be C1; it is unnecessary to designate this group by number.<\/li>\r\n \t<li>To indicate the position of a substituent on a ketone, number the chain in the manner that gives the carbonyl carbon atom the lowest possible number. In cyclic ketones, it is understood that the carbonyl carbon atom is C1.<\/li>\r\n<\/ol>\r\n<div id=\"gob-ch14_s09_s01_n04\" class=\"exercises editable block\">\r\n<h3 class=\"title\">Example 7<\/h3>\r\n<p id=\"gob-ch14_s09_s01_p11\" class=\"para\">Give the IUPAC name for each compound.<\/p>\r\n\r\n<ol id=\"gob-ch14_s09_s01_l06\" class=\"orderedlist\">\r\n \t<li>\r\n<div class=\"informalfigure large\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150746\/f8433f746ceda879e02ec31aa113bfe8.jpg\" alt=\"image\" \/><\/div><\/li>\r\n \t<li>\r\n<div class=\"informalfigure large\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150749\/c3c5aa121cd09ded3ad9cecd905903a6.jpg\" alt=\"image\" \/><\/div><\/li>\r\n \t<li>\r\n<div class=\"informalfigure large\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150752\/7552c41ec3ff1d2181167793498bfffa.jpg\" alt=\"image\" \/><\/div><\/li>\r\n<\/ol>\r\n<p class=\"simpara\">Solution<\/p>\r\n\r\n<ol id=\"gob-ch14_s09_s01_l07\" class=\"orderedlist\">\r\n \t<li>There are five carbon atoms in the LCC. The methyl group (CH<sub class=\"subscript\">3<\/sub>) is a substituent on the second carbon atom of the chain; the aldehyde carbon atom is always C1. The name is derived from pentane. Dropping the -<em class=\"emphasis\">e<\/em> and adding the ending -<em class=\"emphasis\">al<\/em> gives pentanal. The methyl group on the second carbon atom makes the name 2-methylpentanal.<\/li>\r\n \t<li>There are five carbon atoms in the LCC. The carbonyl carbon atom is C3, and there are methyl groups on C2 and C4. The IUPAC name is 2,4-dimethyl-3-pentanone.<\/li>\r\n \t<li>There are six carbon atoms in the ring. The compound is cyclohexanone. No number is needed to indicate the position of the carbonyl group because all six carbon atoms are equivalent.<\/li>\r\n<\/ol>\r\n<\/div>\r\n<div id=\"gob-ch14_s09_qs02\" class=\"qandaset block\">\r\n<div class=\"textbox shaded\">\r\n<h3 class=\"title\">Skill-Building Exercise<\/h3>\r\n<p class=\"title\">Give the IUPAC name for each compound.<\/p>\r\n\r\n<ol id=\"gob-ch14_s09_qs02_qd01\" class=\"qandadiv\">\r\n \t<li id=\"gob-ch14_s09_qs02_qd01_qa01\" class=\"qandaentry\">\r\n<div class=\"question\">\r\n<div class=\"informalfigure large\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150755\/9d30dbb9670be9cabfbfd913d977def4.jpg\" alt=\"image\" \/><\/div>\r\n<\/div><\/li>\r\n \t<li id=\"gob-ch14_s09_qs02_qd01_qa02\" class=\"qandaentry\">\r\n<div class=\"question\">\r\n<div class=\"informalfigure large\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150758\/85e8f3cbaefd3cf6c6bce9bacc4ff59a.jpg\" alt=\"image\" \/><\/div>\r\n<\/div><\/li>\r\n \t<li id=\"gob-ch14_s09_qs02_qd01_qa03\" class=\"qandaentry\">\r\n<div class=\"question\">\r\n<div class=\"informalfigure large\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150800\/27452d4f63aa775eeb5f1df9964f74ba.jpg\" alt=\"image\" \/><\/div>\r\n<\/div><\/li>\r\n<\/ol>\r\n<\/div>\r\n<\/div>\r\n<div id=\"gob-ch14_s09_s01_n06\" class=\"exercises editable block\">\r\n<h3 class=\"title\">Example 8<\/h3>\r\n<p id=\"gob-ch14_s09_s01_p16\" class=\"para\">Draw the structure for each compound.<\/p>\r\n\r\n<ol id=\"gob-ch14_s09_s01_l09\" class=\"orderedlist\">\r\n \t<li>7-chlorooctanal<\/li>\r\n \t<li>4-methyl\u20133-hexanone<\/li>\r\n<\/ol>\r\n<p class=\"simpara\">Solution<\/p>\r\n\r\n<ol id=\"gob-ch14_s09_s01_l10\" class=\"orderedlist\">\r\n \t<li>\r\n<p class=\"para\">The <em class=\"emphasis\">octan<\/em>- part of the name tells us that the LCC has eight carbon atoms. There is a chlorine (Cl) atom on the seventh carbon atom; numbering from the carbonyl group and counting the carbonyl carbon atom as C1, we place the Cl atom on the seventh carbon atom.<\/p>\r\n\r\n<div class=\"informalfigure large\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150803\/4899969d52c9566dc6cbb8f70dd6daf5.jpg\" alt=\"image\" \/><\/div><\/li>\r\n \t<li>\r\n<p class=\"para\">The <em class=\"emphasis\">hexan<\/em>- part of the name tells us that the LCC has six carbon atoms. The 3 means that the carbonyl carbon atom is C3 in this chain, and the 4 tells us that there is a methyl (CH<sub class=\"subscript\">3<\/sub>) group at C4:<\/p>\r\n\r\n<div class=\"informalfigure large\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150806\/e0e0b6646c77c00b6d0ed135bab4ee70.jpg\" alt=\"image\" \/><\/div><\/li>\r\n<\/ol>\r\n<\/div>\r\n<div id=\"gob-ch14_s09_qs03\" class=\"qandaset block\">\r\n<div class=\"textbox shaded\">\r\n<h3 class=\"title\">Skill-Building Exercise<\/h3>\r\n<p class=\"title\">Draw the structure for each compound.<\/p>\r\n\r\n<ol id=\"gob-ch14_s09_qs03_qd01\" class=\"qandadiv\">\r\n \t<li id=\"gob-ch14_s09_qs03_qd01_qa01\" class=\"qandaentry\">\r\n<div class=\"question\">\r\n<p id=\"gob-ch14_s09_qs03_p02\" class=\"para\">5-bromo-3-iodoheptanal<\/p>\r\n\r\n<\/div><\/li>\r\n \t<li id=\"gob-ch14_s09_qs03_qd01_qa02\" class=\"qandaentry\">\r\n<div class=\"question\">\r\n<p id=\"gob-ch14_s09_qs03_p03\" class=\"para\">5-bromo-4-ethyl-2-heptanone<\/p>\r\n\r\n<\/div><\/li>\r\n<\/ol>\r\n<\/div>\r\n<\/div>\r\n<div id=\"gob-ch14_s09_qs04\" class=\"qandaset block\">\r\n<div class=\"textbox exercises\">\r\n<div id=\"gob-ch14_s09_qs04\" class=\"qandaset block\">\r\n<h3 class=\"title\">Concept Review Exercises<\/h3>\r\n<ol id=\"gob-ch14_s09_qs04_qd01\" class=\"qandadiv\">\r\n \t<li id=\"gob-ch14_s09_qs04_qd01_qa01\" class=\"qandaentry\">\r\n<div class=\"question\">\r\n<p id=\"gob-ch14_s09_qs04_p01\" class=\"para\">Give the structure and IUPAC name for the compound that has the common name <em class=\"emphasis\">m<\/em>-bromobenzaldehyde (see <a class=\"xref\" href=\"gob-ch14_s10#gob-ch14_s10_s02_f01\">Figure 14.6 \"Some Interesting Aldehydes\"<\/a> for the structure of benzaldehyde).<\/p>\r\n\r\n<\/div><\/li>\r\n \t<li id=\"gob-ch14_s09_qs04_qd01_qa02\" class=\"qandaentry\">\r\n<div class=\"question\">\r\n<p id=\"gob-ch14_s09_qs04_p03\" class=\"para\">Give the IUPAC name for glyceraldehyde, (HOCH<sub class=\"subscript\">2<\/sub>CHOHCHO). (Hint: as a substituent, the OH group is named <em class=\"emphasis\">hydroxy<\/em>.)<\/p>\r\n\r\n<\/div>\r\n&nbsp;<\/li>\r\n<\/ol>\r\n[reveal-answer q=\"689110\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"689110\"]\r\n\r\n1.<img class=\"aligncenter\" style=\"font-size: 0.9em\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150808\/bc2b0cb1f17c1603e740de01133323da.jpg\" alt=\"image\" \/>\r\n\r\n3-bromobenzaldehyde\r\n\r\n2.\u00a02,3-dihydroxypropanal\r\n\r\n<span style=\"font-size: 1rem;text-align: initial\">\u00a0[\/hidden-answer]<\/span>\r\n\r\n<\/div>\r\n<\/div>\r\n<div class=\"textbox key-takeaways\">\r\n<h3>Key Takeaways<\/h3>\r\n<div id=\"gob-ch14_s09_s01_n09\" class=\"key_takeaways editable block\">\r\n<ul id=\"gob-ch14_s09_s01_l12\" class=\"itemizedlist\">\r\n \t<li>The common names of aldehydes are taken from the names of the corresponding carboxylic acids: formaldehyde, acetaldehyde, and so on.<\/li>\r\n \t<li>The common names of ketones, like those of ethers, consist of the names of the groups attached to the carbonyl group, followed by the word <em class=\"emphasis\">ketone<\/em>.<\/li>\r\n \t<li>Stem names of aldehydes and ketones are derived from those of the parent alkanes, using an -<em class=\"emphasis\">al<\/em> ending for an aldehydes and an -<em class=\"emphasis\">one<\/em> ending for a ketone.<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>\r\n<div class=\"textbox exercises\">\r\n<h3>Exercises<\/h3>\r\n<div id=\"gob-ch14_s09_qs05\" class=\"qandaset block\">\r\n<ol id=\"gob-ch14_s09_qs05_qd01\" class=\"qandadiv\">\r\n \t<li id=\"gob-ch14_s09_qs05_qd01_qa01\" class=\"qandaentry\">\r\n<div class=\"question\">\r\n<p id=\"gob-ch14_s09_qs05_p01\" class=\"para\">Name each compound.<\/p>\r\n\r\n<ol id=\"gob-ch14_s09_qs05_l01\" class=\"orderedlist\">\r\n \t<li>\r\n<div class=\"informalfigure large\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150811\/bd64e64065c94085add603c7fc3ab2ba.jpg\" alt=\"image\" \/><\/div><\/li>\r\n \t<li>\r\n<div class=\"informalfigure large\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150814\/0ac2f53674f4c92ae9a8eef18176655e.jpg\" alt=\"image\" \/><\/div><\/li>\r\n \t<li>\r\n<div class=\"informalfigure large\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150817\/6ed52ed5a4a54e078ebba5cfde29c762.jpg\" alt=\"image\" \/><\/div><\/li>\r\n \t<li>\r\n<div class=\"informalfigure large\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150820\/03b4397e4abb45d0c9356467eb29dd69.jpg\" alt=\"image\" \/><\/div><\/li>\r\n<\/ol>\r\n<\/div><\/li>\r\n \t<li id=\"gob-ch14_s09_qs05_qd01_qa02\" class=\"qandaentry\">\r\n<div class=\"question\">\r\n<p id=\"gob-ch14_s09_qs05_p02\" class=\"para\">Name each compound.<\/p>\r\n\r\n<ol id=\"gob-ch14_s09_qs05_l03\" class=\"orderedlist\">\r\n \t<li>\r\n<div class=\"informalfigure large\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150824\/ed36a6841de3477f8b5e07456373b3b0.jpg\" alt=\"image\" \/><\/div><\/li>\r\n \t<li>CH<sub class=\"subscript\">3<\/sub>CH<sub class=\"subscript\">2<\/sub>CH<sub class=\"subscript\">2<\/sub>CH<sub class=\"subscript\">2<\/sub>CH<sub class=\"subscript\">2<\/sub>CHO<\/li>\r\n \t<li>\r\n<div class=\"informalfigure large\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150826\/5064ff38d05009c294b307515447db91.jpg\" alt=\"image\" \/><\/div><\/li>\r\n \t<li>\r\n<div class=\"informalfigure large\"><img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150829\/73bcecc59a7ad954d081f51adf180268.jpg\" alt=\"image\" \/><\/div><\/li>\r\n<\/ol>\r\n<\/div><\/li>\r\n \t<li id=\"gob-ch14_s09_qs05_qd01_qa03\" class=\"qandaentry\">\r\n<div class=\"question\">\r\n<p id=\"gob-ch14_s09_qs05_p03\" class=\"para\">Draw the structure for each compound.<\/p>\r\n\r\n<ol id=\"gob-ch14_s09_qs05_l05\" class=\"orderedlist\">\r\n \t<li>butanal<\/li>\r\n \t<li>2-hexanone<\/li>\r\n \t<li><em class=\"emphasis\">p<\/em>-nitrobenzaldehyde<\/li>\r\n<\/ol>\r\n<\/div><\/li>\r\n \t<li id=\"gob-ch14_s09_qs05_qd01_qa04\" class=\"qandaentry\">\r\n<div class=\"question\">\r\n<p id=\"gob-ch14_s09_qs05_p04\" class=\"para\">Draw the structure for each compound.<\/p>\r\n\r\n<ol id=\"gob-ch14_s09_qs05_l07\" class=\"orderedlist\">\r\n \t<li>5-ethyloctanal<\/li>\r\n \t<li>2-chloropropanal<\/li>\r\n \t<li>2-hydroxy-3-pentanone<\/li>\r\n<\/ol>\r\n<\/div>\r\n&nbsp;<\/li>\r\n<\/ol>\r\n[reveal-answer q=\"889036\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"889036\"]1. a. propanal or propionaldehyde\r\n\r\nb. butanal or butyraldehyde\r\n\r\nc. 3-pentanone or diethyl ketone\r\n\r\nd. benzaldehyde\r\n\r\n3. a. CH<sub>3<\/sub>CH<sub>2<\/sub>CH<sub>2<\/sub>CHO\r\n\r\nb.<img class=\"aligncenter\" style=\"font-size: 0.9em\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150832\/0ad48e399f118d7177538d85bf71369b.jpg\" alt=\"image\" \/>\r\n\r\n<span style=\"font-size: 1rem;text-align: initial\">c.\u00a0<\/span><img class=\"aligncenter\" style=\"font-size: 0.9em\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150834\/344612c37ec764a0368a9c285949059f.jpg\" alt=\"image\" \/><span style=\"font-size: 1rem;text-align: initial\">\u00a0[\/hidden-answer]<\/span>\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>","rendered":"<div id=\"navbar-top\" class=\"navbar\"><\/div>\n<div id=\"book-content\">\n<div id=\"gob-ch14_s09\" class=\"section\" xml:lang=\"en\">\n<div id=\"gob-ch14_s09_n01\" class=\"learning_objectives editable block\">\n<div class=\"textbox learning-objectives\">\n<h3 class=\"title\">Learning Objectives<\/h3>\n<ol id=\"gob-ch14_s09_l01\" class=\"orderedlist\">\n<li>Identify the general structure for an aldehyde and a ketone.<\/li>\n<li>Use common names to name aldehydes and ketones.<\/li>\n<li>Use the IUPAC system to name aldehydes and ketones.<\/li>\n<\/ol>\n<\/div>\n<p><span style=\"font-size: 1rem;text-align: initial\">The next functional group we consider, the <\/span><span class=\"margin_term\" style=\"font-size: 1rem;text-align: initial\"><span class=\"glossterm\">carbonyl group<\/span><\/span><span style=\"font-size: 1rem;text-align: initial\">, has a carbon-to-oxygen double bond.<\/span><\/p>\n<\/div>\n<div class=\"informalfigure large block\"><img decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150709\/c99afd71e60c6d951c0a506e18d676e2.jpg\" alt=\"image\" \/><\/div>\n<p id=\"gob-ch14_s09_p02\" class=\"para editable block\">Carbonyl groups define two related families of organic compounds: the aldehydes and the ketones.\u00a0 The carbonyl group is also found in Carboxylic acids, esters, and amides, which will be discussed in other sections.<\/p>\n<div id=\"gob-ch14_s09_n02\" class=\"callout editable block\">\n<div class=\"textbox\">\n<h3 class=\"title\">Note<\/h3>\n<p id=\"gob-ch14_s09_p03\" class=\"para\">The carbonyl group is ubiquitous in biological compounds. It is found in carbohydrates, fats, proteins, nucleic acids, hormones, and vitamins\u2014organic compounds critical to living systems.<\/p>\n<\/div>\n<\/div>\n<p id=\"gob-ch14_s09_p04\" class=\"para editable block\">In a <span class=\"margin_term\"><span class=\"glossterm\">ketone<\/span><\/span>, two carbon groups are attached to the carbonyl carbon atom. The following general formulas, in which R represents an alkyl group and Ar stands for an aryl group, represent ketones.<\/p>\n<div class=\"informalfigure large block\"><img decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150712\/3a2c2bc1cdf2ee3389d8e891bd649eb1.jpg\" alt=\"image\" \/><\/div>\n<p id=\"gob-ch14_s09_p05\" class=\"para editable block\">In an <span class=\"margin_term\"><span class=\"glossterm\">aldehyde<\/span><\/span>, at least one of the attached groups must be a hydrogen atom. The following compounds are aldehydes:<\/p>\n<div class=\"informalfigure large block\"><img decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150714\/aea4705b99aaa721f6011c448cb1e67d.jpg\" alt=\"image\" \/><\/div>\n<p id=\"gob-ch14_s09_p06\" class=\"para editable block\">In condensed formulas, we use CHO to identify an aldehyde rather than COH, which might be confused with an alcohol. This follows the general rule that in condensed structural formulas H comes after the atom it is attached to (usually C, N, or O).<\/p>\n<div class=\"informalfigure large block\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150717\/4b27089fc7763d264d34c0dcd4c13dd6.jpg\" alt=\"image\" \/><\/div>\n<p id=\"gob-ch14_s09_p07\" class=\"para editable block\">The carbon-to-oxygen double bond is not shown but understood to be present.<\/p>\n<p id=\"gob-ch14_s09_p08\" class=\"para editable block\">Because they contain the same functional group, aldehydes and ketones share many common properties, but they still differ enough to warrant their classification into two families.<\/p>\n<div id=\"gob-ch14_s09_s01\" class=\"section\">\n<h2 class=\"title editable block\">Naming Aldehydes and Ketones<\/h2>\n<p id=\"gob-ch14_s09_s01_p01\" class=\"para editable block\">Both common and International Union of Pure and Applied Chemistry (IUPAC) names are frequently used for aldehydes and ketones, with common names predominating for the lower homologs. The common names of aldehydes are taken from the names of the acids into which the aldehydes can be converted by oxidation. (For more information about carboxylic acids, see <a class=\"xref\" href=\"..\/suny-orgbiochemistry\/chapter\/introduction-15\">Chapter 15 &#8220;Organic Acids and Bases and Some of Their Derivatives&#8221;<\/a>, <a class=\"xref\" href=\"gob-ch15_s02#gob-ch15_s02\">Section 15.2 &#8220;Carboxylic Acids: Structures and Names&#8221;<\/a> through <a class=\"xref\" href=\"gob-ch15_s04#gob-ch15_s04\">Section 15.4 &#8220;Physical Properties of Carboxylic Acids&#8221;<\/a>.)<\/p>\n<div class=\"informalfigure large block\"><img decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150720\/a4342afac9b9fa33eef54dbef9827067.jpg\" alt=\"image\" \/><\/div>\n<div id=\"gob-ch14_s09_s01_n01\" class=\"callout editable block\">\n<div class=\"textbox\">\n<h3 class=\"title\">Note<\/h3>\n<p id=\"gob-ch14_s09_s01_p02\" class=\"para\">The stems for the common names of the first four aldehydes are as follows:<\/p>\n<ul id=\"gob-ch14_s09_s01_l01\" class=\"itemizedlist\">\n<li>1 carbon atom: <em class=\"emphasis\">form<\/em>&#8211;<\/li>\n<li>2 carbon atoms: <em class=\"emphasis\">acet<\/em>&#8211;<\/li>\n<li>3 carbon atoms: <em class=\"emphasis\">propion<\/em>&#8211;<\/li>\n<li>4 carbon atoms: <em class=\"emphasis\">butyr<\/em>&#8211;<\/li>\n<\/ul>\n<\/div>\n<\/div>\n<p id=\"gob-ch14_s09_s01_p03\" class=\"para editable block\">Because the carbonyl group in a ketone must be attached to two carbon groups, the simplest ketone has three carbon atoms. It is widely known as <em class=\"emphasis\">acetone<\/em>, a unique name unrelated to other common names for ketones.<\/p>\n<div class=\"informalfigure large block\"><img decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150723\/e2edc94ebd7f46df06b99e74ed3bd654.jpg\" alt=\"image\" \/><\/div>\n<p id=\"gob-ch14_s09_s01_p04\" class=\"para editable block\">Generally, the common names of ketones consist of the names of the groups attached to the carbonyl group, followed by the word <em class=\"emphasis\">ketone<\/em>. (Note the similarity to the naming of ethers.) Another name for acetone, then, is <em class=\"emphasis\">dimethyl ketone.<\/em> The ketone with four carbon atoms is ethyl methyl ketone.<\/p>\n<div class=\"informalfigure large block\"><img decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150726\/b6b55f1bdf24ab08ba511096637efd9f.jpg\" alt=\"image\" \/><\/div>\n<div id=\"gob-ch14_s09_s01_n02\" class=\"exercises editable block\">\n<h3 class=\"title\">Example 6<\/h3>\n<p id=\"gob-ch14_s09_s01_p05\" class=\"para\">Classify each compound as an aldehyde or a ketone. Give the common name for each ketone.<\/p>\n<ol id=\"gob-ch14_s09_s01_l02\" class=\"orderedlist\">\n<li>\n<div class=\"informalfigure large\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150729\/936d06564f4a5e15df10dc4018a6d4b8.jpg\" alt=\"image\" \/><\/div>\n<\/li>\n<li>\n<div class=\"informalfigure large\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150732\/5a3e5cf375b47a091fd1db2c837b30f2.jpg\" alt=\"image\" \/><\/div>\n<\/li>\n<li>\n<div class=\"informalfigure large\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150735\/d3d0cb767cda253ed0e3a6d63b3b1219.jpg\" alt=\"image\" \/><\/div>\n<\/li>\n<\/ol>\n<p class=\"simpara\">Solution<\/p>\n<ol id=\"gob-ch14_s09_s01_l03\" class=\"orderedlist\">\n<li>This compound has the carbonyl group on an end carbon atom, so it is an aldehyde.<\/li>\n<li>This compound has the carbonyl group on an interior carbon atom, so it is a ketone. Both alkyl groups are propyl groups. The name is therefore dipropyl ketone.<\/li>\n<li>This compound has the carbonyl group between two alkyl groups, so it is a ketone. One alkyl group has three carbon atoms and is attached by the middle carbon atom; it is an isopropyl group. A group with one carbon atom is a methyl group. The name is therefore isopropyl methyl ketone.<\/li>\n<\/ol>\n<\/div>\n<div id=\"gob-ch14_s09_qs01\" class=\"qandaset block\">\n<div class=\"textbox shaded\">\n<h3 class=\"title\">Skill-Building Exercise<\/h3>\n<p class=\"title\">Classify each compound as an aldehyde or a ketone. Give the common name for each ketone.<\/p>\n<ol id=\"gob-ch14_s09_qs01_qd01\" class=\"qandadiv\">\n<li id=\"gob-ch14_s09_qs01_qd01_qa01\" class=\"qandaentry\">\n<div class=\"question\">\n<div class=\"informalfigure large\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150737\/d564bb3d2391b00c9de1b892938ffa84.jpg\" alt=\"image\" \/><\/div>\n<\/div>\n<\/li>\n<li id=\"gob-ch14_s09_qs01_qd01_qa02\" class=\"qandaentry\">\n<div class=\"question\">\n<div class=\"informalfigure large\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150740\/5a5a2ed8e7caf01167dad9765e57218f.jpg\" alt=\"image\" \/><\/div>\n<\/div>\n<\/li>\n<li id=\"gob-ch14_s09_qs01_qd01_qa03\" class=\"qandaentry\">\n<div class=\"question\">\n<div class=\"informalfigure large\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150743\/60e1bd998fac7ad65662551494071e4b.jpg\" alt=\"image\" \/><\/div>\n<\/div>\n<\/li>\n<\/ol>\n<\/div>\n<p><span style=\"font-size: 1rem;text-align: initial\">Here are some simple IUPAC rules for naming aldehydes and ketones:<\/span><\/p>\n<\/div>\n<ol id=\"gob-ch14_s09_s01_l05\" class=\"orderedlist editable block\">\n<li>The stem names of aldehydes and ketones are derived from those of the parent alkanes, defined by the longest continuous chain (LCC) of carbon atoms that contains the functional group.<\/li>\n<li>For an aldehyde, drop the &#8211;<em class=\"emphasis\">e<\/em> from the alkane name and add the ending &#8211;<em class=\"emphasis\">al<\/em>. Methanal is the IUPAC name for formaldehyde, and ethanal is the name for acetaldehyde.<\/li>\n<li>For a ketone, drop the &#8211;<em class=\"emphasis\">e<\/em> from the alkane name and add the ending &#8211;<em class=\"emphasis\">one<\/em>. Propanone is the IUPAC name for acetone, and butanone is the name for ethyl methyl ketone.<\/li>\n<li>To indicate the position of a substituent on an aldehyde, the carbonyl carbon atom is always considered to be C1; it is unnecessary to designate this group by number.<\/li>\n<li>To indicate the position of a substituent on a ketone, number the chain in the manner that gives the carbonyl carbon atom the lowest possible number. In cyclic ketones, it is understood that the carbonyl carbon atom is C1.<\/li>\n<\/ol>\n<div id=\"gob-ch14_s09_s01_n04\" class=\"exercises editable block\">\n<h3 class=\"title\">Example 7<\/h3>\n<p id=\"gob-ch14_s09_s01_p11\" class=\"para\">Give the IUPAC name for each compound.<\/p>\n<ol id=\"gob-ch14_s09_s01_l06\" class=\"orderedlist\">\n<li>\n<div class=\"informalfigure large\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150746\/f8433f746ceda879e02ec31aa113bfe8.jpg\" alt=\"image\" \/><\/div>\n<\/li>\n<li>\n<div class=\"informalfigure large\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150749\/c3c5aa121cd09ded3ad9cecd905903a6.jpg\" alt=\"image\" \/><\/div>\n<\/li>\n<li>\n<div class=\"informalfigure large\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150752\/7552c41ec3ff1d2181167793498bfffa.jpg\" alt=\"image\" \/><\/div>\n<\/li>\n<\/ol>\n<p class=\"simpara\">Solution<\/p>\n<ol id=\"gob-ch14_s09_s01_l07\" class=\"orderedlist\">\n<li>There are five carbon atoms in the LCC. The methyl group (CH<sub class=\"subscript\">3<\/sub>) is a substituent on the second carbon atom of the chain; the aldehyde carbon atom is always C1. The name is derived from pentane. Dropping the &#8211;<em class=\"emphasis\">e<\/em> and adding the ending &#8211;<em class=\"emphasis\">al<\/em> gives pentanal. The methyl group on the second carbon atom makes the name 2-methylpentanal.<\/li>\n<li>There are five carbon atoms in the LCC. The carbonyl carbon atom is C3, and there are methyl groups on C2 and C4. The IUPAC name is 2,4-dimethyl-3-pentanone.<\/li>\n<li>There are six carbon atoms in the ring. The compound is cyclohexanone. No number is needed to indicate the position of the carbonyl group because all six carbon atoms are equivalent.<\/li>\n<\/ol>\n<\/div>\n<div id=\"gob-ch14_s09_qs02\" class=\"qandaset block\">\n<div class=\"textbox shaded\">\n<h3 class=\"title\">Skill-Building Exercise<\/h3>\n<p class=\"title\">Give the IUPAC name for each compound.<\/p>\n<ol id=\"gob-ch14_s09_qs02_qd01\" class=\"qandadiv\">\n<li id=\"gob-ch14_s09_qs02_qd01_qa01\" class=\"qandaentry\">\n<div class=\"question\">\n<div class=\"informalfigure large\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150755\/9d30dbb9670be9cabfbfd913d977def4.jpg\" alt=\"image\" \/><\/div>\n<\/div>\n<\/li>\n<li id=\"gob-ch14_s09_qs02_qd01_qa02\" class=\"qandaentry\">\n<div class=\"question\">\n<div class=\"informalfigure large\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150758\/85e8f3cbaefd3cf6c6bce9bacc4ff59a.jpg\" alt=\"image\" \/><\/div>\n<\/div>\n<\/li>\n<li id=\"gob-ch14_s09_qs02_qd01_qa03\" class=\"qandaentry\">\n<div class=\"question\">\n<div class=\"informalfigure large\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150800\/27452d4f63aa775eeb5f1df9964f74ba.jpg\" alt=\"image\" \/><\/div>\n<\/div>\n<\/li>\n<\/ol>\n<\/div>\n<\/div>\n<div id=\"gob-ch14_s09_s01_n06\" class=\"exercises editable block\">\n<h3 class=\"title\">Example 8<\/h3>\n<p id=\"gob-ch14_s09_s01_p16\" class=\"para\">Draw the structure for each compound.<\/p>\n<ol id=\"gob-ch14_s09_s01_l09\" class=\"orderedlist\">\n<li>7-chlorooctanal<\/li>\n<li>4-methyl\u20133-hexanone<\/li>\n<\/ol>\n<p class=\"simpara\">Solution<\/p>\n<ol id=\"gob-ch14_s09_s01_l10\" class=\"orderedlist\">\n<li>\n<p class=\"para\">The <em class=\"emphasis\">octan<\/em>&#8211; part of the name tells us that the LCC has eight carbon atoms. There is a chlorine (Cl) atom on the seventh carbon atom; numbering from the carbonyl group and counting the carbonyl carbon atom as C1, we place the Cl atom on the seventh carbon atom.<\/p>\n<div class=\"informalfigure large\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150803\/4899969d52c9566dc6cbb8f70dd6daf5.jpg\" alt=\"image\" \/><\/div>\n<\/li>\n<li>\n<p class=\"para\">The <em class=\"emphasis\">hexan<\/em>&#8211; part of the name tells us that the LCC has six carbon atoms. The 3 means that the carbonyl carbon atom is C3 in this chain, and the 4 tells us that there is a methyl (CH<sub class=\"subscript\">3<\/sub>) group at C4:<\/p>\n<div class=\"informalfigure large\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150806\/e0e0b6646c77c00b6d0ed135bab4ee70.jpg\" alt=\"image\" \/><\/div>\n<\/li>\n<\/ol>\n<\/div>\n<div id=\"gob-ch14_s09_qs03\" class=\"qandaset block\">\n<div class=\"textbox shaded\">\n<h3 class=\"title\">Skill-Building Exercise<\/h3>\n<p class=\"title\">Draw the structure for each compound.<\/p>\n<ol id=\"gob-ch14_s09_qs03_qd01\" class=\"qandadiv\">\n<li id=\"gob-ch14_s09_qs03_qd01_qa01\" class=\"qandaentry\">\n<div class=\"question\">\n<p id=\"gob-ch14_s09_qs03_p02\" class=\"para\">5-bromo-3-iodoheptanal<\/p>\n<\/div>\n<\/li>\n<li id=\"gob-ch14_s09_qs03_qd01_qa02\" class=\"qandaentry\">\n<div class=\"question\">\n<p id=\"gob-ch14_s09_qs03_p03\" class=\"para\">5-bromo-4-ethyl-2-heptanone<\/p>\n<\/div>\n<\/li>\n<\/ol>\n<\/div>\n<\/div>\n<div id=\"gob-ch14_s09_qs04\" class=\"qandaset block\">\n<div class=\"textbox exercises\">\n<div id=\"gob-ch14_s09_qs04\" class=\"qandaset block\">\n<h3 class=\"title\">Concept Review Exercises<\/h3>\n<ol id=\"gob-ch14_s09_qs04_qd01\" class=\"qandadiv\">\n<li id=\"gob-ch14_s09_qs04_qd01_qa01\" class=\"qandaentry\">\n<div class=\"question\">\n<p id=\"gob-ch14_s09_qs04_p01\" class=\"para\">Give the structure and IUPAC name for the compound that has the common name <em class=\"emphasis\">m<\/em>-bromobenzaldehyde (see <a class=\"xref\" href=\"gob-ch14_s10#gob-ch14_s10_s02_f01\">Figure 14.6 &#8220;Some Interesting Aldehydes&#8221;<\/a> for the structure of benzaldehyde).<\/p>\n<\/div>\n<\/li>\n<li id=\"gob-ch14_s09_qs04_qd01_qa02\" class=\"qandaentry\">\n<div class=\"question\">\n<p id=\"gob-ch14_s09_qs04_p03\" class=\"para\">Give the IUPAC name for glyceraldehyde, (HOCH<sub class=\"subscript\">2<\/sub>CHOHCHO). (Hint: as a substituent, the OH group is named <em class=\"emphasis\">hydroxy<\/em>.)<\/p>\n<\/div>\n<p>&nbsp;<\/li>\n<\/ol>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q689110\">Show Answer<\/span><\/p>\n<div id=\"q689110\" class=\"hidden-answer\" style=\"display: none\">\n<p>1.<img decoding=\"async\" class=\"aligncenter\" style=\"font-size: 0.9em\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150808\/bc2b0cb1f17c1603e740de01133323da.jpg\" alt=\"image\" \/><\/p>\n<p>3-bromobenzaldehyde<\/p>\n<p>2.\u00a02,3-dihydroxypropanal<\/p>\n<p><span style=\"font-size: 1rem;text-align: initial\">\u00a0<\/div>\n<\/div>\n<p><\/span><\/p>\n<\/div>\n<\/div>\n<div class=\"textbox key-takeaways\">\n<h3>Key Takeaways<\/h3>\n<div id=\"gob-ch14_s09_s01_n09\" class=\"key_takeaways editable block\">\n<ul id=\"gob-ch14_s09_s01_l12\" class=\"itemizedlist\">\n<li>The common names of aldehydes are taken from the names of the corresponding carboxylic acids: formaldehyde, acetaldehyde, and so on.<\/li>\n<li>The common names of ketones, like those of ethers, consist of the names of the groups attached to the carbonyl group, followed by the word <em class=\"emphasis\">ketone<\/em>.<\/li>\n<li>Stem names of aldehydes and ketones are derived from those of the parent alkanes, using an &#8211;<em class=\"emphasis\">al<\/em> ending for an aldehydes and an &#8211;<em class=\"emphasis\">one<\/em> ending for a ketone.<\/li>\n<\/ul>\n<\/div>\n<\/div>\n<div class=\"textbox exercises\">\n<h3>Exercises<\/h3>\n<div id=\"gob-ch14_s09_qs05\" class=\"qandaset block\">\n<ol id=\"gob-ch14_s09_qs05_qd01\" class=\"qandadiv\">\n<li id=\"gob-ch14_s09_qs05_qd01_qa01\" class=\"qandaentry\">\n<div class=\"question\">\n<p id=\"gob-ch14_s09_qs05_p01\" class=\"para\">Name each compound.<\/p>\n<ol id=\"gob-ch14_s09_qs05_l01\" class=\"orderedlist\">\n<li>\n<div class=\"informalfigure large\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150811\/bd64e64065c94085add603c7fc3ab2ba.jpg\" alt=\"image\" \/><\/div>\n<\/li>\n<li>\n<div class=\"informalfigure large\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150814\/0ac2f53674f4c92ae9a8eef18176655e.jpg\" alt=\"image\" \/><\/div>\n<\/li>\n<li>\n<div class=\"informalfigure large\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150817\/6ed52ed5a4a54e078ebba5cfde29c762.jpg\" alt=\"image\" \/><\/div>\n<\/li>\n<li>\n<div class=\"informalfigure large\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150820\/03b4397e4abb45d0c9356467eb29dd69.jpg\" alt=\"image\" \/><\/div>\n<\/li>\n<\/ol>\n<\/div>\n<\/li>\n<li id=\"gob-ch14_s09_qs05_qd01_qa02\" class=\"qandaentry\">\n<div class=\"question\">\n<p id=\"gob-ch14_s09_qs05_p02\" class=\"para\">Name each compound.<\/p>\n<ol id=\"gob-ch14_s09_qs05_l03\" class=\"orderedlist\">\n<li>\n<div class=\"informalfigure large\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150824\/ed36a6841de3477f8b5e07456373b3b0.jpg\" alt=\"image\" \/><\/div>\n<\/li>\n<li>CH<sub class=\"subscript\">3<\/sub>CH<sub class=\"subscript\">2<\/sub>CH<sub class=\"subscript\">2<\/sub>CH<sub class=\"subscript\">2<\/sub>CH<sub class=\"subscript\">2<\/sub>CHO<\/li>\n<li>\n<div class=\"informalfigure large\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150826\/5064ff38d05009c294b307515447db91.jpg\" alt=\"image\" \/><\/div>\n<\/li>\n<li>\n<div class=\"informalfigure large\"><img decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150829\/73bcecc59a7ad954d081f51adf180268.jpg\" alt=\"image\" \/><\/div>\n<\/li>\n<\/ol>\n<\/div>\n<\/li>\n<li id=\"gob-ch14_s09_qs05_qd01_qa03\" class=\"qandaentry\">\n<div class=\"question\">\n<p id=\"gob-ch14_s09_qs05_p03\" class=\"para\">Draw the structure for each compound.<\/p>\n<ol id=\"gob-ch14_s09_qs05_l05\" class=\"orderedlist\">\n<li>butanal<\/li>\n<li>2-hexanone<\/li>\n<li><em class=\"emphasis\">p<\/em>-nitrobenzaldehyde<\/li>\n<\/ol>\n<\/div>\n<\/li>\n<li id=\"gob-ch14_s09_qs05_qd01_qa04\" class=\"qandaentry\">\n<div class=\"question\">\n<p id=\"gob-ch14_s09_qs05_p04\" class=\"para\">Draw the structure for each compound.<\/p>\n<ol id=\"gob-ch14_s09_qs05_l07\" class=\"orderedlist\">\n<li>5-ethyloctanal<\/li>\n<li>2-chloropropanal<\/li>\n<li>2-hydroxy-3-pentanone<\/li>\n<\/ol>\n<\/div>\n<p>&nbsp;<\/li>\n<\/ol>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q889036\">Show Answer<\/span><\/p>\n<div id=\"q889036\" class=\"hidden-answer\" style=\"display: none\">1. a. propanal or propionaldehyde<\/p>\n<p>b. butanal or butyraldehyde<\/p>\n<p>c. 3-pentanone or diethyl ketone<\/p>\n<p>d. benzaldehyde<\/p>\n<p>3. a. CH<sub>3<\/sub>CH<sub>2<\/sub>CH<sub>2<\/sub>CHO<\/p>\n<p>b.<img decoding=\"async\" class=\"aligncenter\" style=\"font-size: 0.9em\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150832\/0ad48e399f118d7177538d85bf71369b.jpg\" alt=\"image\" \/><\/p>\n<p><span style=\"font-size: 1rem;text-align: initial\">c.\u00a0<\/span><img decoding=\"async\" class=\"aligncenter\" style=\"font-size: 0.9em\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21150834\/344612c37ec764a0368a9c285949059f.jpg\" alt=\"image\" \/><span style=\"font-size: 1rem;text-align: initial\">\u00a0<\/div>\n<\/div>\n<p><\/span><\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n\n\t\t\t <section class=\"citations-section\" role=\"contentinfo\">\n\t\t\t <h3>Candela Citations<\/h3>\n\t\t\t\t\t <div>\n\t\t\t\t\t\t <div id=\"citation-list-1447\">\n\t\t\t\t\t\t\t <div class=\"licensing\"><div class=\"license-attribution-dropdown-subheading\">CC licensed content, Shared previously<\/div><ul class=\"citation-list\"><li>The Basics of General, Organic, and Biological Chemistry v. 1.0. <strong>Provided by<\/strong>: Saylor Academy. <strong>Located at<\/strong>: <a target=\"_blank\" href=\"https:\/\/saylordotorg.github.io\/text_the-basics-of-general-organic-and-biological-chemistry\/\">https:\/\/saylordotorg.github.io\/text_the-basics-of-general-organic-and-biological-chemistry\/<\/a>. <strong>License<\/strong>: <em><a target=\"_blank\" rel=\"license\" href=\"https:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/\">CC BY-NC: Attribution-NonCommercial<\/a><\/em>. <strong>License Terms<\/strong>: This text was adapted by Saylor Academy under a Creative Commons Attribution-NonCommercial-ShareAlike 3.0 License without attribution as requested by the work&#039;s original creator or licensor.<\/li><\/ul><\/div>\n\t\t\t\t\t\t <\/div>\n\t\t\t\t\t <\/div>\n\t\t\t <\/section>","protected":false},"author":53384,"menu_order":10,"template":"","meta":{"_candela_citation":"[{\"type\":\"cc\",\"description\":\"The Basics of General, Organic, and Biological Chemistry v. 1.0\",\"author\":\"\",\"organization\":\"Saylor Academy\",\"url\":\"https:\/\/saylordotorg.github.io\/text_the-basics-of-general-organic-and-biological-chemistry\/\",\"project\":\"\",\"license\":\"cc-by-nc\",\"license_terms\":\"This text was adapted by Saylor Academy under a Creative Commons Attribution-NonCommercial-ShareAlike 3.0 License without attribution as requested by the work\\'s original creator or licensor.\"}]","CANDELA_OUTCOMES_GUID":"","pb_show_title":"on","pb_short_title":"","pb_subtitle":"","pb_authors":[],"pb_section_license":""},"chapter-type":[],"contributor":[],"license":[],"class_list":["post-1447","chapter","type-chapter","status-publish","hentry"],"part":1285,"_links":{"self":[{"href":"https:\/\/courses.lumenlearning.com\/suny-monroecc-orgbiochemistry\/wp-json\/pressbooks\/v2\/chapters\/1447","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/courses.lumenlearning.com\/suny-monroecc-orgbiochemistry\/wp-json\/pressbooks\/v2\/chapters"}],"about":[{"href":"https:\/\/courses.lumenlearning.com\/suny-monroecc-orgbiochemistry\/wp-json\/wp\/v2\/types\/chapter"}],"author":[{"embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-monroecc-orgbiochemistry\/wp-json\/wp\/v2\/users\/53384"}],"version-history":[{"count":12,"href":"https:\/\/courses.lumenlearning.com\/suny-monroecc-orgbiochemistry\/wp-json\/pressbooks\/v2\/chapters\/1447\/revisions"}],"predecessor-version":[{"id":3520,"href":"https:\/\/courses.lumenlearning.com\/suny-monroecc-orgbiochemistry\/wp-json\/pressbooks\/v2\/chapters\/1447\/revisions\/3520"}],"part":[{"href":"https:\/\/courses.lumenlearning.com\/suny-monroecc-orgbiochemistry\/wp-json\/pressbooks\/v2\/parts\/1285"}],"metadata":[{"href":"https:\/\/courses.lumenlearning.com\/suny-monroecc-orgbiochemistry\/wp-json\/pressbooks\/v2\/chapters\/1447\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/courses.lumenlearning.com\/suny-monroecc-orgbiochemistry\/wp-json\/wp\/v2\/media?parent=1447"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-monroecc-orgbiochemistry\/wp-json\/pressbooks\/v2\/chapter-type?post=1447"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-monroecc-orgbiochemistry\/wp-json\/wp\/v2\/contributor?post=1447"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-monroecc-orgbiochemistry\/wp-json\/wp\/v2\/license?post=1447"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}