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ochem note - 1012T_mod05_1-36 7:34 Page 1 EQA MODULE 5...

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1 M O D U L E 5 ORGANIC CHEMISTRY: FUNCTIONAL GROUPS O2.1 Functional Groups O2.2 Oxidation–Reduction Reactions O2.3 Alkyl Halides O2.4 Alcohols and Ethers O2.5 Aldehydes and Ketones O2.6 Reactions at the Carbonyl Group O2.7 Carboxylic Acids and Carboxylate Ions O2.8 Esters O2.9 Amines, Alkaloids, and Amides O2.10 Grignard Reagents Chemistry in the World Around Us: The Chemistry of Garlic O2.1 FUNCTIONAL GROUPS Bromine reacts with 2-butene to form 2,3-dibromobutane. It also reacts with 3-methyl-2-pentene to form 2,3-dibromopentane. Instead of trying to memorize both equations, we can build a general rule that bromine re- acts with compounds that contain a C P C double bond to give the product expected from addition across the double bond. This approach to understanding the chemistry of organic compounds presumes that certain atoms or groups of atoms known as functional groups give these compounds their characteristic properties. CH 3 CH P C CH 3 CH 2 Br 2 CH 3 C A A Br HC A Br CH 3 CH 3 A CH 3 CH 2 CH 3 CH P CHCH 3 Br 2 CH 3 C A Br HC A Br HCH 3
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2 FUNCTIONAL GROUP CHEMISTRY Functional groups focus attention on the important aspects of the structure of a mol- ecule. We don’t have to worry about the differences between the structures of 1-butene and 2-methyl-2-hexene, for example, when the compounds react with hydrogen bromide. We can focus on the fact that both compounds are alkenes that add HBr across the C P C double bond in the direction predicted by Markovnikov’s rule, introduced in Section O1.8. Some common functional groups are given in Table O2.1. CH 3 C A CH 3 A CH 3 P CHCH 2 CH 2 CH HBr 3 CH 3 C A Br CH 2 CH 2 CH 2 CH 3 CH 2 CH P CH 2 CH 3 HBr CH 3 C A Br H CH 3 CH 2 Functional Group Name Example A O C O Alkane CH 3 CH 2 CH 3 (propane) A C P C Alkene CH 3 CH P CH 2 (propene) CH 3 C CH (propyne) C q C Alkyne q F, Cl, Br, or I Alkyl halide CH 3 Br (methyl bromide) O OH Alcohol CH 3 CH 2 OH (ethanol) O O O Ether CH 3 OCH 3 (dimethyl ether) O NH 2 Amine CH 3 NH 2 (methylamine) TABLE 02.1 Common Functional Groups The C P O group plays a particularly important role in organic chemistry. This group is called a carbonyl, and some of the functional groups based on a carbonyl are shown in Table O2.2. Functional Group Name Example O B O C O H Aldehyde CH 3 CHO (acetaldehyde) O B O C O Ketone CH 3 COCH 3 (acetone) O B O C O Cl Carboxylic acid CH 3 COCl (acetic acid) O B O C O OH Acyl chloride CH 3 CO H 2 (acetyl chloride) O B O C O O O Ester CH 3 CO 2 CH 3 (methyl acetate) O B O C O NH 2 Amide CH CO 3 NH 2 (acetamide) TABLE 02.2 Functional Groups That Contain a Carbonyl
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FUNCTIONAL GROUP CHEMISTRY 3 Exercise O2.1 Root beer hasn’t tasted the same since the use of sassafras oil as a food additive was out- lawed because sassafras oil is 80% safrole, which has been shown to cause cancer in rats and mice. Identify the functional groups in the structure of safrole.
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