Dolbier HW Solutions 426

Dolbier HW Solutions 426 - H 2 O, acetic acid H 2 SO 4 ,...

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19.22 ( a ) Carboxylic acids are converted to ethyl esters when they are allowed to stand in ethanol in the presence of an acid catalyst. ( b ) Lithium aluminum hydride, LiAlH 4 , reduces carboxylic acids to primary alcohols. When LiAlD 4 is used, deuterium is transferred to the carbonyl carbon. Notice that deuterium is bonded only to carbon. The hydroxyl proton is derived from water, not from the reducing agent. ( c ) In the presence of a catalytic amount of phosphorus, bromine reacts with carboxylic acids to yield the corresponding a -bromo derivative. ( d ) Alkyl f uorides are not readily converted to Grignard reagents, and so it is the bromine sub- stituent that is attacked by magnesium. ( e ) Cyano substituents are hydrolyzed to carboxyl groups in the presence of acid catalysts.
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Unformatted text preview: H 2 O, acetic acid H 2 SO 4 , heat CH 2 CO 2 H Cl m-Chlorophenylacetic acid (61%) CH 2 CN Cl m-Chlorobenzyl cyanide CF 3 MgBr Mg diethyl ether CF 3 Br m-Bromo(trifluoromethyl)-benzene 1. CO 2 2. H 3 O 1 CF 3 CO 2 H m-(Trifluoromethyl)-benzoic acid Cyclohexanecarboxylic acid CO 2 H Br 2 P 1-Bromocyclohexanecarboxylic acid (96%) CO 2 H Br Cyclopropanecarboxylic acid COH O 1-Cyclopropyl-1,1-dideuteriomethanol (75%) COH D D 1. LiAlD 4 , diethyl ether 2. H 2 O 1 Ethanol CH 3 CH 2 OH 1 Water H 2 O ( E )-2-Methyl-2-butenoic acid C H 3 C CH 3 CO 2 H H C Ethyl ( E )-2-methyl-2-butenoate (74 80%) O C H 3 C CH 3 COCH 2 CH 3 H C H 2 SO 4 520 CARBOXYLIC ACIDS __ __ __...
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This note was uploaded on 09/30/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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