Solutions_Manual_for_Organic_Chemistry_6th_Ed 474

Solutions_Manual_for_Organic_Chemistry_6th_Ed 474 - CHAPTER...

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Unformatted text preview: CHAPTER 20-CARBOXYLIC ACIDS 20-1 CH3 I (a) CH3CH2 CHCOOH (d) (g) ( Cl � COOH ) H '> t H OH (c) cf:�:� H (f) ( h) CI (k) N � COOH CH3 COOH (1) . N H2 I COOH HOOC � - (j) HOOC � COOH Cl � COOH o (I) 0(y 0 H 20-2 IUPAC name first; then common name. (a) 2-iodo-3-methylpentanoic acid; a-iodo-p-methylvaleric acid (b) (Z)-3,4-dimethylhex-3-enoic acid (c) 2,3-dinitrobenzoic acid; no common name (d) trans-cyclohexane-1,2-dicarboxylic acid; (trans-hexahydrophthalic acid) (e) 2-chlorobenzene-\ ,4-dicarbox ylic acid; 2-chloroterephthalic acid (f) 3 -mcthylhexanedioic acid; p-methyladipic acid 20-3 Listed in order of increasing acid strength (weakest acid first). (See Appendix 2 for a review of acidity.) Br CH3 - CCOOH (a) CH3CH2COOH < C H3 - CHCOOH < Br Br The greater the number of electron-withdrawing substituents, the greater the stabilization of the carboxylate ion. (b) CH3CHCH2CH 2COOH < C H3CH2CCH2 COOH < C H3CH2 CH2 CHCOOH I I I Br Br Br The closer the electron-withdrawing group, the greater the stabilization of the carboxylate ion. (c) CH3CH2 COOH < C H3-CHCOOH < C H3 - CHCOOH < C H3-CHCOOH N 02 o C �N The stronger the electron-withdrawing effect of the substituent, the greater the stabilization of the carboxylate ion. I I I I I I Va 4 69 ...
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