Solutions_Manual_for_Organic_Chemistry_6th_Ed 488

Solutions_Manual_for_Organic_Chemistry_6th_Ed 488 - 20 2 0...

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Unformatted text preview: 20 2 0 (a) C H3 - C - OH II -8 (b) (e) (X � COOH (c) COOH 0 C lCH2 -C - OH II ( H-t O(f) 0 CH3-C - Ci II II ) 2 M g 2+ (a) ClCH2COO- < CH3COO- < PhO­ (c) PhCOO- Na+ 20-30 (a) (b) (c) 20-29 Weaker base listed first. (Weaker bases come from o 0- )2 (h) < }- C - O- Na+ 0 0 ( i) FCH2-C-0- Na+ stronger conjugate acids.) (X I 7" 1 � C OOH COOH + 2 NaOH CH3 (d) CH3 - CHCOOH + C H3CH2COO- Na+ CH3- CHCOO- Na+ Br Br (e) Na+ -0 COOH + COO- Na+ + HO o 031 0 OH CH3C-OCH2CH3 < < C H3CH2CH2 -C - OH � O� lowest b.p. (b.p. highest b.p. The ester cannot form hydrogen bonds and will be the lowest boiling. The alcohol can form hydrogen bonds. The carboxylic acid forms two hydrogen bonds and boils as the dimer, the highest boiling among these three compounds Listed in order of increasing acidity (weakest acid first): (a) ethanol < p henol < acetic acid EWG electron-withdrawing group (b) acetic acid < chloroacetic acid < p-toluenesulfonic acid Acidity increa�es. with: (c) benzoic acid < m-nitrobenzoic acid < o-nitrobenzoic acid 1. closer proxImIty of EWG (d) butyric acid < (3-bromobutyric acid < a-bromobutyric acid great number of EWG Cl Br increasing strength COOH (electronegativity) of EWG COOH < COOH < (e) 483 -Q- COOH (X � I COO- Na+ COO- Na+ no reaction 2- < }II .- -1 � 143°C) .. < }- I -1 � (n°C) 20-32 . ( l62°C) II n- 0= [yF } 2. = 3. ...
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