ORGANIC CHEMISTRY W/BIOLOGICAL TOPICS
6th Edition
ISBN: 9781260325294
Author: SMITH
Publisher: RENT MCG
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- Consider the data in the Table below to answer the following questions:
Acidities of Substituted Benzoic and Acetic Acids
pk,s at 25C
Y-CH COOH
Y
Y - CH₂COOH
meta
para
H
4.75
4.19
4.19
2.47
3.64
3.55
3.57
4.09
4.46
CN
OCH 3
A. Draw the structure of the strongest acid in the table above.
B. Explain why cyanoacetic acid and methoxyacetic acid are more acidic than their correspondingly
substituted benzoic acid counterparts.
Draw the curved arrow mechanism for this reaction starting with 2-propanol in sulfuric acid. Show all nonzero formal charges and all
nonbonded electrons in each step. Species not involved in a particular step do not need to be included in that step, and resonance forms
do not need to be shown. Note that the alcohol is in much higher concentration than H₂O in this reaction.
H
Provide reactions showing the following conversions: * see image
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- A 20.3 mL sample of 0.263 M triethylamine, (C2H5)3N, is titrated with 0.252 M hydrochloric acid. (1) At the titration midpoint, the pH is . (2) At the equivalence point, the pH is .arrow_forwardd. 3,4,5-trimethoxybenzoyl chloride . What is the order of decreasing reactivity towards nucleophilic acyl substitution for the arboxylic acid derivatives? (most reactive first) A. B. 0 0 O 0 0 H3C-C-O-C-CH3 H3C-C-N(CH3)2 H3C-C-OCH 3 (CH3)2CH-C-OCH3 I || ။ IV a. I, II, III, IV b. I, III, IV, II C. II, IV, III, I d. II, I, III, IV 0 0 0 0 0 R-C-O C-R R-C-NH2 R-C OR R-C-CI a. I, III, II, IV | 11 III IV b. II, III, I, IV c. III, II, I, IV d. IV, I, III, IIarrow_forwardB. d. a hydrate 4. Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry [4 ONLY]. A. CH₂OH PCC CH2Cl2 0 H KCN HCN 2arrow_forward
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