Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Question
Chapter 20.17, Problem 32P
Interpretation Introduction
Interpretation:
The reason for hydroxyl group at third Carbon is more acidic than second Carbon in vitamin C is to be explained.
Concept Introduction:
Acidity is defined as the property to accept electrons or tendency to donate hydrogen ion from the molecule. Compounds having higher tendency to donate hydrogen ion is more acidic than the compounds having less tendency to donate hydrogen ion.
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Draw the structures of aspirin, caffeine, and acetaminophen. Give the hybridization of each carbon atom and state which is acidic, weakly acidic, and basic. Identify the sites on each compound that make each acidic, weakly acidic, and basic.
Provide an explanation without using the pka values :
Why is phenol stronger acid than butanoic acid?
Calculate the pKa of each acid and indicate which is the stronger acid.
C6O2H8, Ka = 1.7 x 10–5
C2O4H2, Ka = 5.9 x 10–2
Chapter 20 Solutions
Organic Chemistry (8th Edition)
Ch. 20.1 - Prob. 1PCh. 20.2 - Prob. 2PCh. 20.2 - Prob. 3PCh. 20.3 - Prob. 4PCh. 20.3 - Prob. 5PCh. 20.3 - Prob. 6PCh. 20.4 - Prob. 7PCh. 20.4 - Prob. 8PCh. 20.5 - Prob. 9PCh. 20.5 - Prob. 10P
Ch. 20.5 - Prob. 11PCh. 20.6 - Prob. 12PCh. 20.6 - Prob. 13PCh. 20.6 - Prob. 14PCh. 20.7 - Prob. 15PCh. 20.8 - Prob. 16PCh. 20.9 - Prob. 18PCh. 20.10 - Prob. 20PCh. 20.10 - Prob. 21PCh. 20.10 - Prob. 22PCh. 20.11 - Prob. 23PCh. 20.11 - Prob. 24PCh. 20.12 - Prob. 25PCh. 20.12 - Prob. 26PCh. 20.14 - Prob. 28PCh. 20.15 - Prob. 29PCh. 20.15 - Prob. 30PCh. 20.16 - Prob. 31PCh. 20.17 - Prob. 32PCh. 20.18 - Refer to Figure 20.5 to answer the following...Ch. 20 - Prob. 34PCh. 20 - Prob. 35PCh. 20 - Prob. 36PCh. 20 - Prob. 37PCh. 20 - Prob. 38PCh. 20 - Prob. 39PCh. 20 - Prob. 40PCh. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - Prob. 43PCh. 20 - Prob. 44PCh. 20 - Prob. 45PCh. 20 - Prob. 46PCh. 20 - Prob. 47PCh. 20 - Prob. 48PCh. 20 - The 1H NMR spectrum of D-glucose in D2O exhibits...Ch. 20 - Prob. 50PCh. 20 - Prob. 51PCh. 20 - Prob. 52PCh. 20 - Prob. 53PCh. 20 - Prob. 54PCh. 20 - Prob. 55PCh. 20 - Prob. 56PCh. 20 - Prob. 57PCh. 20 - Prob. 58PCh. 20 - Prob. 59PCh. 20 - Prob. 60PCh. 20 - Prob. 61PCh. 20 - A hexose is obtained when the residue of a shrub...Ch. 20 - Prob. 63PCh. 20 - Prob. 64PCh. 20 - Prob. 65PCh. 20 - Prob. 66PCh. 20 - Prob. 67PCh. 20 - Prob. 68PCh. 20 - Prob. 69PCh. 20 - Prob. 70PCh. 20 - Prob. 71PCh. 20 - Prob. 72PCh. 20 - Prob. 73P
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- Does alcohol, ketones, and aldehydes considered acidic or a basic?arrow_forwardDetermine which of the following bases is strong enough to deprotonate acetonitrile (CH3CN), so that equilibrium favors the products:(a) NaH; (b) Na2CO3; (c) NaOH; (d) NaNH2; (e) NaHCO3.arrow_forwardIf compound A has a ka of 3.0 x 10-11 , compound B has a ka of 1.1 x 10-10 and compound C has a ka of 1.8 x 10-5, which compound is the weakest acid?arrow_forward
- The pKa of ascorbic acid (vitamin C, page 55) is 4.17, showing that it is slightly more acidic than acetic acid (CH3COOH, pKa 4.74). Compare the most stable conjugate base of ascorbic acid with the conjugate base of acetic acid, and suggest why these two compounds have similar acidities, even though ascorbic acid lacks the carboxylic acid (COOH) group.arrow_forwardCholic acid, a compound called a bile acid, is converted to a bile salt in the body. Bile salts have properties similar to soaps, and they help transport lipids through aqueous solutions. Explain why this is so.arrow_forwardWhy is it safe for us to consume foods like vinegar that contain acetic acids?arrow_forward
- When ethylamine, a weak base (Kb=4.3104) , reacts with formic acid, a weak acid (Ka=1.8104) , the following reaction takes place: CH3CH2NH2(aq)+HCOOH(aq)CH3CH2NH3+(aq)+HCOO(aq) Calculate K for this reaction.arrow_forwardWhat is true regarding protein backbones? The protein backbone is different for each protein and contains both amine and carboxylic acid functional groups The protein backbone is the same for each protein and contains both amine and carboxylic acid functional groups The protein backbone is different for each protein and contains amide functional groups The protein backbone is the same for each protein and contains amide functional groupsarrow_forwardAccount for the fact that one carboxyl group is a considerably stronger acid than the other carboxyl group.arrow_forward
- List the Nitrogen from most to least basic. Explain whyarrow_forward4-chlorophenol has a pka of 9.41 and diethylmethylamine has a pkb of 3.65. A 1.0M solution of diethylmethylammonium-4-chlorophenolate would be strongly acidic neutral weakly acidic weakly basic strongly basicarrow_forwardOne of the three molecules is much more acidic than the other two. Identify the molecule and explain why it is so much more acidic that the other two. H Harrow_forward
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