Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 6, Problem 6.80P
Interpretation Introduction
Interpretation:
The stronger acid between
Concept introduction:
The acid whose conjugate base is most stable is the stronger acid. The adjacent electron withdrawing group delocalizes the negative charge on the conjugate base and stabilizes it through the resonance effect. Greater the resonance stabilization, stronger is the acid.
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Students have asked these similar questions
Which do you predict will be a stronger acid:
m-hydroxybenzaldehyde or p-hydroxybenzaldehyde?
Explain.
ОН
OH
m-Hydroxybenzaldehyde
p-Hydroxybenzaldehyde
h) Which is a weaker base and why?
Pyridine
Pyrrole
i) Name the following compounds.
H2N
A
B
NH2
Phenol has a pka = 10.0. 4-Hydroxybenzaldehyde has a pka = 7.3. Draw resonance forms of the
conjugate base of both and explain why 4-hydroxybenzaldehyde is more acidic. (Acidic H is underlined.)
OH
phenol
OH
-H*
- H*
4-hyroxybenzaldehyde
Chapter 6 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
Ch. 6 - Prob. 6.1PCh. 6 - Prob. 6.2PCh. 6 - Prob. 6.3PCh. 6 - Prob. 6.4PCh. 6 - Prob. 6.5PCh. 6 - Prob. 6.6PCh. 6 - Prob. 6.7PCh. 6 - Prob. 6.8PCh. 6 - Prob. 6.9PCh. 6 - Prob. 6.10P
Ch. 6 - Prob. 6.11PCh. 6 - Prob. 6.12PCh. 6 - Prob. 6.13PCh. 6 - Prob. 6.14PCh. 6 - Prob. 6.15PCh. 6 - Prob. 6.16PCh. 6 - Prob. 6.17PCh. 6 - Prob. 6.18PCh. 6 - Prob. 6.19PCh. 6 - Prob. 6.20PCh. 6 - Prob. 6.21PCh. 6 - Prob. 6.22PCh. 6 - Prob. 6.23PCh. 6 - Prob. 6.24PCh. 6 - Prob. 6.25PCh. 6 - Prob. 6.26PCh. 6 - Prob. 6.27PCh. 6 - Prob. 6.28PCh. 6 - Prob. 6.29PCh. 6 - Prob. 6.30PCh. 6 - Prob. 6.31PCh. 6 - Prob. 6.32PCh. 6 - Prob. 6.33PCh. 6 - Prob. 6.34PCh. 6 - Prob. 6.35PCh. 6 - Prob. 6.36PCh. 6 - Prob. 6.37PCh. 6 - Prob. 6.38PCh. 6 - Prob. 6.39PCh. 6 - Prob. 6.40PCh. 6 - Prob. 6.41PCh. 6 - Prob. 6.42PCh. 6 - Prob. 6.43PCh. 6 - Prob. 6.44PCh. 6 - Prob. 6.45PCh. 6 - Prob. 6.46PCh. 6 - Prob. 6.47PCh. 6 - Prob. 6.48PCh. 6 - Prob. 6.49PCh. 6 - Prob. 6.50PCh. 6 - Prob. 6.51PCh. 6 - Prob. 6.52PCh. 6 - Prob. 6.53PCh. 6 - Prob. 6.54PCh. 6 - Prob. 6.55PCh. 6 - Prob. 6.56PCh. 6 - Prob. 6.57PCh. 6 - Prob. 6.58PCh. 6 - Prob. 6.59PCh. 6 - Prob. 6.60PCh. 6 - Prob. 6.61PCh. 6 - Prob. 6.62PCh. 6 - Prob. 6.63PCh. 6 - Prob. 6.64PCh. 6 - Prob. 6.65PCh. 6 - Prob. 6.66PCh. 6 - Prob. 6.67PCh. 6 - Prob. 6.68PCh. 6 - Prob. 6.69PCh. 6 - Prob. 6.70PCh. 6 - Prob. 6.71PCh. 6 - Prob. 6.72PCh. 6 - Prob. 6.73PCh. 6 - Prob. 6.74PCh. 6 - Prob. 6.75PCh. 6 - Prob. 6.76PCh. 6 - Prob. 6.77PCh. 6 - Prob. 6.78PCh. 6 - Prob. 6.79PCh. 6 - Prob. 6.80PCh. 6 - Prob. 6.81PCh. 6 - Prob. 6.82PCh. 6 - Prob. 6.83PCh. 6 - Prob. 6.84PCh. 6 - Prob. 6.85PCh. 6 - Prob. 6.86PCh. 6 - Prob. 6.87PCh. 6 - Prob. 6.88PCh. 6 - Prob. 6.1YTCh. 6 - Prob. 6.2YTCh. 6 - Prob. 6.3YTCh. 6 - Prob. 6.4YTCh. 6 - Prob. 6.5YTCh. 6 - Prob. 6.6YTCh. 6 - Prob. 6.7YTCh. 6 - Prob. 6.8YTCh. 6 - Prob. 6.9YTCh. 6 - Prob. 6.10YTCh. 6 - Prob. 6.11YTCh. 6 - Prob. 6.12YTCh. 6 - Prob. 6.13YTCh. 6 - Prob. 6.14YTCh. 6 - Prob. 6.15YTCh. 6 - Prob. 6.16YTCh. 6 - Prob. 6.17YTCh. 6 - Prob. 6.18YTCh. 6 - Prob. 6.19YTCh. 6 - Prob. 6.20YT
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- Complete each acid-base reaction and predict whether the position of equilibrium lies toward the left or toward the right. (a) CH3CCH+CH3CH2ONa+CH3CH3OH (b) CH3CCCH2CH2OH+Na+NH2NH3(l)arrow_forwardWhich of the following substituted phenol is the strong acid? |- p-nitrophenol Il-p-methoxyphenol III- p-ethylphenol IV- p-methylphenol * II IV All have the same acidityarrow_forwardWhich compound is the strongest base? NH2 NH2 NH2 NH2 `NH2 O2N III IV V II O V O II O IVarrow_forward
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