Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 12, Problem 4PP
PRACTICE PROBLEM 12.4
Predict the products of the following acid–base reactions. Using
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HO
CH30 Na
A
+
B
O,N
pK =7
(a) Provide structures for A and B (including nonbonding electron pairs and formal
charges where necessary), where A is the conjugate acid and B is the conjugate base
of the reaction.
Answer:
(b) Provide and arrow pushing mechanism to show how A and B are formed.
Answer:
(c) Will the reaction proceed from left to right (i.e. are A and B favoured at equilibrium)?
Explain your answer.
Answer:
(d) Draw all important resonance contributors of the conjugate base B. Rank the
contributors from most stable to least stable (if contributors are equally stable indicate
this with an equals sign)
H3C.
OH
HO Na
+
pK = 9
(a) Provide structures for A and B (including nonbonding electron pairs and formal
charges where necessary), where A is the conjugate acid and B is the conjugate base
of the reaction.
Answer:
(b) Provide and arrow pushing mechanism to show how A and B are formed.
Answer:
(c) Will the reaction proceed from left to right (i.e. are A and B favoured at equilibrium)?
Explain your answer.
Answer:
(d) Draw all important resonance contributors of the conjugate base B.
The table shows the base ionisation constant, Kb, for several selected compounds.
(a)
Compound
C6H5NH2
Kb
3.8x10-10
1.7x10-6
N2H4
NH3
1.8x10-5
NH2OH
1.1x10-8
i.
Arrange the compounds in order of increasing strength of base.
ii.
Give the structure of conjugate acid for each compound and arrange them
in order of increasing strength of acid.
(b) The percentage ionisation of 0.010 M NH3 solution was 4.2 % ionisation.
Calculate Kb.
1.8x105
Chapter 12 Solutions
Organic Chemistry
Ch. 12 - Prob. 1PPCh. 12 - Prob. 2PPCh. 12 - Prob. 3PPCh. 12 - PRACTICE PROBLEM 12.4 Predict the products of the...Ch. 12 - Prob. 5PPCh. 12 - Prob. 6PPCh. 12 - Practice Problem 12.7
Provide retrosynthetic...Ch. 12 - Prob. 8PPCh. 12 - What products would you expect from the reaction...Ch. 12 - What products would you expect from the reaction...
Ch. 12 - What product (or products) would be formed from...Ch. 12 - Prob. 12PCh. 12 - 12.13 Write reaction conditions and the product...Ch. 12 - Prob. 14PCh. 12 - Predict the organic product from each of the...Ch. 12 - Predict the organic product from each of the...Ch. 12 - Predict the organic product from each of the...Ch. 12 - Predict the major organic product from each of the...Ch. 12 - Synthesize each of the following compounds from...Ch. 12 - Prob. 20PCh. 12 - 21. Write a mechanism for the following reaction....Ch. 12 - Prob. 22PCh. 12 - 23. What organic products A-H would you expect...Ch. 12 - Prob. 24PCh. 12 - Show how 1-pentanol could be transformed into each...Ch. 12 - Provide the reagents needed to accomplish...Ch. 12 - Prob. 27PCh. 12 - For each of the following alcohols, write a...Ch. 12 - Prob. 29PCh. 12 - Prob. 30PCh. 12 - Prob. 31PCh. 12 - Prob. 32PCh. 12 - Predict the major organic product from each of the...Ch. 12 - 34. Synthesize the following compound using...Ch. 12 - Prob. 35PCh. 12 - Prob. 36PCh. 12 - 37. Explain how and IR spectroscopy could be used...Ch. 12 - 38. An unknown X shows a broad absorption band in...Ch. 12 - Prob. 39PCh. 12 - The problem below is directed toward devising a...
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