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)
Arrange the following compounds in the increasing order of their acid strength: p-cresol, p-nitrophenol, phenol
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.
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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- 29) Consider the following acid-base reaction: он Cно Na A | в 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) most stable leaststablearrow_forwardThe following questions concern ethyl (2-oxocyclohexane)carboxylate.(a) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by a Dieckmann cyclization.(b) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by acylation of a ketone.(c) Write structural formulas for the two most stable enol forms of ethyl (2-oxocyclohexane)carboxylate.(d) Write the three most stable resonance contributors to the most stable enolate derived from ethyl (2-oxocyclohexane)carboxylate.(e) Show how you could use ethyl (2-oxocyclohexane)carboxylate to prepare 2-methylcyclohexanone.(f) Give the structure of the product formed on treatment of ethyl (2-oxocyclohexane)-carboxylate with acrolein (H2C=CHCH=O) in ethanol in the presence of sodium ethoxidearrow_forward11 Considering the three structures depicted below, which of the following statements is entirely True? OH SH OH C B Molecule A is a phenol while C is a sulfonic acid which C being more acidic than A. Molecules A and C are phenols and are equally acidic. Molecules A and C are phenols with A being more acidic than C. Molecules A and B are alcohols with A being more acidic than B. Molecule A is a phenol while C is a thiol with C being more acidic than A.arrow_forward
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