Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 16, Problem 35P

Show how benzaldehyde could be synthesized from each of the following:

(a) Benzyl alcohol

(b) Benzoic acid

(c) Phenylethyne

(d) Phenylethene (styrene)

(e) C 6 H 5 C O 2 C H 3

(f) C 6 H 5 C N

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The following compound undergoes Benzilic Acid Rearrangementto yield a hydroxyacid salt. Propose a mechanism for the reaction, write the major product, and provide an explanation as to the preference of migration of one R group over the other.
Shown below is the 1H NMR spectrum of the alkyl bromide used to make the phosphonium ylide that reacts with a ketone in a Wittig reaction to form acompound with molecular formula C11H14. What product is obtained from the Wittig reaction?
Shown below is the 1H NMR spectrum of the alkyl bromide used to make the phosphonium ylide that reacts with a ketone in a Wittig reaction to form a compound with molecular formula C11H14. What product is obtained from the Wittig reaction?

Chapter 16 Solutions

Organic Chemistry

Ch. 16 - Prob. 11PPCh. 16 - Practice Problem 16.12 What product would be...Ch. 16 - Prob. 13PPCh. 16 - Practice Problem 16.14 Dihydropyran reacts readily...Ch. 16 - Practice Problem 16.15 Show how you might use...Ch. 16 - Practice Problem 16.16 (a) Show how you might...Ch. 16 - Practice Problem 16.17 In addition to...Ch. 16 - Practice Problem 16.18 Triphenylphosphine can be...Ch. 16 - Prob. 19PPCh. 16 - PRACTICE PROBLEM 16.20 Give the structure of the...Ch. 16 - PRACTICE PROBLEM 16.21 What would be the major...Ch. 16 - Prob. 22PCh. 16 - 16.23 Write structural formulas for the products...Ch. 16 - Give structural formulas for the products formed...Ch. 16 - 16.25 What products would be obtained when...Ch. 16 - Predict the major organic product from each of the...Ch. 16 - 16.27 Predict the major product from each of the...Ch. 16 - 16.28 Predict the major product from each of the...Ch. 16 - Prob. 29PCh. 16 - 16.30 Write detailed mechanisms for each of the...Ch. 16 - Prob. 31PCh. 16 - Prob. 32PCh. 16 - Show how you would convert benzaldehyde into each...Ch. 16 - 16.34 Show how ethyl phenyl ketone could be...Ch. 16 - Show how benzaldehyde could be synthesized from...Ch. 16 - Give structures for compounds AE. Cyclohexanol...Ch. 16 - Prob. 37PCh. 16 - Prob. 38PCh. 16 - Prob. 39PCh. 16 - Prob. 40PCh. 16 - Prob. 41PCh. 16 - Prob. 42PCh. 16 - 16.43 The structure of the sex pheromone...Ch. 16 - Provide reagents that would accomplish each of the...Ch. 16 - Write a detailed mechanism for the following...Ch. 16 - Prob. 46PCh. 16 - Dutch elm disease is caused by a fungus...Ch. 16 - Prob. 48PCh. 16 - Compounds W and X are isomers; they have the...Ch. 16 - Compounds Y and Z are isomers with the molecular...Ch. 16 - Compound A (C9H18O) forms a phenylhydrazone, but...Ch. 16 - Compound B (C8H12O2) shows a strong carbonyl...Ch. 16 - Prob. 53PCh. 16 - Prob. 54PCh. 16 - Prob. 55PCh. 16 - (a) What would be the frequencies of the two...Ch. 16 - Prob. 57PCh. 16 - Prob. LGP
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