EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 16, Problem 98P

(a)

Interpretation Introduction

Interpretation:

Reaction mechanism has to be proposed for the given reaction.

Concept introduction: A cyclic acetal is formed on a combination of an aldehyde and a diol. An acetal is a protecting group for aldehyde and ketones.  A cyclic acetal on heating with aqueous acid gives back aldehyde and diol.  Heating in aqueous acidic medium causes the deprotection of aldehyde group.

(b)

Interpretation Introduction

Interpretation:

Reaction mechanism has to be proposed for the given reaction.

Concept introduction: Nucleophile CH3CH2SH is a weak base.  The weak base forms a conjugate addition product.  The conjugate addition product undergoes tautomerism.  Keto-enol tautomerism results in a gain of aromaticity in the molecule.  Therefore in this particular case enol form is more stable than the keto form.

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Chapter 16 Solutions

EBK ORGANIC CHEMISTRY

Ch. 16.4 - Show how the following compounds can be...Ch. 16.4 - Prob. 13PCh. 16.4 - Prob. 14PCh. 16.4 - In the mechanism for cyanohydrin formation, why is...Ch. 16.4 - Prob. 16PCh. 16.4 - Prob. 17PCh. 16.4 - Show two ways to convert an alkyl halide into a...Ch. 16.5 - Prob. 20PCh. 16.5 - Prob. 21PCh. 16.5 - Prob. 22PCh. 16.5 - Prob. 23PCh. 16.6 - Prob. 24PCh. 16.7 - What reducing agents should be used to obtain the...Ch. 16.7 - Prob. 26PCh. 16.8 - Prob. 27PCh. 16.8 - Prob. 28PCh. 16.8 - Prob. 29PCh. 16.8 - The pKa of protonated acetone is about 7.5. and...Ch. 16.8 - Prob. 31PCh. 16.8 - Prob. 32PCh. 16.8 - Prob. 33PCh. 16.8 - Excess ammonia must be used when a primary amine...Ch. 16.8 - The compounds commonly known as amino acids are...Ch. 16.9 - Hydration of an aldehyde is also catalyzed by...Ch. 16.9 - Which ketone forms the most hydrate in an aqueous...Ch. 16.9 - When trichloroacetaldehyde is dissolved in water,...Ch. 16.9 - Which of the following are a. hermiacetals? b....Ch. 16.9 - Prob. 40PCh. 16.9 - Explain why an acetal can be isolated but most...Ch. 16.10 - Prob. 42PCh. 16.10 - Prob. 43PCh. 16.10 - What products would be formed from the proceedings...Ch. 16.10 - a. In a six-step synthesis, what is the yield of...Ch. 16.10 - Show how each of the following compounds could be...Ch. 16.12 - Prob. 47PCh. 16.13 - Prob. 49PCh. 16.14 - Prob. 50PCh. 16.15 - Prob. 51PCh. 16.16 - Prob. 52PCh. 16 - Draw the structure for each of the following: a....Ch. 16 - Prob. 54PCh. 16 - Prob. 55PCh. 16 - Prob. 56PCh. 16 - a. Show the reagents required to form the primary...Ch. 16 - Prob. 58PCh. 16 - Prob. 59PCh. 16 - Using cyclohexanone as the starting material,...Ch. 16 - Propose a mechanism for each of the following...Ch. 16 - Show how each of the following compounds can be...Ch. 16 - Fill in the boxes:Ch. 16 - Prob. 64PCh. 16 - Identify A through O:Ch. 16 - Prob. 66PCh. 16 - Prob. 67PCh. 16 - Prob. 68PCh. 16 - How many signals would the product of the...Ch. 16 - Prob. 70PCh. 16 - Prob. 71PCh. 16 - Prob. 72PCh. 16 - Prob. 73PCh. 16 - Prob. 74PCh. 16 - Prob. 75PCh. 16 - Prob. 76PCh. 16 - Prob. 77PCh. 16 - Prob. 78PCh. 16 - Draw structure for A-D for each of the following:Ch. 16 - Prob. 80PCh. 16 - a. Propose a mechanism for the following reaction:...Ch. 16 - Prob. 82PCh. 16 - A compound gives the following IR spectrum. Upon...Ch. 16 - How can be following compounds be prepared from...Ch. 16 - Prob. 85PCh. 16 - Prob. 86PCh. 16 - Prob. 87PCh. 16 - In the presence of an acid catalyst, acetaldehyde...Ch. 16 - Prob. 89PCh. 16 - Prob. 90PCh. 16 - Prob. 91PCh. 16 - A compound reacts with methylmagnesium bromide...Ch. 16 - Show how each of the following compounds can be...Ch. 16 - Prob. 94PCh. 16 - The pKa values of the carboxylic acid groups of...Ch. 16 - The Baylis-Hillman reaction is a DABCO...Ch. 16 - Prob. 97PCh. 16 - Prob. 98P
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