Organic Chemistry (8th Edition)
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 16, Problem 89P

(a)

Interpretation Introduction

Interpretation:

The carbonyl carbon and phosphonium ylide that are needed to synthesize the given compound has to be identified.

Concept introduction:

Wittig reaction:

Witting reaction is the reaction between the carbonyl carbon of aldehyde or ketone and the phosphonium ylide to give an alkene.  Wittig reaction is a very useful method to synthesize the compound which can’t be synthesis easily by other methods.

Specific phosphonium ylide can be prepared for specific alkene synthesis.  The triphenylphosphine is reacted with alkyl halide that has required numbers of carbon.  A strong base such as sodium hydride or butyllithium is added to remove proton of carbon adjacent to the phosphorus atom.  The carbon of prepared phosphonium ylide have nucleophilic character and get attached to the carbonyl carbon and carbonyl oxygen get attached to the positively charged phosphorous.  Triphenylphosphine oxide gets eliminated resulting in the formation of the alkene.

The mechanism of the witting reaction is:

Organic Chemistry (8th Edition), Chapter 16, Problem 89P , additional homework tip  1

(b)

Interpretation Introduction

Interpretation:

The carbonyl carbon and phosphonium ylide that are needed to synthesize the given compound has to be identified.

Concept introduction:

Wittig reaction:

Witting reaction is the reaction between the carbonyl carbon of aldehyde or ketone and the phosphonium ylide to give an alkene.  Wittig reaction is a very useful method to synthesize the compound which can’t be synthesis easily by other methods.

Specific phosphonium ylide can be prepared for specific alkene synthesis.  The triphenylphosphine is reacted with alkyl halide that has required numbers of carbon.  A strong base such as sodium hydride or butyllithium is added to remove proton of carbon adjacent to the phosphorus atom.  The carbon of prepared phosphonium ylide have nucleophilic character and get attached to the carbonyl carbon and carbonyl oxygen get attached to the positively charged phosphorous.  Triphenylphosphine oxide gets eliminated resulting in the formation of the alkene.

The mechanism of the witting reaction is:

Organic Chemistry (8th Edition), Chapter 16, Problem 89P , additional homework tip  2

(c)

Interpretation Introduction

Interpretation:

The carbonyl carbon and phosphonium ylide that are needed to synthesize the given compound has to be identified.

Concept introduction:

Wittig reaction:

Witting reaction is the reaction between the carbonyl carbon of aldehyde or ketone and the phosphonium ylide to give an alkene.  Wittig reaction is a very useful method to synthesize the compound which can’t be synthesis easily by other methods.

Specific phosphonium ylide can be prepared for specific alkene synthesis.  The triphenylphosphine is reacted with alkyl halide that has required numbers of carbon.  A strong base such as sodium hydride or butyllithium is added to remove proton of carbon adjacent to the phosphorus atom.  The carbon of prepared phosphonium ylide have nucleophilic character and get attached to the carbonyl carbon and carbonyl oxygen get attached to the positively charged phosphorous.  Triphenylphosphine oxide gets eliminated resulting in the formation of the alkene.

The mechanism of the witting reaction is:

Organic Chemistry (8th Edition), Chapter 16, Problem 89P , additional homework tip  3

(d)

Interpretation Introduction

Interpretation:

The carbonyl carbon and phosphonium ylide that are needed to synthesize the given compound has to be identified.

Concept introduction:

Wittig reaction:

Witting reaction is the reaction between the carbonyl carbon of aldehyde or ketone and the phosphonium ylide to give an alkene.  Wittig reaction is a very useful method to synthesize the compound which can’t be synthesis easily by other methods.

Specific phosphonium ylide can be prepared for specific alkene synthesis.  The triphenylphosphine is reacted with alkyl halide that has required numbers of carbon.  A strong base such as sodium hydride or butyllithium is added to remove proton of carbon adjacent to the phosphorus atom.  The carbon of prepared phosphonium ylide have nucleophilic character and get attached to the carbonyl carbon and carbonyl oxygen get attached to the positively charged phosphorous.  Triphenylphosphine oxide gets eliminated resulting in the formation of the alkene.

The mechanism of the witting reaction is:

Organic Chemistry (8th Edition), Chapter 16, Problem 89P , additional homework tip  4

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Chapter 16 Solutions

Organic Chemistry (8th Edition)

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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