bartleby

Concept explainers

bartleby

Videos

Question
Book Icon
Chapter 17, Problem 86P

(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; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 17, Problem 86P , 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; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 17, Problem 86P , 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; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 17, Problem 86P , 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; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card;  Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition), Chapter 17, Problem 86P , additional homework tip  4

Blurred answer
Students have asked these similar questions
Consider the reactants below. Answer the following questions about the reaction mechanism and products. HO Cl
julietteyep@gmail.com X YSCU Grades for Juliette L Turner: Orc X 199 A ALEKS - Juliette Turner - Modul X A ALEKS - Juliette Turner - Modul x G butane newman projection - Gox + www-awa.aleks.com/alekscgi/x/Isl.exe/10_u-IgNslkr7j8P3jH-IBxzaplnN4HsoQggFsejpgqKoyrQrB2dKVAN-BcZvcye0LYa6eXZ8d4vVr8Nc1GZqko5mtw-d1MkNcNzzwZsLf2Tu9_V817y?10Bw7QYjlb il Scribbr citation APA SCU email Student Portal | Main Ryker-Learning WCU-PHARM D MySCU YSCU Canvas- SCU Module 4: Homework (Ch 9-10) Question 28 of 30 (1 point) | Question Attempt: 1 of Unlimited H₂SO heat OH The mechanism of this reaction involves two carbocation intermediates, A and B. Part 1 of 2 KHSO 4 rearrangement A heat B H₂O 2 OH Draw the structure of A. Check Search #t m Save For Later Juliet Submit Assignm 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Access
The electrons flow from the electron-rich atoms of the nucleophile to the electrons poor atoms of the alkyl halide. Identify the electron rich in the nucleophile. Enter the element symbol only, do not include any changes.

Chapter 17 Solutions

Organic Chemistry; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card; Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition)

Ch. 17.4 - Show how the following compounds can be...Ch. 17.5 - Prob. 13PCh. 17.5 - Prob. 14PCh. 17.6 - In the mechanism for cyanohydrin formation, why is...Ch. 17.6 - Prob. 16PCh. 17.6 - Prob. 17PCh. 17.6 - Show two ways to convert an alkyl halide into a...Ch. 17.7 - Prob. 20PCh. 17.7 - Prob. 21PCh. 17.7 - Prob. 22PCh. 17.7 - Prob. 23PCh. 17.8 - Prob. 24PCh. 17.9 - What reducing agents should be used to obtain the...Ch. 17.9 - Prob. 26PCh. 17.9 - Prob. 27PCh. 17.10 - Prob. 28PCh. 17.10 - Prob. 29PCh. 17.10 - Prob. 30PCh. 17.10 - The pKa of protonated acetone is about 7.5. and...Ch. 17.10 - Prob. 32PCh. 17.10 - Prob. 33PCh. 17.10 - Prob. 34PCh. 17.10 - Excess ammonia must be used when a primary amine...Ch. 17.10 - The compounds commonly known as amino acids are...Ch. 17.11 - Hydration of an aldehyde is also catalyzed by...Ch. 17.11 - Which ketone forms the most hydrate in an aqueous...Ch. 17.11 - When trichloroacetaldehyde is dissolved in water,...Ch. 17.12 - Which of the following are a. hermiacetals? b....Ch. 17.12 - Prob. 41PCh. 17.12 - Explain why an acetal can be isolated but most...Ch. 17.13 - Prob. 43PCh. 17.13 - Prob. 44PCh. 17.13 - What products would be formed from the proceedings...Ch. 17.13 - a. In a six-step synthesis, what is the yield of...Ch. 17.13 - Show how each of the following compounds could be...Ch. 17.15 - Prob. 48PCh. 17.17 - Prob. 50PCh. 17.18 - Prob. 51PCh. 17.19 - Prob. 52PCh. 17 - Draw the structure for each of the following: a....Ch. 17 - Prob. 54PCh. 17 - Prob. 55PCh. 17 - a. Show the reagents required to form the primary...Ch. 17 - Prob. 57PCh. 17 - Using cyclohexanone as the starting material,...Ch. 17 - Prob. 59PCh. 17 - 60. Show how each of the following compounds could...Ch. 17 - Fill in the boxes:Ch. 17 - Prob. 62PCh. 17 - Identify A through O:Ch. 17 - Prob. 64PCh. 17 - Prob. 65PCh. 17 - Prob. 66PCh. 17 - How many signals would the product of the...Ch. 17 - Prob. 68PCh. 17 - Prob. 69PCh. 17 - Prob. 70PCh. 17 - Prob. 71PCh. 17 - Prob. 72PCh. 17 - Prob. 73PCh. 17 - Prob. 74PCh. 17 - Prob. 75PCh. 17 - Prob. 76PCh. 17 - Prob. 77PCh. 17 - A compound gives the following IR spectrum. Upon...Ch. 17 - a. Propose a mechanism for the following reaction:...Ch. 17 - Prob. 80PCh. 17 - Prob. 81PCh. 17 - Prob. 82PCh. 17 - Prob. 83PCh. 17 - Prob. 84PCh. 17 - In the presence of an acid catalyst, acetaldehyde...Ch. 17 - Prob. 86PCh. 17 - Prob. 87PCh. 17 - Prob. 88PCh. 17 - A compound reacts with methylmagnesium bromide...Ch. 17 - Show how each of the following compounds can be...Ch. 17 - Prob. 91PCh. 17 - Prob. 92PCh. 17 - The pKa values of the carboxylic acid groups of...Ch. 17 - The Baylis-Hillman reaction is a DABCO...Ch. 17 - Prob. 95PCh. 17 - Prob. 96P
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
  • Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305080485
    Author:John E. McMurry
    Publisher:Cengage Learning
    Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305580350
    Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
    Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Characteristic Reactions of Benzene and Phenols; Author: Linda Hanson;https://www.youtube.com/watch?v=tjEqEjDd87E;License: Standard YouTube License, CC-BY
An Overview of Aldehydes and Ketones: Crash Course Organic Chemistry #27; Author: Crash Course;https://www.youtube.com/watch?v=-fBPX-4kFlw;License: Standard Youtube License