BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD)
BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD)
8th Edition
ISBN: 9781337687539
Author: Brown/Iverson/Anslyn/ Foote
Publisher: CENGAGE C
bartleby

Concept explainers

bartleby

Videos

Textbook Question
Book Icon
Chapter 16, Problem 16.23P

Draw structural formulas for (1) the alkyltriphenylphosphonium salt formed by treatment of each haloalkane with triphenylphosphine, (2) the phosphonium ylide formed by treatment of each phosphonium salt with butyllithium, and (3) the alkene formed by treatment of each phosphonium ylide with acetone.

Chapter 16, Problem 16.23P, Draw structural formulas for (1) the alkyltriphenylphosphonium salt formed by treatment of each , example  1

Chapter 16, Problem 16.23P, Draw structural formulas for (1) the alkyltriphenylphosphonium salt formed by treatment of each , example  2

Chapter 16, Problem 16.23P, Draw structural formulas for (1) the alkyltriphenylphosphonium salt formed by treatment of each , example  3

Chapter 16, Problem 16.23P, Draw structural formulas for (1) the alkyltriphenylphosphonium salt formed by treatment of each , example  4

Chapter 16, Problem 16.23P, Draw structural formulas for (1) the alkyltriphenylphosphonium salt formed by treatment of each , example  5

Chapter 16, Problem 16.23P, Draw structural formulas for (1) the alkyltriphenylphosphonium salt formed by treatment of each , example  6

(a)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structural formulas for the materials formed in the each steps in the Wittig reaction of  given reactant has to be drawn.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Wittig reaction is a reaction in which a nucleophilic elimination occurs after nucleophilic addition reaction. In this reaction an aldehyde or ketone reacts with a triphenyl phosphonium ylide (Wittig reagent) to give an alkene and triphenylphosphine oxide.

The reaction can be represented as shown below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  1

Mechanism:

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  2

Explanation of Solution

Given halo compound is shown below, 1,2 and 3 in the questions are the important steps in Wittig reaction.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  3

When treating this compound with triphenylphosphine corresponding alkyltriphenylphosphonium salt will form.

Thus, the alkyltriphenylphosphonium salt formed in the reaction (1) can be drawn as follows,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  4

Phosphonium ylide formed by treatment of this phosphonium salt with butyl lithium (2) can be drawn as shown below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  5

(3) The alkene formed by treatment of this phosphonium ylide with acetone is drawn below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  6

(b)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structural formulas for the materials formed in the each steps in the Wittig reaction of  given reactant has to be drawn.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Wittig reaction is a reaction in which a nucleophilic elimination occurs after nucleophilic addition reaction. In this reaction an aldehyde or ketone reacts with a triphenyl phosphonium ylide (Wittig reagent) to give an alkene and triphenylphosphine oxide.

The reaction can be represented as shown below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  7

Mechanism:

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  8

Explanation of Solution

Given halo compound is shown below, 1,2 and 3 in the questions are the important steps in Wittig reaction.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  9

When treating this compound with triphenylphosphine corresponding alkyltriphenylphosphonium salt will form.

Thus, the alkyltriphenylphosphonium salt formed in the reaction (1) can be drawn as follows,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  10

Phosphonium ylide formed by treatment of this phosphonium salt with butyl lithium (2) can be drawn as shown below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  11

(3) The alkene formed by treatment of this phosphonium ylide with acetone is drawn below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  12

(c)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structural formulas for the materials formed in the each steps in the Wittig reaction of  given reactant has to be drawn.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Wittig reaction is a reaction in which a nucleophilic elimination occurs after nucleophilic addition reaction. In this reaction an aldehyde or ketone reacts with a triphenyl phosphonium ylide (Wittig reagent) to give an alkene and triphenylphosphine oxide.

The reaction can be represented as shown below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  13

Mechanism:

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  14

Explanation of Solution

Given halo compound is shown below, 1,2 and 3 in the questions are the important steps in Wittig reaction.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  15

When treating this compound with triphenylphosphine corresponding alkyltriphenylphosphonium salt will form.

Thus, the alkyltriphenylphosphonium salt formed in the reaction (1) can be drawn as follows,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  16

Phosphonium ylide formed by treatment of this phosphonium salt with butyl lithium (2) can be drawn as shown below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  17

(3) The alkene formed by treatment of this phosphonium ylide with acetone is drawn below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  18

(d)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structural formulas for the materials formed in the each steps in the Wittig reaction of  given reactant has to be drawn.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Wittig reaction is a reaction in which a nucleophilic elimination occurs after nucleophilic addition reaction. In this reaction an aldehyde or ketone reacts with a triphenyl phosphonium ylide (Wittig reagent) to give an alkene and triphenylphosphine oxide.

The reaction can be represented as shown below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  19

Mechanism:

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  20

Explanation of Solution

Given halo compound is shown below, 1,2 and 3 in the questions are the important steps in Wittig reaction.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  21

When treating this compound with triphenylphosphine corresponding alkyltriphenylphosphonium salt will form.

Thus, the alkyltriphenylphosphonium salt formed in the reaction (1) can be drawn as follows,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  22

Phosphonium ylide formed by treatment of this phosphonium salt with butyl lithium (2) can be drawn as shown below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  23

(3) The alkene formed by treatment of this phosphonium ylide with acetone is drawn below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  24

(e)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structural formulas for the materials formed in the each steps in the Wittig reaction of  given reactant has to be drawn.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Wittig reaction is a reaction in which a nucleophilic elimination occurs after nucleophilic addition reaction. In this reaction an aldehyde or ketone reacts with a triphenyl phosphonium ylide (Wittig reagent) to give an alkene and triphenylphosphine oxide.

The reaction can be represented as shown below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  25

Mechanism:

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  26

Explanation of Solution

Given halo compound is shown below, 1,2 and 3 in the questions are the important steps in Wittig reaction.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  27

When treating this compound with triphenylphosphine corresponding alkyltriphenylphosphonium salt will form.

Thus, the alkyltriphenylphosphonium salt formed in the reaction (1) can be drawn as follows,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  28

Phosphonium ylide formed by treatment of this phosphonium salt with butyl lithium (2) can be drawn as shown below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  29

(3) The alkene formed by treatment of this phosphonium ylide with acetone is drawn below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  30

(f)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structural formulas for the materials formed in the each steps in the Wittig reaction of  given reactant has to be drawn.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Wittig reaction is a reaction in which a nucleophilic elimination occurs after nucleophilic addition reaction. In this reaction an aldehyde or ketone reacts with a triphenyl phosphonium ylide (Wittig reagent) to give an alkene and triphenylphosphine oxide.

The reaction can be represented as shown below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  31

Mechanism:

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  32

Explanation of Solution

Given halo compound is shown below, 1,2 and 3 in the questions are the important steps in Wittig reaction.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  33

When treating this compound with triphenylphosphine corresponding alkyltriphenylphosphonium salt will form.

Thus, the alkyltriphenylphosphonium salt formed in the reaction (1) can be drawn as follows,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  34

Phosphonium ylide formed by treatment of this phosphonium salt with butyl lithium (2) can be drawn as shown below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  35

(3) The alkene formed by treatment of this phosphonium ylide with acetone is drawn below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 16, Problem 16.23P , additional homework tip  36

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!
Students have asked these similar questions
Acetylene reacts with sodium amide in the presence of propyl halide produces aldehyde produces ketones It produces 2-pentane
11) Synthesize 2-methyl-3-hydroxycyclohexone from cyclohexone, methyl iodide, and inorganic precursors.
Describe a sequence of reactions by which cis-2-pentene could be prepared from acetylene.

Chapter 16 Solutions

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD)

Ch. 16.8 - The given mechanism of transamination reaction is...Ch. 16.8 - Prob. DQCh. 16.8 - Prob. EQCh. 16.8 - The given mechanism of transamination reaction is...Ch. 16.9 - Predict the position of the following equilibrium.Ch. 16.9 - Draw a structural formula for the keto form of...Ch. 16.10 - Prob. 16.11PCh. 16.11 - What aldehyde or ketone gives these alcohols upon...Ch. 16.11 - Prob. 16.13PCh. 16 - Prob. 16.14PCh. 16 - Prob. 16.15PCh. 16 - The infrared spectrum of compound A, C6H12O, shows...Ch. 16 - Following are 1H-NMR spectra for compounds B...Ch. 16 - Draw structural formulas for the product formed by...Ch. 16 - Suggest a synthesis for the following alcohols...Ch. 16 - Show how to synthesize the following alcohol using...Ch. 16 - 1-Phenyl-2-butanol is used in perfumery. Show how...Ch. 16 - Prob. 16.22PCh. 16 - Draw structural formulas for (1) the...Ch. 16 - Show how to bring about the following conversions...Ch. 16 - Prob. 16.25PCh. 16 - Wittig reactions with the following -chloroethers...Ch. 16 - Prob. 16.27PCh. 16 - Prob. 16.28PCh. 16 - 5-Hydroxyhexanal forms a six-membered cyclic...Ch. 16 - Prob. 16.30PCh. 16 - Prob. 16.31PCh. 16 - Propose a mechanism to account for the formation...Ch. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - Show how to bring about the following conversion.Ch. 16 - A primary or secondary alcohol can be protected by...Ch. 16 - Prob. 16.37PCh. 16 - Prob. 16.38PCh. 16 - Prob. 16.39PCh. 16 - Prob. 16.40PCh. 16 - The following molecule belongs to a class of...Ch. 16 - When cis-2-decalone is dissolved in ether...Ch. 16 - Prob. 16.43PCh. 16 - Prob. 16.44PCh. 16 - The following bicyclic ketone has two -carbons and...Ch. 16 - Propose a mechanism for this reaction.Ch. 16 - The base-promoted rearrangement of an -haloketone...Ch. 16 - If the Favorskii rearrangement of...Ch. 16 - (R)-Pulegone, readily available from pennyroyal...Ch. 16 - (R)-Pulegone is converted to (R)-citronellic acid...Ch. 16 - Starting with cyclohexanone, show how to prepare...Ch. 16 - Show how to convert cyclopentanone to these...Ch. 16 - Prob. 16.53PCh. 16 - Prob. 16.54PCh. 16 - Prob. 16.55PCh. 16 - Following is the structural formula of Surfynol, a...Ch. 16 - Prob. 16.57PCh. 16 - Propose a mechanism for this isomerization.Ch. 16 - Starting with acetylene and 1-bromobutane as the...Ch. 16 - Prob. 16.60PCh. 16 - Prob. 16.61PCh. 16 - Prob. 16.62PCh. 16 - Prob. 16.63PCh. 16 - Prob. 16.64PCh. 16 - All rearrangements we have discussed so far have...Ch. 16 - In dilute aqueous base, (R)-glyceraldehyde is...Ch. 16 - Treatment of -D-glucose with methanol in the...Ch. 16 - Treating a Grignard reagent with carbon dioxide...Ch. 16 - Prob. 16.69PCh. 16 - Prob. 16.70PCh. 16 - Prob. 16.71PCh. 16 - Prob. 16.72PCh. 16 - Write the products of the following sequences of...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Prob. 16.78PCh. 16 - Prob. 16.79PCh. 16 - Prob. 16.80PCh. 16 - Prob. 16.81P
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:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning
Alcohols, Ethers, and Epoxides: Crash Course Organic Chemistry #24; Author: Crash Course;https://www.youtube.com/watch?v=j04zMFwDeDU;License: Standard YouTube License, CC-BY