EP ORGANIC CHEMISTRY-OWL V2 ACCESS
EP ORGANIC CHEMISTRY-OWL V2 ACCESS
8th Edition
ISBN: 9781305582453
Author: Brown
Publisher: Cengage Learning
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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,

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , Chapter 16, Problem 16.23P , additional homework tip  1

Mechanism:

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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.

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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,

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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,

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , Chapter 16, Problem 16.23P , additional homework tip  5

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

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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,

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , Chapter 16, Problem 16.23P , additional homework tip  7

Mechanism:

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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.

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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,

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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,

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , Chapter 16, Problem 16.23P , additional homework tip  11

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

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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,

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , Chapter 16, Problem 16.23P , additional homework tip  13

Mechanism:

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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.

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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,

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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,

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , Chapter 16, Problem 16.23P , additional homework tip  17

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

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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,

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , Chapter 16, Problem 16.23P , additional homework tip  19

Mechanism:

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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.

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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,

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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,

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , Chapter 16, Problem 16.23P , additional homework tip  23

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

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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,

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , Chapter 16, Problem 16.23P , additional homework tip  25

Mechanism:

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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.

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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,

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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,

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , Chapter 16, Problem 16.23P , additional homework tip  29

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

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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,

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , Chapter 16, Problem 16.23P , additional homework tip  31

Mechanism:

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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.

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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,

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , 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,

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , Chapter 16, Problem 16.23P , additional homework tip  35

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

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , Chapter 16, Problem 16.23P , additional homework tip  36

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Chapter 16 Solutions

EP ORGANIC CHEMISTRY-OWL V2 ACCESS

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
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