BuyFindarrow_forward

Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485

Solutions

Chapter
Section
BuyFindarrow_forward

Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485
Chapter 11.SE, Problem 41AP
Textbook Problem
30 views

Which compound in each of the following pairs will react faster in an SN2 reaction with OH-?

(a) CH3Br or CH3I

(b) CH3CH2I in ethanol or in dimethyl sulfoxide

(c) (CH3)3CCl or CH3Cl

(d) H2C=CHBr or H2C=CHCH2Br

Interpretation Introduction

Interpretation:

The faster reactant is to be identified from SN2 reaction with OH-.

Concept introduction:

SN2 reaction:

Tosylated compound is reaction with sodium methoxide which undergoes again SN2 type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,

Organic Chemistry, Chapter 11.SE, Problem 41AP

Given information:

a.

The given compound is shown below,

CH3I and CH3Br

b.

The given compound is shown below,

CH3CH2I in ethanol and CH3CH2I in dim ethylsulf oxide (DMSO)

c.

The given compound is shown below,

(CH3)3CCl and CH3Cl

d.

The given compound is shown below,

CH2 = CH2 Br or CH2 = CHCH2Br

Explanation of Solution

a.

The given compound is shown below,

CH3I and CH3Br

Methyl iodide is undergoing SN2 very faster because, iodine is good leaving group than bromine.

b.

The given compound is shown below,

CH3CH2I in ethanol and CH3CH2I in dim ethylsulfoxide (DMSO)

ethyl iodide in dimethyl sulfoxide is undergoes SN2 very faster than ethyl iodide in ethanol because hydroxide ion may form hydrogen bonding with protic solvent ethanol. Therefore, the reaction is slow.

c...

Still sussing out bartleby?

Check out a sample textbook solution.

See a sample solution

The Solution to Your Study Problems

Bartleby provides explanations to thousands of textbook problems written by our experts, many with advanced degrees!

Get Started

Chapter 11 Solutions

Organic Chemistry
Show all chapter solutions
add
Ch. 11.5 - Rank the following substances in order of their...Ch. 11.5 - 3-Bromo-1-butene and 1-bromo-2-butene undergo SN1...Ch. 11.5 - Predict whether each of the following substitution...Ch. 11.6 - Review the mechanism of geraniol biosynthesis...Ch. 11.7 - Ignoring double-bond stereochemistry, what...Ch. 11.7 - What alkyl halides might the following alkenes...Ch. 11.8 - What stereochemistry do you expect for the alkene...Ch. 11.8 - What stereochemistry do you expect for the...Ch. 11.9 - Which isomer would you expect to undergo E2...Ch. 11.12 - Tell whether each of the following reactions is...Ch. 11.SE - Write the product you would expect from reaction...Ch. 11.SE - From what alkyl bromide was the following alkyl...Ch. 11.SE - Assign R or S configuration to the following...Ch. 11.SE - Draw the structure and assign Z or E...Ch. 11.SE - Predict the product(s) and show the mechanism for...Ch. 11.SE - Show the mechanism for each reaction below. What...Ch. 11.SE - Predict the product(s) for each elimination...Ch. 11.SE - Predict the product(s) for each elimination...Ch. 11.SE - Predict the product(s) for each elimination...Ch. 11.SE - Predict the product of each reaction below and...Ch. 11.SE - We saw in Section 8-7 that bromohydrins are...Ch. 11.SE - The following tertiary alkyl bromide does not...Ch. 11.SE - Metabolism of S-adenosylhomocysteine (Section...Ch. 11.SE - Reaction of iodoethane with CN- yields a small...Ch. 11.SE - One step in the urea cycle for ridding the body of...Ch. 11.SE - Methyl esters (RCO2CH3) undergo a cleavage...Ch. 11.SE - SN2 reactions take place with inversion of...Ch. 11.SE - Propose a mechanism for the following reaction, an...Ch. 11.SE - Draw all isomers of C4H9Br, name them, and arrange...Ch. 11.SE - The following Walden cycle has been carried out....Ch. 11.SE - Which compound in each of the following pairs will...Ch. 11.SE - Which reactant in each of the following pairs is...Ch. 11.SE - What effect would you expect the following changes...Ch. 11.SE - What effect would you expect the following changes...Ch. 11.SE - How might you prepare each of the following...Ch. 11.SE - Which reaction in each of the following pairs...Ch. 11.SE - Predict the product and give the stereochemistry...Ch. 11.SE - (R)-2-Bromooctane undergoes racemization to give...Ch. 11.SE - Propose structures for compounds that fit the...Ch. 11.SE - What products would you expect from the reaction...Ch. 11.SE - 1-Chloro-1, 2-diphenylethane can undergo E2...Ch. 11.SE - Predict the major alkene product of the following...Ch. 11.SE - There are eight diastereomers of 1, 2, 3, 4, 5,...Ch. 11.SE - The reactions shown below are unlikely to occur as...Ch. 11.SE - Arrange the carbocations below, in order of...Ch. 11.SE - Order each of the following sets of compounds with...Ch. 11.SE - Order each of the following sets of compounds with...Ch. 11.SE - Predict the major product(s) of each reaction...Ch. 11.SE - Reaction of the following S tosylate with cyanide...Ch. 11.SE - Ethers can often be prepared by SN2 reaction of...Ch. 11.SE - Show the stereochemistry of the epoxide (see...Ch. 11.SE - In light of your answer to Problem 11-31, what...Ch. 11.SE - In addition to not undergoing substitution...Ch. 11.SE - The tosylate of (2R, 3S)-3-phenyl-2-butanol...Ch. 11.SE - In light of your answer to Problem 11-64, which...Ch. 11.SE - How can you explain the fact that...Ch. 11.SE - Predict the product(s) of the following reaction,...Ch. 11.SE - Alkynes can be made by dehydrohalogenation of...Ch. 11.SE - Based on your answer to Problem 11-68, predict the...Ch. 11.SE - (S)-2-Butanol slowly racemizes on standing in...Ch. 11.SE - Reaction of HBr with (R)-3-methyl-3-hexanol leads...Ch. 11.SE - Treatment of 1-bromo-2-deuterio-2-phenylethane...Ch. 11.SE - Propose a structure for an alkyl halide that gives...Ch. 11.SE - Although anti periplanar geometry is preferred for...Ch. 11.SE - In light of your answer to Problem 11-74, explain...Ch. 11.SE - The reaction of 1-chlorooctane with CH3CO2- to...Ch. 11.SE - Compound X is optically inactive and has the...Ch. 11.SE - When a primary alcohol is treated with...Ch. 11.SE - The amino acid methionine is formed by a...Ch. 11.SE - Amines are converted into alkenes by a two-step...Ch. 11.SE - The antipsychotic drug flupentixol is prepared by...

Additional Science Textbook Solutions

Find more solutions based on key concepts
Show solutions add
For safety, a person seeking medical help should inform their physician about use of herbs or other alternative...

Nutrition: Concepts and Controversies - Standalone book (MindTap Course List)

As a person moves about in a dry environment, electric charge accumulates on the person's body. Once it is at h...

Physics for Scientists and Engineers, Technology Update (No access codes included)

What is a meteorological tide?

Oceanography: An Invitation To Marine Science, Loose-leaf Versin