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Chapter 7: PROBLEM 7.39 (page 288)

Question: The ether CH3OCH2CH3can be prepared by two different nucleophilic substitution reactions, one using CH3O- as a nucleophile and the other using CH3CH2O- as a nucleophile. Draw both routes

Short Answer

Expert verified

ANSWER

Route when is used as a nucleophile

Route when is used as a nucleophile

Step by step solution

01

Nucleophiles

Nucleophiles are molecules containing lone pairs, a negative charge, or both.

02

Nucleophilic substitution reactions

In these reactions, the nucleophile attacks an electrophile by donating a pair of free electrons.

03

Different routes for the preparation of the given ether

When CH3O-is a nucleophile, the carbon framework of the required alkyl halide must be CH3CH2X (where X is halide ion). However, when CH3CH2O- is the nucleophile, the carbon framework of the required alkyl halide must be CH3X (where X is halide ion).

Hence, the desired reaction routes are shown below:

Route when is used as a nucleophile

Route when is used as a nucleophile

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Most popular questions from this chapter

Question: Determine the mechanism of nucleophilic substitution of each reaction and draw the products, including stereochemistry.

a.

b.

c.

d.

e.

f.

Question: Classify each solvent as protic or aprotic.

  1. (CH3)2CHOH
  2. CH3NO2
  3. CH2Cl2
  4. NH3
  5. N(CH3)3
  6. HCONH2

Question: Nicotine can be made when the following salt is treated with Na2Co3 . Draw a stepwise mechanism for this reaction.

Question: Give the IUPAC name for each compound, including any R,S designation.

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Question: Draw the products of each nucleophilic substitution reaction.


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c.

d.

e.

f.
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