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Chapter 10: Q13P (page 516)

Question: Show how you would synthesize the following primary alcohols by adding an appropriate Grignard reagent to formaldehyde.

a.

b.

c.

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

Synthesis of alcohol

The primary alcohol is synthesized when the Grignard reagent is added to formaldehyde, but the secondary alcohol is formed when aldehyde other than formaldehyde is added to the Grignard reagent.These reactions take place in the presence of solvents like ether.

02

Synthesis of a primary alcohol in (a)

a. When Grignard reagent ( ) is added to formaldehyde (HCHO) in the presence of ether and the second step with , it results in the formation of primary alcohol.


Synthesis of primary alcohol

03

Synthesis of a primary alcohol in (b)

b. When Grignard reagent ( ) is added to formaldehyde (HCHO) in the presence of ether, and then with , it forms primary alcohol.


Synthesis of primary alcohol

04

Synthesis of primary alcohol in (c)

c. When Grignard reagent ( ) is added to formaldehyde (HCHO) in the presence of ether, and then with H3O+, it forms primary alcohol.


Synthesis of primary alcohol

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Most popular questions from this chapter

Show how to make these deuterium-labeled compounds, using CD3MgBrand D2Oas your sources of deuterium, and any non-deuterated starting materials you wish.

(a) CH3CH(OD)CD3(b) CH3C(OH)(CD3)2 (c) CD3CH2CH2O(d) Ph(CD3)2COD

Grignard reagents react slowly with oxetane to produce primary alcohols. Propose a mechanism for this reaction, and suggest why oxetane reacts with Grignard reagents even though most ethers do not.

Question: Show two ways you could synthesize each of the following secondary alcohols by adding an appropriate Grignard reagent to an aldehyde.

a.

b.

c.

Give both the IUPAC name and the common name for each alcohol.

(a) CH3CH(OH)CH3

(b)

(c)

(d)(CH3)2CHCH2OH

Show how you would accomplish the following transformations. You may use any additional reagents you need.

  1. octan-3-ol from hexanal, CH3 (CH 2)4CHO
  2. octan-1-ol from 1-bromoheptane
  3. 1-cyclohexylethanol from acetaldehyde, CH3CHO
  4. 1-cyclohexylethanol from bromocyclohexane
  5. benzylalcohol (ph-CH2-CHO)from bromobenzene (ph-Br)

g. cyclopentylphenylmethanol from benzaldehyde

h. octan-1-ol from 1-bromohexane
See all solutions

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