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Chapter 10: Q14P (page 513)

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.

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

Secondary alcohols by Grignard reagents

Secondary alcohols ( alcohols) are formed when the Grignard reagent (with any of three halides- Cl, Br, I) is added to aldehydes except for formaldehyde.It takes place in the presence of a solvent (like ether), and the other step is the addition of H3O+ .

02

Formation of secondary alcohol in (a)

Grignard reagent ( CH3- CH2- CHCH3- CH2MgCl) and aldehyde ( CH3CHO) are used in the first method. In the second method, the alkyl groups of Grignard reagent and aldehyde are interchanged

03

Formation of secondary alcohol in (b)

b. Grignard reagent ( C6H5MgBr) and aldehyde ( CH3CH2CHO) are used in the first method. In the second method, the alkyl groups of Grignard reagent and aldehyde are interchanged.

Synthesis of secondary alcohol

04

Formation of secondary alcohol in (c)

c. Grignard reagent (CH2= CHCH2MgCl ) and aldehyde (C6H11CHO ) are used in the first method. In the second method, the alkyl groups of Grignard reagent and aldehyde are interchanged.

Synthesis of secondary alcohol

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Most popular questions from this chapter

Predict which member of each pair has the higher boiling point, and explain the reasons for your predictions.

(a) pentan-1-ol or 3-methylbutan-1-ol

(b) pentan-2-one or pentan-2-ol

(c) pentan-2-ol or pentane-1,5-diol

(d) pentan-2-ol or heptan-2-ol

Ever since the Grignard reaction was discovered to react with ethylene oxide, chemists have experimented with other epoxides to test the limits of this reaction (which chemists call the scope of the reaction). The conclusion is that the success of the Grignard reaction is limited by the steric hindrance in the epoxide. One group published results of several Grignard reagents on one epoxide; one of their products is shown here. What Grignard reagent and what epoxide were used to make this compound? Comment on the steric requirements of the epoxide and the stereochemistry of the product.

Predict which member of each pair is more acidic, and explain the reasons for your predictions.

(a) cyclohexanol or 3-chlorophenol

(b) cyclopentanol or cyclopentanethiol

(c) cyclopentanol or cyclopentanecarboxylic acid

(d) pentan-1-ol or 2,2-dichloropentan-1-ol

Show how you would add Grignard reagents to acid chlorides or esters to synthesize the following alcohols.

  1. Ph3C-OH
  2. 3-ethyl-2-methylpentan-3-ol
  3. dicyclohexylphenylmethanol

Geminal diols, or 1,1-diols, are usually unstable, spontaneously losing water to give carbonyl compounds. Therefore, germinal diols are regarded as hydrated forms of ketones and aldehydes. Propose a mechanism for the acid-catalyzed loss of water from propane-2,2-diol to give acetone.
See all solutions

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