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Chapter 10: Q57P (page 540)

Show how this 1° alcohol can be made from the following:

(a) a 1° alkyl bromide

(b) formaldehyde

(c) a 7-carbon aldehyde

(d) a carboxylic acid

(e) an alkene

(f) ethylene oxide

Short Answer

Expert verified

Primary alcohol can be easily prepared by the reaction of formaldehyde with the Grignard reagent. It is alcohol in which the hydroxy group is bonded to primary carbon atoms.

Step by step solution

01

Primary alcohol

Primary alcohol can be easily prepared by the reaction of formaldehyde with the Grignard reagent. It is alcohol in which the hydroxy group is bonded to primary carbon atoms.

02

Formation of desired product

(a) Treatment of (2-bromoethyl) cyclopentane with aqueous KOH gives the desired compound. The reaction is as follows:


Formation of product in reaction a

b) Treatment of formaldehyde with (cyclopentyl methyl) magnesium bromide followed by hydrolysis gives the desired compound. The reaction is as follows:

Formation of product in reaction b

c) Treatment of 2-cyclopentylacetaldehyde with lithium aluminum hydride followed by hydrolysis gives the desired compound. The reaction is as follows:

Formation of product in reaction c

d) Treatment of 2-cyclopentylacetic acid with lithium aluminum hydride followed by hydrolysis gives the desired compound. The reaction is as follows:

e) The hydroboration of vinylcyclopentane followed by oxidation gives the desired compound. The reaction is as follows:


Formation of product in reaction e

f) Treatment of cyclopentylmagnesium bromide with oxirane followed by hydrolysis give the desired compound. The reaction is as follows:


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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

Propose structures for intermediates and products (A) through (K).

In Section 9-7B, we saw how acetylide ions add to carbonyl groups in much the same way as Grignard and organolithium reagents. Acetylide ions also add to ethylene oxide much like Grignard and organolithium reagents. Predict the products obtained by adding the following acetylide ions to ethylene oxide, followed by a dilute acid workup.

a.

b.

Predict the products you would expect from the reaction of NaBH4 with the following compounds. You may assume that these reactions take place in methanol as the solvent

a.CH3(CH2)8-CHO

b.

c. Ph-COOH

d.

e.

f.

Complete the following acid-base reactions. In each case, indicate whether the equilibrium favors the reactants or the products, and explain your reasoning.

a)

b)

c)

d)

e) (CH3)3 C-O- + CH3CH2OH⇄

f)(CH3)3 C-O- + H2O ⇄

g) KOH+ CH3CH2OH ⇄

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