Show how you would synthesize the following compounds from any starting materials containing no more than six carbon atoms.

a)

b)

c)

Short Answer

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a)

b)

c)

Step by step solution

01

Grignard reaction

Grignard reaction occurs between the Grignard reagent and carbonyl-containing compounds like aldehydes, ketones, or epoxides. After hydrolysis results in forming 1°,2° , and 3° alcohols with new C-C bonds. The obtained alcohol on heating with sulfuric acid gives alkene products.

02

 Step 2: Synthesis of octan-3-ol

a) The target compound contains 11 carbon atoms, so the logical disconnections are two compounds containing one six-carbon fragment and one five-carbon fragment. These two compounds can be joined by using the Grignard reaction. The tetrasubstituted C=C is obtained by dehydration of3° alcohol, obtained by two routes of Grignard reaction.


Synthesis of compound a

03

Synthesis of octan-1-ol

b) The target compound contains 12 carbon atoms, so the logical disconnections are two compounds containing six carbon fragments. Starting compound, we take Grignard reagent and aldehyde, and after hydrolysis, we get alcohol. This alcohol is heated by using H2SO4to get an alkene, and on reaction with mCPBA, compound with oxirane ring is obtained. The best way to get epoxide rings is from double bonds, and from alcohols, we get double bonds.


Synthesis of compound b

04

 Step 4: Synthesis of 1-cyclohexylethanol

C) The target compound contains 14 carbon atoms, so the logical disconnections are two compounds containing six carbon fragments. Starting compound, we take Grignard reagent and ketone, and after that, by using Williamson ether synthesis, the ethyl group is put at the end to obtain the target compound.


Synthesis of compound c

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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

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.

Show how you would synthesize each tertiary alcohol by adding an appropriate Grignard reagent to a ketone.

(a)3-phenylhexane-3-ol (3ways)

(b) Ph3 COH

(c) 1-ethylcyclopentanol

(d) 2-cyclopentylpentan-2-ol

A formate ester, such as ethyl formate, reacts with an excess of a Grignard reagent to give (after protonation) secondary alcohols with two identical alkyl groups.

a. Propose a mechanism to show how the reaction of ethyl formate with an excess of allylmagnesium bromide gives, after protonation, hepta-1,6-dien-4-ol.


b. Show how you would use reactions of Grignard reagents with ethyl formate to synthesize the following secondary alcohols.

i. pentan-3-ol

ii. diphenylmethanol

iii. trans, trans-nona-2,7-dien-5-ol

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