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Develop syntheses for the following compounds, using

Chapter 21, Problem 25P

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QUESTION:

Develop syntheses for the following compounds, using acetylene and compounds containing no more than four carbon atoms as your organic starting materials.

(a) 3-methylnon-4-yn-3-ol (“3-ol” means there is an OH group on C3.)

(b) cis-1-ethyl-2-methylcyclopropane

Equation Transcription:

Text Transcription:

OH

C3

CH_{3}CH_2

CH_{2}CH_{2}CH_3

Questions & Answers

QUESTION:

Develop syntheses for the following compounds, using acetylene and compounds containing no more than four carbon atoms as your organic starting materials.

(a) 3-methylnon-4-yn-3-ol (“3-ol” means there is an OH group on C3.)

(b) cis-1-ethyl-2-methylcyclopropane

Equation Transcription:

Text Transcription:

OH

C3

CH_{3}CH_2

CH_{2}CH_{2}CH_3

ANSWER:

Solution 25P

(a)

Starting with acetylene, treatment with sodium amide yields sodium acetylide. This is a strong nucleophile. Reaction with butyl bromide initiates an  reaction, placing the desired butyl group on one side of the alkyne. The remaining acetylene hydrogen can then be deprotonated to form another nucleophilic species. Reaction of this alkyne anion with a ketone (which has an electrophilic carbonyl carbon) followed by water quench yields the desired product.

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