Solution Found!
Develop syntheses for the following compounds, using
Chapter 21, Problem 25P(choose chapter or problem)
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.