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15240672380's Question
Chemistry
Posted 10 months ago

Draw the organic product of the following reaction.
- You do not have to consider stereochemistry.
- You do not have to explicitly draw H\mathrm{H} atoms.
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Answer from Sia
Posted 10 months ago
Solution
1
Identify the starting material: The organic compound described is 1-butyne, which has the structure CH3CCCH3CH_3C\equiv CCH_3
2
First reaction step with NaNH2: Sodium amide, NaNH2, is a strong base that will deprotonate the terminal alkyne, creating a sodium acetylide anion. The reaction is CH3CCCH3+NaNH2CH3CCNa++NH3CH_3C\equiv CCH_3 + NaNH_2 \rightarrow CH_3C\equiv C^-Na^+ + NH_3
3
Second reaction step with CH3CH2Br: The sodium acetylide anion will act as a nucleophile and attack the primary alkyl halide, bromoethane, in an SN2 reaction, displacing the bromide ion and forming a new carbon-carbon bond. The reaction is CH3CCNa++CH3CH2BrCH3CCCH2CH3+NaBrCH_3C\equiv C^-Na^+ + CH_3CH_2Br \rightarrow CH_3C\equiv CCH_2CH_3 + NaBr
Answer
The organic product of the following reaction is pent-1-yne, CH3CCCH2CH3CH_3C\equiv CCH_2CH_3.
Key Concept
Alkyne deprotonation and subsequent nucleophilic substitution
Explanation
A terminal alkyne is deprotonated by a strong base to form an acetylide anion, which then acts as a nucleophile in an SN2 reaction with a primary alkyl halide to form a new carbon-carbon bond.

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