The major product in the reaction CH3CH2C≡CH→THFBD3→CH3COOHProduct.Product is

The major product is 1-butene with deuterium at C-2, written as CH2=CD–CH2–CH3. BD3 in THF is borane where the hydrogens are deuterium (D). It performs hydroboration of an alkyne with syn addition and anti-Markovnikov regiochemistry.CH3COOH (acetic acid) then carries out protonolysis, replacing the vinyl–boron bond by hydrogen (H) without changing the C=C position. Step-by-step mechanism summary Starting alkyne: 1-butyne, CH3CH2C≡CH.Hydroboration with BD3 adds B to the less substituted carbon (the terminal carbon) and adds D to the internal carbon, syn across the triple bond, giving a vinyl borane: CH3CH2C(D)=CH–B.Protonolysis with CH3COOH replaces the vinyl–B by H while keeping the double bond. The result is a terminal alkene.Resulting structure and labelingThe double bond ends up between C-1 and C-2, so the product is 1-butene. Deuterium came from BD3 and sits on C-2, while hydrogen from acetic acid sits on C-1. Final product: CH2=CD–CH2–CH3 (1-butene-2-d).

The major product in the reaction CH3CH2C≡CH→THFBD3→CH3COOHProduct.Product is

The major product is 1-butene with deuterium at C-2, written as CH2=CD–CH2–CH3. BD3 in THF is borane where the hydrogens are deuterium (D). It performs hydroboration of an alkyne with syn addition and anti-Markovnikov regiochemistry.CH3COOH (acetic acid) then carries out protonolysis, replacing the vinyl–boron bond by hydrogen (H) without changing the C=C position. Step-by-step mechanism summary Starting alkyne: 1-butyne, CH3CH2C≡CH.Hydroboration with BD3 adds B to the less substituted carbon (the terminal carbon) and adds D to the internal carbon, syn across the triple bond, giving a vinyl borane: CH3CH2C(D)=CH–B.Protonolysis with CH3COOH replaces the vinyl–B by H while keeping the double bond. The result is a terminal alkene.Resulting structure and labelingThe double bond ends up between C-1 and C-2, so the product is 1-butene. Deuterium came from BD3 and sits on C-2, while hydrogen from acetic acid sits on C-1. Final product: CH2=CD–CH2–CH3 (1-butene-2-d).

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The major product in the reaction CH₃CH₂C $\equiv$ CH $\to_{THF}^{{BD}_{3}}$ $\overset{{CH}_{3} COOH}{\to}$ Product.Product is

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Detailed Solution

The major product is 1-butene with deuterium at C-2, written as CH₂=CD–CH₂–CH₃.

BD₃ in THF is borane where the hydrogens are deuterium (D). It performs hydroboration of an alkyne with syn addition and anti-Markovnikov regiochemistry.
CH₃COOH (acetic acid) then carries out protonolysis, replacing the vinyl–boron bond by hydrogen (H) without changing the C=C position.

Step-by-step mechanism summary

Starting alkyne: 1-butyne, CH₃CH₂C≡CH.
Hydroboration with BD₃ adds B to the less substituted carbon (the terminal carbon) and adds D to the internal carbon, syn across the triple bond, giving a vinyl borane: CH₃CH₂C(D)=CH–B.
Protonolysis with CH₃COOH replaces the vinyl–B by H while keeping the double bond. The result is a terminal alkene.

Resulting structure and labeling

The double bond ends up between C-1 and C-2, so the product is 1-butene. Deuterium came from BD₃ and sits on C-2, while hydrogen from acetic acid sits on C-1. Final product: CH₂=CD–CH₂–CH₃ (1-butene-2-d).

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