Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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![**Question:**
What is the major product from the following reaction?
**Reaction Details:**
- Reactant: A terminal alkyne (3-methyl-1-butyne)
- Reagents:
1) A borane reagent (B is bonded with two hydrogens and a cyclohexane-like structure)
2) Hydrogen peroxide (H₂O₂) and sodium hydroxide (NaOH)
**Options for Major Product:**
- Option A: A terminal alkene with a hydroxyl group
- Option B: An aldehyde
- Option C: An internal alkene with a hydroxyl group
- Option D: A saturated alcohol
**Explanation of the Reaction:**
The reaction involves hydroboration-oxidation of a terminal alkyne. The borane reagent is used first, which adds across the alkyne triple bond in a syn addition manner, forming a boron intermediate. In the second step, hydrogen peroxide and sodium hydroxide oxidize this intermediate, replacing the boron group with a hydroxyl group, resulting in an alcohol. For terminal alkynes, however, this usually leads to an aldehyde product after tautomerization.
In this case, the reaction most likely leads to the formation of an aldehyde (Option B), due to the rearrangement following the oxidation step.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F28000c02-e2c6-4a8b-b2f9-904011bfd87b%2Fa84842cb-1697-46b3-99f3-cf63f148f816%2Fzee2pg8_processed.png&w=3840&q=75)
Transcribed Image Text:**Question:**
What is the major product from the following reaction?
**Reaction Details:**
- Reactant: A terminal alkyne (3-methyl-1-butyne)
- Reagents:
1) A borane reagent (B is bonded with two hydrogens and a cyclohexane-like structure)
2) Hydrogen peroxide (H₂O₂) and sodium hydroxide (NaOH)
**Options for Major Product:**
- Option A: A terminal alkene with a hydroxyl group
- Option B: An aldehyde
- Option C: An internal alkene with a hydroxyl group
- Option D: A saturated alcohol
**Explanation of the Reaction:**
The reaction involves hydroboration-oxidation of a terminal alkyne. The borane reagent is used first, which adds across the alkyne triple bond in a syn addition manner, forming a boron intermediate. In the second step, hydrogen peroxide and sodium hydroxide oxidize this intermediate, replacing the boron group with a hydroxyl group, resulting in an alcohol. For terminal alkynes, however, this usually leads to an aldehyde product after tautomerization.
In this case, the reaction most likely leads to the formation of an aldehyde (Option B), due to the rearrangement following the oxidation step.
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