What is the major organic product of the fallowing reaction? 1) 9-BBN, THF 2) H2O2, KOH, H,O [9-BBN is a borane derivative that has only one reactive B-H bond. It reacts just like BH3-THF) ОН HO H. Но H.

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...
icon
Related questions
Question

This is a question from a study guide for o-chem.  If you can please go though the difference between a major and minor product and help me break down the reaction a bit id really appreciate it.

**Question:**

What is the major organic product of the following reaction?

**Reaction Conditions:**

1) 9-BBN, THF  
2) H₂O₂, KOH, H₂O

*[9-BBN is a borane derivative that has only one reactive B-H bond. It reacts just like BH₃•THF]*

**Reaction Scheme:**

A terminal alkyne is given, followed by an arrow indicating the application of the reaction conditions.

**Options for the Major Organic Product:**

1. **Structure 1:**
   - A ketone with phenyl and isopropyl groups.

2. **Structure 2:**
   - An alcohol with an internal double bond and hydroxyl groups on the alkene carbons.

3. **Structure 3:**
   - An alcohol with the hydroxyl group attached to the end carbon of the alkyne chain (tautomerization possible).

4. **Structure 4:**
   - A ketone with an isopropyl group and phenyl group directly attached to different carbons.

**Explanation of Graphs/Diagrams:**

- The reaction involves hydroboration-oxidation of the terminal alkyne. 9-BBN (9-borabicyclo[3.3.1]nonane) is used as the hydroboration reagent which adds across the triple bond.
- The subsequent oxidation step uses hydrogen peroxide in the presence of a base (KOH) to transform the boron into a hydroxyl group.
- The expected product is an anti-Markovnikov alcohol which may tautomerize to form an aldehyde or ketone under certain conditions.

For educational purposes, it's crucial to note that 9-BBN is selective and typically gives regioselective addition across unsaturated systems, resulting in the formation of alcohols from alkynes.
Transcribed Image Text:**Question:** What is the major organic product of the following reaction? **Reaction Conditions:** 1) 9-BBN, THF 2) H₂O₂, KOH, H₂O *[9-BBN is a borane derivative that has only one reactive B-H bond. It reacts just like BH₃•THF]* **Reaction Scheme:** A terminal alkyne is given, followed by an arrow indicating the application of the reaction conditions. **Options for the Major Organic Product:** 1. **Structure 1:** - A ketone with phenyl and isopropyl groups. 2. **Structure 2:** - An alcohol with an internal double bond and hydroxyl groups on the alkene carbons. 3. **Structure 3:** - An alcohol with the hydroxyl group attached to the end carbon of the alkyne chain (tautomerization possible). 4. **Structure 4:** - A ketone with an isopropyl group and phenyl group directly attached to different carbons. **Explanation of Graphs/Diagrams:** - The reaction involves hydroboration-oxidation of the terminal alkyne. 9-BBN (9-borabicyclo[3.3.1]nonane) is used as the hydroboration reagent which adds across the triple bond. - The subsequent oxidation step uses hydrogen peroxide in the presence of a base (KOH) to transform the boron into a hydroxyl group. - The expected product is an anti-Markovnikov alcohol which may tautomerize to form an aldehyde or ketone under certain conditions. For educational purposes, it's crucial to note that 9-BBN is selective and typically gives regioselective addition across unsaturated systems, resulting in the formation of alcohols from alkynes.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Alkanes and Cycloalkanes
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY