Essential Organic Chemistry (3rd Edition)
Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
bartleby

Concept explainers

Question
Book Icon
Chapter 20, Problem 17P

(a)

Interpretation Introduction

Interpretation:

The product formed when cholesterol reacts with hydrogen in presence of palladium-carbon has to be drawn.

(a)

Expert Solution
Check Mark

Explanation of Solution

Cholesterol with hydrogen:

Essential Organic Chemistry (3rd Edition), Chapter 20, Problem 17P , additional homework tip  1

Cholesterol reacts with hydrogen in presence of palladium-carbon to reduce double bond to single bond and forms cholestanol.  Therefore, the product obtained is cholestanol which is shown in the above scheme.

(b)

Interpretation Introduction

Interpretation:

The product formed when cholesterol reacts with acetyl chloride has to be drawn

(b)

Expert Solution
Check Mark

Explanation of Solution

Cholesterol with acetyl chloride:

Essential Organic Chemistry (3rd Edition), Chapter 20, Problem 17P , additional homework tip  2

Cholesterol reacts with acetyl chloride in which acetylation reaction take place at hydroxyl group and forms cholesteryl acetate.  Therefore, the product obtained is cholesteryl acetate which is shown in the above scheme.

(c)

Interpretation Introduction

Interpretation:

The product formed when cholesterol reacts with sulfuric acid followed by heating has to be drawn.

(c)

Expert Solution
Check Mark

Explanation of Solution

Cholesterol with sulfuric acid:

Essential Organic Chemistry (3rd Edition), Chapter 20, Problem 17P , additional homework tip  3

Cholesterol reacts with sulfuric acid in which removal of water molecule take place and forms cholestene.  Therefore, the product obtained is cholestene which is shown in the above scheme.

(d)

Interpretation Introduction

Interpretation:

The product formed when cholesterol reacts with water in presence of acid has to be drawn.

(d)

Expert Solution
Check Mark

Explanation of Solution

Cholesterol with water:

Essential Organic Chemistry (3rd Edition), Chapter 20, Problem 17P , additional homework tip  4

Cholesterol reacts with water in presence of water in which removal of water molecule take place and forms desired product.  Therefore, the product obtained is is shown in the above scheme.

(e)

Interpretation Introduction

Interpretation:

The product formed when cholesterol reacts with peroxy acid has to be drawn

(e)

Expert Solution
Check Mark

Explanation of Solution

Cholesterol with peroxy acid:

Essential Organic Chemistry (3rd Edition), Chapter 20, Problem 17P , additional homework tip  5

Cholesterol reacts with peroxy acid in presence of water in which reaction take place at double bond and forms epoxide product.  Therefore, the epoxide product obtained is shown in the above scheme.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!
Students have asked these similar questions
Draw the product that is obtained from the reaction of cholesterol with the following reagents a. H2, Pd/C                  b. acetyl chloride                              c. H2SO4, ∆              d. H2O, H+                     e. a peroxyacid
How many products are obtained when the phospholipid below is saponified? a. 2 b. 6 c. 5 d. 3
Draw the product that is obtained from the reaction of cholesterol with the acetyl chloride
Knowledge Booster
Background pattern image
Chemistry
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.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Text book image
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Text book image
Pushing Electrons
Chemistry
ISBN:9781133951889
Author:Weeks, Daniel P.
Publisher:Cengage Learning