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Chapter 12: PROBLEM 12.29 (page 487)

Question: Draw the products formed when A is treated with each reagent: (a) H2 Pd-C; (b) mCPBA; (c) PCC; (d) CrO3, H2SO4, H2O; (e) Sharpless reagent with (+)-DET.


Short Answer

Expert verified

Answer

a.

b.

c.

d.

e.

Step by step solution

01

Reduction reaction

Alkenes can be reduced to alkanes using the given reagent.The reaction is shown below:

Reduction of alkene

02

Oxidation reactions

Several reagents can be used to oxidize an alcoholic compound to ketone, aldehyde, carboxylic acid, and epoxide. Some of the reagents are PCC, .

The reactions are listed below:

Oxidation reactions

03

Epoxidation reactions

Epoxidation using mCPBA

The conversion of alkenes into epoxide using the reagent mCPBA leads to the syn addition of oxygen. The reaction is stereospecific in nature.

Epoxidation with mCPBA

  • Sharpless epoxidation

The conversion of allylic alcohols to epoxides using Sharpless reagents

Sharpless epoxidation

04

Reactions of the given compound

The given compound can be expressed in its skeletal structure as follows:

Skeletal structure of the compound

a.

Reduction reaction

b.

Epoxidation with mCPBA

c.

Oxidation with PCC

d.

Oxidation with Cr2O3 ,H2SO4,H2O

e.

Sharpless epoxidation with (+)-DET

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Most popular questions from this chapter

Question: Draw all alkenes that react with one equivalent of H2 in the presence of a palladium catalyst to form each alkane. Consider constitutional isomers only

a.

b.

c.

Question: Draw the organic products formed in each reaction.

a.

b.

c.

d.

Question: Identify the starting material in each reaction.

a.

b.

Question: For alkenes A, B, and C:

Compound A (Monosubstituted)

Compound B (Tetrasubstituted)

Compound C (disubstituted)

(a) Rank A, B, and C in order of increasing heat of hydrogenation;

(b) Rank A, B, and C in order of increasing rate of reaction with H2 Pd-C; (c) Draw the productsformed when each alkene is treated with ozone, followed by Zn-H2O.

Question: Which alkene in each pair has the larger Heat of hydrogenation?

a.

b.
See all solutions

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