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.

PROBLEM 12.29 - Organic Chemistry

PROBLEM 12.29

Question

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.

Step-by-Step Solution

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Answer

1Reduction reaction

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

Reduction of alkene

2Oxidation 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

3Epoxidation 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

4Reactions of the given compound

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

Skeletal structure of the compound

Reduction reaction

Epoxidation with mCPBA

Oxidation with PCC

Oxidation with Cr₂O_{3 ,}H₂SO_4,H₂O

Sharpless epoxidation with (+)-DET

PROBLEM 12.28

PROBLEM 12.30

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