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Chapter 12: PROBLEM 12.16 (page 470)

Question: Draw all stereoisomers formed when each alkene is treated with mCPBA.

a.

b.

c.

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

Epoxidation of alkene

The epoxidation of alkene is the addition of one oxygen to an alkene by forming two new C-O bonds. Epoxidation is carried out using peroxyacid, e.g., meta-Chloroperoxybenzoic acid (mCPBA)

02

Stereochemistry of epoxidation

The addition of oxygen to an alkene is syn (addition from the same side). Therefore, reactions are stereospecific.

Cis alkene epoxidation results in cis epoxide and trans alkene results in trans epoxide.

03

Reaction when alkene is treated with mCPBA

Since oxygen can be added from above as well as below the plane, two products are obtained.

When the reactant is cis, the two products obtained are diastereomers (identical or meso products)

When the reactant is trans, the two products obtained are enantiomers (non-identical and non-superimposable mirror images). The product thus is a racemic mixture.

a.

Trans reactant - enantiomeric product (racemic mixture)

b.

Cis reactant - diastereomers

c.

Trans reactant - enantiomers

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Most popular questions from this chapter

Question: Draw the products formed when each alkene is treated with O3 followed by Zn, H2O.

a.

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Question: Draw the organic products formed when allylic alcohol A is treated with each reagent.

a. H2 +Pd-c

b. mCPBA

c. PCC

d. CrO3 ,H2SO4, H2O

e.(CH3)3COOH , Ti [OCH(CH3)3]4 (+) -DET

f.(CH3)3COOH , Ti [OCH(CH3)3]4 (-) -DET

g. [1] PBr3,[2] LiAlH4 ,[3] H2O

h. HCrO4- 鈥揂mberlyst A-26 resin

Question: What alkyne (or diyne) yields each set of oxidative cleavage products?

a.

b.

c.

d.

Question: Devise a synthesis of each compound from CH3CH2OHas the only organic starting material; that is, every carbon in the product must come from a molecule of ethanol. You may use any other needed inorganic reagents.

Question: Draw the organic products in each of the following reactions.

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c.

d.
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