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Chapter 12: PROBLEM 12.44 (page 489)

Question: What alkene is needed to synthesize each 1,2-diol using [1] followed by NAHSO3 in H2O ; or [2] CH3CO3H followed by -OH in H2O ?

a.

b.

c.

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

Reaction of an alkene with osmium tetroxide

The reaction of an alkene with osmium tetroxide yields glycols.

The addition of hydroxyl group to an alkene follows syn addition (addition of substituents on the same face).

02

Reaction of an alkene with peracids

The reaction of an alkene with peracids, followed by a reaction with a base, yields a glycol.

The addition of a hydroxyl group to an alkene follows anti addition (addition of substituents on different faces).

The reaction proceeds through the formation of an epoxide.

03

Synthesis of a

Compound a can be synthesized as shown:

Synthesis of a

04

Synthesis of b

Compound b can be synthesized as shown:

Synthesis of b

05

Synthesis of c

Compound c can be synthesized as shown:

Synthesis of c

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Most popular questions from this chapter

Question: Sodium hypochlorite (NaOCl, the oxidant in household bleach) in aqueous CH3COOH is also touted as a “green” oxidizing agent. For example, oxidation of (CH3)2CHOH with NaOCl forms along with NaCl and H2O. (a) What advantages and/or disadvantages does this method have over oxidation with HCrO4––Amberlyst A-26 resin? (b) What advantages and/or disadvantages does this method have over oxidation with CrO3, H2SO4,H2O.

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.

Question: Epoxidation of the following allylic alcohol using the Sharpess reagent (-)-DET gives two epoxy alcohols in a ratio of 87:13.

  1. Assign structures to the major and minor product.
  2. What is the enantiomeric excess in this reaction?

Question: What carbonyl compound is formed when each alcohol is treated with HCrO4––Amberlyst A-26 resin?

a.

b.

c.

Question: In the Cr6+oxidation of cyclohexanols, it is generally true that sterically hindered alcohols react faster than unhindered alcohols. Which of the following alcohols should be oxidized more rapidly?
See all solutions

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