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Chapter 11: Q66P (page 591)

Under normal circumstances, tertiary alcohols are not oxidized. However, when the tertiary alcohol is allylic, it can undergo a migration of the double bond (called an allylic shift) and subsequent oxidation of the alcohol. A particularly effective reagent for this reaction is Bobbitt鈥檚 reagent, similar to TEMPO used in many oxidations. (M. Shibuya et al., J. Org. Chem., 2008, 73, 4750.)

Show the expected product when each of these 3掳 allylic alcohols is oxidized by Bobbitt鈥檚 reagent.

(a)

(b)

(c)

(d)

Short Answer

Expert verified

The organic reagent that bears nitrogen and ketone groups and exists in salt form is Bobbitt鈥檚 reagent.

This compound is invented by James M. Bobbitt. This reagent is used for the preparation of alkaloids namely salsoline, carnegine, salsolidine, and lophocerine.

Step by step solution

01

About Bobbitt’s reagent

The organic reagent that bears nitrogen and ketone groups and exists in salt form is Bobbitt鈥檚 reagent.

This compound is invented by James M. Bobbitt. This reagent is used for the preparation of alkaloids namely salsoline, carnegine, salsolidine, and lophocerine.

02

Reaction of the first compound with Bobbitt’s reagent

A carbonyl group will be generated in the ring, and the double bond shift takes place. The OH group will be removed and the reaction is shown below.

03

Reaction of the second compound with Bobbitt’s reagent

A carbonyl group will be generated and the double bond shift takes place. The OH group will be removed and the reaction is shown below.

04

Reaction of the third compound with Bobbitt’s reagent

There will be the generation of a carbonyl group and the double bond shift takes place. The OH group will be removed. The reaction is shown below.

05

Reaction of the fourth compound with Bobbitt’s reagent

A carbonyl group will be generated and a double bond shift takes place. The OH group will be removed and the reaction is shown below.

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Most popular questions from this chapter

Some alcohols undergo rearrangement or other unwanted side reactions when they dehydrate in acid. Alcohols may be dehydrated under mildly basic conditions using phosphorus oxy-chloride (POCl3) in pyridine. The alcohol reacts with phosphorus oxychlorides much like it reacts with tosyl chloride (Section 11-5), displacing a chloride ion from phosphorus to give an alkyl dichlorophosphate ester. The dichlorophosphate group is an outstanding leaving group. Pyridine reacts as a base with the dichlorophosphate ester to give an E2 elimination. Propose a mechanism for the dehydration of cyclohexanol by POCl3 in pyridine.

The compound shown below has three different types of OH groups, all with different acidities. Show the structure produced after this compound is treated with different amounts of NaH followed by a methylating reagent. Add a brief explanation.

(a)1 equivalent of NaH, followed by 1 equivalent of CH3l and heat

(b)2 equivalents of NaH, followed by 2 equivalents of CH3l and heat

(c) 3 equivalents of NaH, followed by 3 equivalents of CH3l and heat

When 1-cyclohexylethanol is treated with concentrated aqueous, the major product is 1-bromo-1-ethylcyclohexane.

(a)Propose a mechanism for this reaction.

(b) How would you convert 1-cyclohexylethanol to (1-bromoethyl)cyclohexane in good yield?

Show how you would convert (S)-heptan-2-ol to

(a) (S)-2-chloroheptane.

(b) (R)-2-bromoheptane.

(c) (R)-heptan-2-ol.

Two products are observed in the following reaction.

(a) Suggest a mechanism to explain how these two products are formed.

(b) Your mechanism for part (a) should be different from the usual mechanism of the reaction of SOCl2 with alcohols. Explain why the reaction follows a different mechanism in

this case.
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