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Q39.

Expert-verified
Organic Chemistry
Found in: Page 376

Short Answer

Question: Draw the product and indicate the stereochemistry when the given alcohol is treated with each reagent: (a) HBr; (b) ;(c) HCl ;(d)and pyridine.

Answer

a.

b.

c.

d.

See the step by step solution

Step by Step Solution

Step-by-Step SolutionStep 1: Treatment of alcohol with HCl and HBr

The alcohols can combine with HX like HCl and HBr leading to the formation of alkyl halides.

Step 2: Treatment of alcohol with  PBr3

The reaction of 1° ,2°and 3° with leads to the formation of alkyl bromides. The by-product produced in the reaction is .

Step 3: Treatment of alcohol with

The reaction of 1° ,2° ,3° with and pyridine leads to the formation of alkyl chlorides. The by-products obtained in this reaction are and HCl.

Step 4: Product and stereochemistry when the alcohol is treated with each reagent

The skeletal structure of the compound is given below:

Skeletal structure of the given alcohol

The structure with the stereogenic center is given below:

Structure of the given alcohol with stereogenic center

a. The given reaction results in the formation of a racemic mixture. The reaction of HBr with the given alcohol is shown below:

The reaction of the given alcohol with HBr

b. The reaction leads to the product formation with an inversion of configuration. The product formed by the reaction of alcohol with is given below:

The reaction of the given alcohol with

c. The given reaction is an reaction, and the final product exhibits an inversion of configuration. The reaction of the given alcohol with HCl is given below:

The reaction of the given alcohol with HCl

d. The reaction follows an path, and the product obtained in the reaction exhibits an inversion in configuration. The reaction of the alcohol with and pyridine is given below:

The reaction of the given alcohol with and pyridine

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