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Q50.

Expert-verified
Organic Chemistry
Found in: Page 377

Short Answer

Question: Draw the substitution product formed (including stereochemistry) when (R)-hexan-2-ol is treated with each series of reagents: (a) NaH, followed by ; (b) TsCl and pyridine, followed by ; (c) , followed by . Which two routes produce identical products?

Answer

a.

b.

c.

Route (a) and route (c) produces identical products.

See the step by step solution

Step by Step Solution

Step-by-Step SolutionStep 1: Reaction of alcohols

Alcohols can get subjected to nucleophilic substitution reactions or elimination reactions if the OH group is transformed into an excellent leaving group. This can be done with the help of acids.

Step 2: Stereochemistry

The spatial organization of various atoms can be investigated using stereochemistry. Chiral molecules can be analyzed using stereochemistry.

Step 3: Reaction of (R)-hexan-2-ol with various reagents

a. The reaction of (R)-hexan-2-ol with NaH and does not lead to a change in configuration and the reaction can be given as:

The reaction of (R)-hexan-2-ol with NaH and

b. The reaction of (R)-hexan-2-ol with TsCl and pyridine, followed by leads to a change in configuration and the reaction can be given as:

The reaction of (R)-hexan-2-ol with TsCl and pyridine, followed by

c. The reaction of (R)-hexan-2-ol with followed by does not lead to a change in configuration and the reaction can be given as:

The reaction of followed by

The products produced in reactions a and c are (R)-2-methoxyhexane. Hence, routes (a) and (c) produces identical products.

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