Concept explainers
Show how each of the following compounds can be synthesized from cyclopentanol and any necessary organic or inorganic reagents. In many cases the desired compound can be made from one prepared in an earlier part of the problem.
trans-
Interpretation:
Each of the given product is to be synthesized from cyclopentanol and necessary organic or inorganic reagents.
Concept introduction:
Alcohols can be prepared from a variety of reagents.
Reaction of Grignard reagents with carbonyl compounds produces the corresponding alcohols.
Grignard reagents also react with oxiranes to produce alcohols.
The allylic and benzylic carbon atoms are selectively brominated using NBS reagent.
Alcohols undergo dehydration in acidic medium, producing alkenes. These alkenes can be converted to diols using osmium tetra oxide.
Answer to Problem 23P
Solution:
Explanation of Solution
Synthesis of
The structure for cyclopentanol and
In
Synthesis of
The structure for cyclopentanol and
In
The sequence of reactions starting from cyclopentanol to yield the final given product
Synthesis of
The structure for cyclopentanol and
In
The sequence of reactions starting from cyclopentanol to yield the final given product
Synthesis of
The structure for cyclopentanol and
In
The sequence of reactions starting from cyclopentanol to yield the final given product
Synthesis of the given diol from cyclopentanol.
The structure for the given diol is as follows:
In the given diol, one phenyl ring and one hydroxyl group are attached to the same carbon of cyclopentane ring. The other hydroxyl group is attached to C2 position of cyclopentane ring.
Oxidation of the cyclopentanol will produce cyclopentanone. Reaction of this cyclopentanone with phenyl magnesium bromide will form a tertiary alcohol. Acid catalyzed dehydration of this tertiary alcohol will produce
The sequence of reactions starting from cyclopentanol to yield the final given product
Synthesis of
The structure for cyclopentanol and
Cyclopentanol, when undergoes oxidation in presence of a mild oxidizing agent such as pyridinium chlorochromate in dichlormethane, the hydroxyl group turns to a carbonyl group and forms cyclopentanone. Cyclopentanone, when treated with Grignard reagent (PhMgBr) in the presence of diethyl ether with acidic workup, forms
The sequence of reactions is shown below.
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Chapter 16 Solutions
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