cyclopentanol ----> cyclopentanone
Which of the following sets of reagents could be used to accomplish the above transformation?
a)CrO3/H2SO4
b)KMnO4/H2O
c)71% HNO3 @ 10-20 degrees Celcius
d)all of the above
To determine which set of reagents can be used to convert cyclopentanol to cyclopentanone, we need to consider the type of reaction involved.
The conversion of an alcohol to a ketone typically involves oxidation, where the alcohol is transformed into a carbonyl group. Let's evaluate each set of reagents and see if they are capable of oxidizing cyclopentanol to cyclopentanone:
a) CrO3/H2SO4:
This is known as the Jones oxidation, and it is commonly used to convert primary and secondary alcohols to their corresponding carbonyl compounds. However, cyclopentanol is a tertiary alcohol, which means it does not have any hydrogen atoms bonded to the carbon bearing the hydroxyl group. As a result, it cannot be oxidized by the CrO3/H2SO4 reagents. Therefore, option (a) is not suitable for this transformation.
b) KMnO4/H2O:
This reagent, also known as potassium permanganate, is a strong oxidizing agent. It can oxidize primary and secondary alcohols to carbonyl compounds. However, like in option (a), cyclopentanol is a tertiary alcohol and cannot undergo oxidation with KMnO4/H2O. Therefore, option (b) is also not applicable.
c) 71% HNO3 @ 10-20 degrees Celsius:
Nitric acid (HNO3) is a strong oxidizing agent and can potentially oxidize primary, secondary, and tertiary alcohols. However, the reaction conditions mentioned (71% HNO3 at 10-20 degrees Celsius) suggest a mild condition. Generally, such mild conditions are not sufficient to oxidize tertiary alcohols. Hence, option (c) is unlikely to work.
d) None of the above options:
Given that none of the provided sets of reagents are suitable for the oxidation of cyclopentanol to cyclopentanone, the correct answer is "None of the above" (d).
To achieve this transformation, alternative reagents or methods that are specifically suited for tertiary alcohols, like cyclopentanol, would need to be considered. One such example is the Swern oxidation, which uses the combination of dimethyl sulfoxide (DMSO) and oxalyl chloride (COCl)2.