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Chapter 10: Problem 75

Draw the product of treating each alcohol with \(\mathrm{PCC}\). (a) M-Mexanol (b) 2.Mexanol (c) Cyclohexanol

Short Answer

Expert verified
Answer: The products formed are (a) Formaldehyde, (b) 2-Methyl-2-propanone, and (c) Cyclohexanone.

Step by step solution

01

Draw the structure of M-Mexanol (example 1)

M-Mexanol is methanol, which has the formula CH3OH. Its structure is H-C-O-H
02

Treat M-Mexanol with PCC

Since M-Mexanol is a primary alcohol, it will be oxidized to an aldehyde. Upon treatment with PCC, the hydroxyl group (OH) will be replaced by a carbonyl group (C=O).
03

Draw the product for example 1

The product formed in example 1 is formaldehyde, which has the formula CH2O. Its structure is H-C=O.
04

Draw the structure of 2-Mexanol (example 2)

2-Mexanol is 2-methyl-2-propanol, which has the formula (CH3)3COH. Its structure is (CH3)3C-O-H.
05

Treat 2-Mexanol with PCC

Since 2-Mexanol is a secondary alcohol, it will be oxidized to a ketone. Upon treatment with PCC, the hydroxyl group (OH) will be replaced by a carbonyl group (C=O).
06

Draw the product for example 2

The product formed in example 2 is 2-methyl-2-propanone, which has the formula (CH3)3CO. Its structure is (CH3)3C=O.
07

Draw the structure of Cyclohexanol (example 3)

Cyclohexanol has the formula C6H11OH. Its structure is a six-membered ring with a hydroxyl (OH) group attached to one of the carbon atoms.
08

Treat Cyclohexanol with PCC

Since Cyclohexanol is a secondary alcohol, it will be oxidized to a ketone. Upon treatment with PCC, the hydroxyl group (OH) will be replaced by a carbonyl group (C=O).
09

Draw the product for example 3

The product formed in example 3 is Cyclohexanone, which has the formula C6H10O. Its structure is a six-membered ring with a carbonyl group (C=O) attached to one of the carbon atoms.

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Most popular questions from this chapter

When \((R)-2\) butanol is left standing in aqueous acid, it slowly loses its optical activity. Account for this observation.

Malve a new bond between a nucleophile and an electrophile and simultaneously break a bond to give stable molecules or ions. Nucleophilic displacement of MEO by Br gives the bromoalkane. ONCCCBr

Using your roadmap as a guide, show how to convert 2-methylpentane into 2-me- thylS-pentanote Show all reagents needed and all molecules synthesized along the way. CCC(C)C(O)CC 2-Methylpentane 2-Miethy13-pentanone Reactions in Context

Draw structural formulas for the alkenes formed on acid-catalyzed dehydration of each alcohol. Where isomeric alkenes are prossible, predict which alkene is the major product. (a) 3.Methyl-butanol (racemic) (b) 2 Methylcyclopentanol (racemic)

When isomeric alkenes are obtained in acid catalyzed dehydration of an alcohol, the alkene having the greater number of substituents on the double bond (the more stable alkene) generally predominates (Zaitsev's rule, Section 9.5).
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