Question
Download Solution PDFThe relative rate of dehydration of alcohols is given by:
Answer (Detailed Solution Below)
Detailed Solution
Download Solution PDFCONCEPT:
Dehydration of Alcohols
- Dehydration of alcohols refers to the elimination of a water molecule (H2O) from an alcohol to form an alkene.
- This reaction typically occurs in the presence of a strong acid catalyst such as concentrated sulfuric acid (H2SO4) or phosphoric acid (H3PO4).
- The rate of dehydration of alcohols depends on the stability of the carbocation intermediate formed during the reaction.
- Carbocation stability increases in the order:
3° (tertiary) > 2° (secondary) > 1° (primary)
EXPLANATION:
- During the dehydration process:
- The alcohol first undergoes protonation by the acid to form an oxonium ion (R-OH2+).
- This is followed by the loss of water (H2O), forming a carbocation intermediate.
- The stability of the carbocation intermediate is a key factor determining the rate of the dehydration reaction.
- The order of carbocation stability is:
3° (tertiary carbocation) > 2° (secondary carbocation) > 1° (primary carbocation)
- As tertiary alcohols form the most stable carbocations, they dehydrate the fastest. Secondary alcohols are next, followed by primary alcohols, which form the least stable carbocations.
Therefore, the relative rate of dehydration of alcohols is: 3° > 2° > 1°.
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