Chapter 7 Alkenes and Alkynes 1 Properties and Synthesis.

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Presentation transcript:

Chapter 7 Alkenes and Alkynes 1 Properties and Synthesis. Elimination Reactions of Alkyl Halides

Carbocation Stability and Transition State

Carbocation Stability and the Transition State The transition state that leads to the tertiary carbocation is lowest in free energy because it resembles the most stable product Secondary is not easily dehydrated and so as primary alcohol

Carbocation Stability and The Transition State

A Mechanism for Dehydration of Primary Alcohols: An E2 Reaction

A Mechanism for Dehydration of Primary Alcohols: An E2 Reaction

Rearrangements during Dehydration of Secondary Alcohols

Mechanism

The rearrangement of Carbocation Methyl group migrates with its pair of electrons (-:CH3 ion) 1,2 shift

The arrangement of Carbocation

The arrangement of Carbocation

Example Acid-catalyze dehydration of neopentyl, (CH3)3CCH2OH, yields 2-methyl-2-butene as the major product. Outline a mechanism showing all steps in its formation

Rearrangement after Dehydration of a Primary Alcohol

Rearrangement after Dehydration of a Primary Alcohol

Rearrangement after Dehydration of a Primary Alcohol

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