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Chapter 9: Q13. (page 347)

Question: Draw the structure of each transition state in the two-step mechanism for the reaction.

CH3CH2OH + H2So4 → CH3CH=CH2+ H2O

Short Answer

Expert verified

Answer

The mechanism is shown below.

Step by step solution

01

Step-by-Step Solution Step 1: Dehydration of an alcohol

The reactivity of the dehydration of alcohol depends upon the carbocation’s stability. The first step of the dehydration of alcohol is the formation of a carbocation.

02

Formation of carbocation

In the first step, the oxygen abstracts a proton from an acid (followed by the removal of water) to form carbocation, as shown below.

Formation of carbocation

03

1,2 hydride shift and product formation

In the second step, the 1,2-hydride shift takes place. The product is formed by the deprotonation, as shown below.

Formation of the product

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Most popular questions from this chapter

Question: Treatment of cis-4-bromocyclohexanol with HO– affords compound A and cyclohex-3-en-1-ol. Treatment of trans-4-bromocyclohexanol under the same conditions forms compound B and cyclohex-3-en-1-ol. A and B contain different functional groups and are not isomers of each other. Propose structures for A and B and offer an explanation for their formation

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