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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 鈫� 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鈥檚 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: Prepare each compound from cyclopentanol. More than one step may be needed.

a.

b.

c.

d.

Question: Explain the following observation. When 3-methylbutan-2-ol is treated with HBr, a single alkylbromide is isolated, resulting from a 1,2-shift. When 2-methylpropan-1-ol is treated with HBr, no rearrangement occurs to form an alkyl bromide.

Question: Answer each question using the ball-and-stick model of compound A.

a. Give the IUPAC name for A, including R,Sdesignations for stereogenic centers.

b. Classify A as a 1掳,2掳,3掳alcohol.

c. Draw a stereoisomer for A and give its IUPAC name.

d. Draw a constitutional isomer that contains an OH group and give its IUPAC name.

e. Draw a constitutional isomer that contains an ether and give its IUPAC name.

f. Draw the products formed (including stereochemistry) when A is

treated with each reagent: [1] NaH; [2] ; [3] , pyridine;

[4] HCl; [5] ,pyridine; [6] TsCl, pyridine.

Question: Show how a 1,2-shift forms a more stable carbocation from each intermediate.

a.

b.

c.

Question: Draw the products of each reaction, indicating the stereochemistry around any stereogenic centers.

a.

b.

c.
See all solutions

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