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Chapter 9: Q12. (page 346)

Question: Rank the alcohols in order of increasing reactivity when dehydrated with H2So4

Short Answer

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Answer

The alcohols in order of increasing reactivity, when dehydrated with H2So4are mentioned below.

Step by step solution

01

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

The elimination of water molecules from alcohol in the presence of acid is termed the dehydration of alcohol.

02

Order of ease of dehydration of alcohol and stability of carbocation

The decreasing order of the ease of the dehydration of alcohol in the presence of acid is given as follows.

3°alcohol>2°alcohol>1°alcohol

The above order is dependent on the stability of the carbocation. The order is given as follows.

3°alcohol>2°alcohol>1°alcohol

03

Order of increasing reactivity

The formation of a carbocation in the given compounds is as follows.

Order of carbocation

Thus, the increasing order of dehydration is shown below.

Order of dehydration

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Most popular questions from this chapter

Question: Draw a stepwise mechanism for the following reaction.

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: What alkyl halides are formed when each ether is treated with HBr?

a.

b.

c.

Question: Epoxides are converted to allylic alcohols with non-nucleophilic bases such as lithiumdiethylamide [LiNCH2CH32] . Draw a stepwise mechanism for the conversion of1,2-epoxycyclohexane to cyclohex-2-en-1-ol with this base. Explain why a strong bulky basemust be used in this reaction.

Question: Draw the products formed when (S)-butan-2-ol is treated with TsCl and pyridine, followed by NaOH. Label the stereogenic center in each compound as R or S. What is the stereochemical relationship between the starting alcohol and the final product?
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