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Chapter 11: Q27P (page 570)

When the following substituted cycloheptanol undergoes dehydration, one of the minor products has undergone a ring contraction. Propose a mechanism to show how this ring contraction occurs.

Short Answer

Expert verified

Dehydration reactions are the opposite of hydration reactions. They involve the deprival of water molecule from the reacting species. Fischer esterification is an example of dehydration reaction.

Step by step solution

01

Dehydration

Dehydration reactions are the opposite of hydration reactions. They involve the deprival of water molecule from the reacting species. Fischer esterification is an example of dehydration reaction.

02

Ring contraction

Ring contractions constitute a part of organic reactions like the cyclization reaction. Smaller and strained rings are transformed into larger rings in the ring contraction.

03

Mechanism showing the ring contraction when cycloheptanol undergoes dehydration

The dehydration of the given alcohols happens via the protonation of OH followed by the carbocation formation and stabilization. The carbocation stabilization happens via the 1, 2-methyl shift, which causes ring contraction. The mechanism can be given as:

Mechanism of ring contraction

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Most popular questions from this chapter

Show how you would synthesize the following compounds. As starting materials, you may use any alcohols containing four or fewer carbon atoms, cyclohexanol, and any necessary solvents and inorganic reagents.
Propose a mechanism for each reaction.

(a)

(b)

(c)

(d)

Neopentyl alcohol, (CH3)3CCH2OH, reacts with concentrated HBr to give 2-bromo-2-methylbutane, a rearranged product. Propose a mechanism for the formation of this product.

Predict the products of the sulfuric acid-catalyzed dehydration of the following alcohols. When more than one product is expected, label the major and minor products.

(a) 2-methylbutan-2-ol (b) pentan-1-ol (c) pentan-2-ol

(d) 1-isopropylcyclohexanol (e) 2-methylcyclohexanol

To practice working through the early parts of a multistep synthesis, devise syntheses of

(a) pentan-3-one from alcohols containing no more than three carbon atoms.

(b) 3-ethylpentan-2-one from compounds containing no more than three carbon atoms.
See all solutions

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