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Chapter 10: PROBLEM 10.58 (page 423)

Question: Draw a stepwise mechanism for the conversion of hex-5-en-1-ol to the cyclic ether A.

Short Answer

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Answer

Step by step solution

01

Intramolecular reaction  

Intramolecular cyclization occurs due to the presence of one Lewis donor group and one pi acceptor group. The reactivity of intramolecular cyclization is enhanced by the presence of acids

02

Formation of cyclic ethers

The intramolecular reaction of oxygen with alkene (donation of non-bonding electrons of oxygen to the vacant pi orbital of alkene) leads to cylic ether.

03

Explanation

The alkene first reacts with sulfuric acid to generate the carbocation. Next, the OH group attacks the positive charge on carbon and cyclizes.

The mechanism is shown below:

Reaction mechanism

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Most popular questions from this chapter

Question: Devise a synthesis of each compound from cyclohexene as the starting material. More than one step is needed.

a.

b.

c.

d.

Question: What alkylborane is formed from hydroboration of each alkene?

Question: What alkene can be used to prepare each alcohol as the exclusive product of a two-step hydroboration鈥搊xidation sequence?

Question: Which alkene reacts faster with HBr? Explain your choice

Question: Draw the constitutional isomer formed when the following alkenes are treated with each set of reagents: [1] H2O,H2SO4; or [2] BH3followed by H2O2,HO-.
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