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Chapter 11: 7P (page 426)

Draw the organic products formed when each alkyne is treated with two equivalents of HBr.

a.

b.

c.

Short Answer

Expert verified

a.

b.

c.

Step by step solution

01

Addition of hydrogen bromide to an alkyne

Alkynes can undergo the addition of hydrogen bromide, and this is an electrophilic addition.Two moles of HBr are used. The first mole will react with alkyne to form vinyl halide, which will then react with another mole of HBr and form a geminal halide.

02

Mechanism

The mechanism of the reaction taking place is shown using an example below:

Mechanism of the addition of HBr to but-1-yne

03

Formation of the final product

a. The reaction taking place between hex-1-yne and HBr is shown below:

Addition of HBr to hex-1-yne

b. The reaction taking place between ethynylcyclohexane and HBr is shown below:

Addition of HBr to ethynylcyclohexane

c. The reaction taking place between 3-ethynyl-1,1-dimethylcyclopentane and HBr is shown below:

Addition of HBr to 3-ethynyl-1,1-dimethylcyclopentane

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Most popular questions from this chapter

Question: When alkyne a is treated with NH2 followed by CH3 , a product having the molecular formula C6H10O is formed, but it is not compound B. What is the structure of the product and why is it formed?

Question: Explain the apparent paradox. Although the addition of one equivalent of HX to an alkyne is more exothermic than the addition of HX to an alkene, an alkene reacts faster with HX.

Question: Devise a synthesis of CH3CH2C≡CCH2CH2OHfromCH3CH2OHas the only organic starting material. You may use any other needed reagents.

Question: Draw the organic products formed in each reaction.

a.

b.

c.

d.

e.

f.

g.

h.

i.

j.

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See all solutions

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