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Chapter 12: Q19E (page 354)


Assuming that strong acids add to alkynes in the same manner as they add to alkenes, propose a mechanism for each of the following reactions:

Short Answer

Expert verified

The mechanisms of the reactions are given below.

a).

b).

c).

Step by step solution

01

Addition of   to alkyne

The mechanism of addition of halogen acids to alkynes is similar to addition to alkenes. Alkynes contain two pi bonds and hence two equivalents of acid can be added to one molecule of an alkyne. The general mechanism for addition to alkynes is given below. In the first step of the reaction a stable carbocation is generated. The nucleophile attacks the carbocation. The product formed after addition of one molecule of HX gives an alkene. Further addition takes place following the same mechanism to give germinal dihalide as the product.

X = Cl, Br

02

Addition   to Pentyne

Addition of hydrochloric acid takes place with carbocation formation. The mechanism for the reaction is given below

03

Addition HBr to But-2-yne

The addition of HBracid takes place with carbocation formation. The mechanism of the reaction is given below.

04

Addition HBr to phenylacetylene

Addition of hydrochloric acid takes place with an intermediate of carbocation.

Then lead to the formation of required product.

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Most popular questions from this chapter

Ketones undergo a reduction when treated with sodium borohydride, NaBH4

. What is the structure of the compound produced by reaction

of 2-butanone with NaBH4 if it has an IR absorption at 3400 cm-1 and M+ = 74in the mass spectrum?

At what approximate positions might the following compounds showIR absorptions?

(d)

Most stable organic species have tetravalent carbon atoms, but species with trivalent carbon atoms also exist. Carbocations are one such class of compounds.

(a) How many valence electrons does the positively charged carbon atom have?

(b) What hybridization do you expect this carbon atom to have?

(c) What geometry is the carbocation likely to have?

Predict the product(s) and provide the mechanism for each reaction below. What does each mechanism have in common?

b.

c.

d.

Question: Where might the following compound have IR absorptions?
See all solutions

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