a)
Interpretation:
Assuming that halogens add to
Concept introduction:
Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the halogens to yield a tetrahaloalkane derivative. In the first step of the addition reaction the nucleophilic attack of the π electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.
To propose:
A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Br2 adds to 2-butyne assuming that bromine adds to alkynes in the same manner as they add to alkenes.
b)
Interpretation:
Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Cl2 adds to 1-phenylpropyne is/are to be predicted.
Concept introduction:
Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the reagents to yield a tetrahaloalkane as the product. In the first step of the addition reaction, the nucleophilic attack of the π electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.
To propose:
A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Cl2 adds to 1-phenylpropyne assuming that chlorine adds to alkynes in the same manner as they add to alkenes.
c)
Interpretation:
Assuming that halogens add to alkynes in the same manner as they add to alkenes, a mechanism is to be proposed and the product(s) expected for the reaction in which two equivalents of Br2 adds to 1-pentyne is/are to be predicted.
Concept introduction:
Alkynes when treated with one equivalent of a halogen yield a dihaloalkene as the product. They react with two equivalents of the reagents to yield a tetrahaloalkane as the product. In the first step of the addition reaction the nucleophilic attack of the π electrons of the double/triple bond in alkene/alkyne on a halogen results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. In the second step the halide ion attacks the cyclic halonium ion to yield the product.
To propose:
A mechanism and to predict the product(s) expected for the reaction in which two equivalents of Br2 adds to 1-pentyne assuming that bromine adds to alkynes in the same manner as they add to alkenes.
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Chapter 9 Solutions
Bundle: Organic Chemistry, Loose-leaf Version, 9th + LMS Integrated for OWLv2, 4 terms (24 months) Printed Access Card
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