Question

1. Propyne is first treated with sodium amide to generate a reactive intermediate, A. This first reaction is a Br nsted acid-Br nsted base reaction. A is combined with benzyl bromide, giving product B, having molecular formula C10H10. Some pKa’s are provided to help you guess the structure of A. H3C — C ? C — H pKa > 40 pKa = 25 Na+ NH2- the conjugate acid of NH2- is NH3 which has pKa = 36 A Br B C10H10

          1. Propyne is first treated with sodium amide to generate a reactive intermediate, A. This first reaction is a Br    nsted acid-Br    nsted base reaction. A is combined with benzyl bromide, giving product B, having molecular formula C10H10. Some pKa’s are provided to help you guess the structure of A.

H3C — C ? C — H
pKa > 40
pKa = 25

Na+ NH2-
the conjugate acid of NH2- is NH3 which has pKa = 36

A
Br
B C10H10

1. Propyne is first treated with sodium amide to generate a reactive intermediate, A. This first reaction is a Br nsted acid-Br nsted base reaction. A is combined with benzyl bromide, giving product B, having molecular formula C10H10. Some pKa’s are provided to help you guess the structure of A.

H3C — C ? C — H
pKa > 40
pKa = 25

Na+ NH2-
the conjugate acid of NH2- is NH3 which has pKa = 36

A
Br
B C10H10

Added by Jennifer A.

Chemistry: Structure and Properties

Nivaldo Tro 2nd Edition

Instant Answer

Solved by Expert Madhur L

12/12/2022

Step 1

The acidic hydrogen atom with a pKa of 25 is abstracted by the strong base NH2-, resulting in the formation of the reactive intermediate A. ** Show more…

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Propyne is first treated with sodium amide to generate a reactive intermediate A. This first reaction is a Brønsted acid-Brønsted base reaction. A is combined with benzyl bromide, giving product B, having molecular formula C10H10. Some pKa’s are provided to help you guess the structure of A. H3C—C≡C—H pKa > 40 pKa = 25 Na+ NH2- the conjugate acid of NH2- is NH3 which has pKa = 36 A Br B C10H10