1-bromopropane is a minor product of a reaction. Explain why 2-bromopropane is the major product of that reaction?

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1-bromopropane is a minor product of a reaction. Explain why 2-bromopropane is the major product of that reaction?

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Answer 1 · 2018-04-23T16:41:05

You have not specified the reaction but let us try:

$H_{2} C = C H - C H_{3} (g) + D B r (g) \to H_{2} D C - C H B r C H_{3}$ $H_2C=CH-CH_3(g) + DBr(g) rarr H_2DC-CHBrCH_3$

Explanation:

Now we perform hydrohalogenation with $D B r \equiv^{2} H B r$ $DBr-=""^(2)HBr$ so that we can follow the process. We start with propylene...the which reacts with the protium ion....

$H_2C=CH-CH_3 + DBr rarr underbrace(H_2DC-stackrel(+)CH-CH_3)_"stabilized intermediate"+Br^(-)$
$" "underbrace(H_2stackrel(+)C-CHD-CH_3)_"primary carbocation"$

From the unsymmetrical olefin, the protium ion of $""^2HBr$ can add to $"carbon 1"$ to give a $2^@$ $"carbocation"$ , or add to $"carbon 2"$ to give a $1^@$ $"carbocation"$ . We assume the $2^@$ $"carbocation"$ is stabilized with respect to the $1^@$ $"carbocation"$ ..and so the reaction should follow the lower energy route.

And so the end result should be the secondary alkyl halide as the major product....

$H_2C=CH-CH_3 + DBr rarr underbrace(H_2DC-CHBr-CH_3)_"major product"$
$" "underbrace(BrH_2C-CHD-CH_3)_"minor product"$

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1-bromopropane is a minor product of a reaction. Explain why 2-bromopropane is the major product of that reaction?

1 Answer

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