How to convert CH3-CHBr-CH3 into CH3-CHOH-CH2Br ?

i would prefer if anyone could give me the answer in minimum number of steps =)

Answer 1

Huh, I can't think of more than one good path. There are others, but they won't give as good of a yield because the alkyl halide is a secondary alkyl halide, which is not great for #"S"_N2#, ruling that out in the first step for the best possible synthesis.

Here's what I came up with:

The first step is a second order elimination (#E2#) via a strong bulky base like tert-butoxide in tert-butanol. (Tert-butoxide is also known as 2-methyl-propan-2-ol.) Bromine is the leaving group here, and tert-butoxide steals a proton off of carbon-1.

The second step is not one you would normally think you need to use (it might have been introduced as a reaction you want to try to avoid happening when brominating), but it works here.

Bromine adds across the double bond first as a cyclopropane analog, and then water, as a stronger nucleophile, intercepts before the other bromine attacks.

Water targets the carbon where the resultant carbocation is more stable, so it targets carbon-2. The result is a product of Markovnikov anti addition (as opposed to syn addition).

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Answer 2

To convert CH3-CHBr-CH3 into CH3-CHOH-CH2Br, you can perform a nucleophilic substitution reaction using a strong base such as hydroxide ion (OH^-). This reaction, known as an elimination-addition reaction, replaces the bromine atom with a hydroxyl group. The steps involve deprotonation of one of the methyl groups by the strong base followed by attack of the nucleophile (OH^-) on the electrophilic carbon. This results in the formation of the desired product CH3-CHOH-CH2Br.

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Answer from HIX Tutor

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

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