Suggest reasonable explanations for each of the following observations: The firs

Question

Suggest reasonable explanations for each of the following observations: The first-order rate constant for the solvolysis of (CH_3)_2C=CHCH_2Cl in ethanol is over 6000 times greater than that of allyl chloride (25 degree C). After a solution of 3-buten-2-ol in aqueous sulfuric acid had been allowed to stand for 1 week, it was found to contain both 3-buten-2-ol and 2-buten-l-ol. Treatment of CH3CH=CHCH_2OH with hydrogen bromide gave a mixture of 1-bromo-2-butene and 3-bromo-1-butene. Treatment of 3-buten-2-ol with hydrogen bromide gave the same mixture of bromides as in part (c). The major product in parts (c) and (d) was 1-bromo-2-butene.

Explanation / Answer

Q52

a)

the ethanol is very polar, therefore solvolysis is carreid out faster than in the linear alll chloride

b)

the reate of reaction for 2-buten-1-ol is slower, thereofre, after 1 day, expect reaction between the acid + 3-buten-2-ol

c)

The mixture is due to the stability of both carbocations, it will not follow Markonikov rules and will react with both, the alkene + alcohol OH group

d)

3-buten-2-ol has 2 gropus, "en" group which is alkene, and "ol" group which is OH, as stated before, the reaciton goes toward both groups reactions

e)

major group is 1-bromo-2-butene since the bromo group is much more likely to attack the OH gropu, then 2-butene is going to keep C=C most likely

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