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18-06-2022
Chemistry

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DH
QUESTION 1
[11]
Give reasons that might help to explain the following observations:
a)
A student was unsuccessful to prepare a Grignard reagent from 4-bromocyclohexanol.
b)
Benzenesulfonic acid does not undergo Friedel-Crafts alkylation.
c)
(2S, 3R)-2,3-Dibromobutane has a specific rotation, [a]o, of 0°.
d)
A student tries to prepare an ether via the Williamson ether synthesis from ethanol and
t-butyl bromide, but obtains an alkene instead.
e)
Doubling the concentration of a nucleophile has no effect on the rate of a substitution
reaction.

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20-06-2022

a. 4- bromocyclohexanol is an acidic proton

b. Benzenesulfonic acid deactivates the entire process

c. (2S, 3R)-2,3-Dibromobutane are racemic mixtures

d. Williamson synthesis cannot be used with tertiary alkyl halides

e. Nucleophiles are not involved in the rate determining step

The reasons that might help to explain the following observations are:

a. Grignard reagents cannot be made if acidic functional groups are also present in the halogen compound and it is also destroyed by reaction with acidic hydrogen atoms of water, alcohols, phenols, or carboxylic acid groups.

4-bromocyclohexanol is an acidic proton compound

b. Benzenesulfonic acid does not undergo Friedel-Crafts alkylation because the carboxylic group causes deactivation, carboxylic group and the Lewis acid catalyst are also bonded in the process.

c. (2S, 3R)-2,3-Dibromobutane has a specific rotation, [a]o, of 0° are racemic mixtures having equal and opposite specific rotations and a racemic mixture has a specific rotation of zero (0°)

d. This is because the Williamson synthesis cannot be used with tertiary alkyl halides which in this case is t-butyl bromide because they undergo elimination reactions instead of participating in SN2 reactions and form alkenes instead of ethers.

e. Doubling the concentration of a nucleophile has no effect on the rate of a substitution reaction because the nucleophile is not involved in the rate-determining step of the SN-1 reaction.

Learn more about organic reactions here:

https://brainly.com/question/3529377

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