If you were to monitor your reaction progress using silica TLC, would you expect the tert- butyl bromide or the tert-butanol to move higher up the TLC plate? Justify vour answer by describing the interactions with silica (5 pts): Would you expect the tert-butyl bromide or the tert-butanol to have a higher boiling point? Describe the intermolecular forces present in each to justify your answer (4 pts). Student A is going to perform the following Swl reaction: Ph HzO Draw the product(s): Include stereochemistry for full credit (5 pts): Student B wants to obtain only one stereoisomer. Will this reaction give one stereoisomer? Explain why or why not: (5 pts) The student wants the reaction to go faster, so the student doubles the amount of nucleophile (water) in the reaction. Will this work? Explain: (5 pts)

a) If you were to monitor your reaction progress using silica TLC, would you expect the tert- butyl bromide or the tert-butanol to move higher up the TLC plate? Justify your answer by describing the interactions with silica.

The tert Butanol will move to the top along with the solvent on the TLC plate.
As the silica gel is the polar in nature tert- butyl bromide being more polar than tert- Butanol it will interact with the silica of the TLC to the more extent.
Due to this interaction between tert-butyl bromide and silica the sample the tert-butyl tert butyl bromide will stay below the tert Butanol.
Due to electronegativity of bromide ion tert Butanol become more polar.
And as per polar-polar interaction the tert butyl bromide.

b) Would you expect the tert-butyl bromide or the tert-butanol to have a higher boiling point? Describe the intermolecular forces present in each to justify your answer.

Out of tertiary bromide or tertiary alcohol, the tertiary alcohol has more boiling point than tertiary alkyl halide.
This is because alcohol has hydrogen bonding with water or itself but tertiary bromide do not show hydrogen bonding.
Tertiary hydrogen bonding is strong forces than the vander waal or london forces .
Hence due to Hydrogen bonding tertiary alcohol has higher boiling point.

c) The student wants the reaction to go faster, so the student doubles the amount of nucleophile (water) in the reaction. Will this work?

Nucleophile won't have much effect on speed because it isn't part of rate determining step.

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