Nucleophilic substitution questions

Assignment: Questions on Topic 20.1: Nucleophilic substitution

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1

Explain the following statements:

i.  hydroxide ions are better nucleophiles than water molecules.

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ii. the hydrolysis of iodoethane is faster than the hydrolysis of bromoethane.

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iii.  the hydrolysis of 2-bromo-2-methylpropane is faster than the hydrolysis of 1-bromobutane.

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iv.  fluoroethane does not react with dilute sodium hydroxide solution to form ethanol.

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2

Explain the mechanism for the reaction of ammonia with bromoethane. (Use curly arrows to show the movement of pairs of electrons and upload your answer as an image or a pdf file.)

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3

i. Explain why the substitution of primary halogenoalkanes by hydroxide ions could also be classed as a Lewis acid-base reaction.

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ii. Explain whether the reaction of tertiary halogenoalkanes with hydroxide ions could also be classed as a Lewis acid-base reaction.

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4

Suggest how tetramethylammonium bromide, (CH3)4N+Br–, could be made from bromomethane.

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