Sergey Bylikin, Gary Horner and, Brian Murphy Solutions for Chapter: Organic Chemistry [AHL], Exercise 5: Questions

${\mathrm{C}}_5{\mathrm{H}}_{11}\mathrm{Br}+\mathrm{NaOH}\to {\mathrm{C}}_5{\mathrm{H}}_{11}\mathrm{OH}+\mathrm{NaBr}$

The reaction with 1-bromopentane proceeds by an ${\mathrm{S}}_{\mathrm{N}}2$ mechanism. Describe this mechanism using structural formulas and curly arrows to represent the movement of electron pairs.

${\mathrm{C}}_5{\mathrm{H}}_{11}\mathrm{Br}+\mathrm{NaOH}\to {\mathrm{C}}_5{\mathrm{H}}_{11}\mathrm{OH}+\mathrm{NaBr}$

The reaction with 2-bromo-2-methylbutane proceeds by an ${\mathrm{S}}_{\mathrm{N}}1$ mechanism. Describe this mechanism using structural formulas and curly arrows to represent the movement of electron pairs.

Explain why 1-bromopentane reacts by an ${\mathrm{S}}_{\mathrm{N}}2$ mechanism whereas 2-bromo-2-methylbutane reacts by an ${\mathrm{S}}_{\mathrm{N}}1$ mechanism.

Explain whether the boiling point of 1-bromopentane will be higher, lower, or the same as that of 2-bromo-2- methylbutane.

${\mathrm{C}}_5{\mathrm{H}}_{11}\mathrm{Br}+\mathrm{NaOH}\to {\mathrm{C}}_5{\mathrm{H}}_{11}\mathrm{OH}+\mathrm{NaBr}$

The product ${\mathrm{C}}_5{\mathrm{H}}_{11}\mathrm{OH}$ formed from the reaction with 1-bromopentane is warmed with ethanoic acid in the presence of a few drops of concentrated sulphuric acid. State the name of the type of reaction taking place and the structural formula of the organic product.

Deduce a multi-step synthesis for each of the following conversion. For each step state the structural formulae of the reactants and products and the conditions used for the reactions.

2-chlorobutane to butan-2-one (2 steps)

Deduce a multi-step synthesis for each of the following conversion. For each step state the structural formulae of the reactants and products and the conditions used for the reactions.

Propene to propyl ethanoate (2 steps)

Deduce a multi-step synthesis for each of the following conversions. For each step state the structural formulae of the reactants and products and the conditions used for the reactions.

benzene to aniline (phenylamine) (3 steps)