Draw the three-dimensional representations of the two stereoisomers of $\text{CH}_3(\text{CH}_2)_5\text{CHBrCH}_3$. $R$ may be used for $\text{CH}_3(\text{CH}_2)_5$.
A sample of $\text{CH}_3(\text{CH}_2)_5\text{CHBrCH}_3$ reacts with NaOH to produce $\text{CH}_3(\text{CH}_2)_5\text{CH(OH)CH}_3$ by an $\mathrm{S_N1}$ mechanism. Complete Fig. 4.1 to show the mechanism for the reaction of $\text{CH}_3(\text{CH}_2)_5\text{CHBrCH}_3$ with NaOH. Add charges, dipoles, lone pairs of electrons and curly arrows where appropriate.
Separate portions of $\text{CH}_3(\text{CH}_2)_5\text{CHBrCH}_3$, $\text{CH}_3(\text{CH}_2)_5\text{CH(OH)CH}_3$ and $\text{CH}_3(\text{CH}_2)_5\text{CHCH}_2$ are each tested with different reagents. Complete Table 4.1. If there is no reaction, enter $\times$ in the appropriate box.
Name the type of reaction involved.
Identify D and state the conditions used.
A molecule of E contains both $\sigma$ and $\pi$ bonds because the carbon atoms have different hybridisations. Complete Table 4.2 to show the number of carbon atoms with each hybridisation type in a molecule of E.
Describe the essential feature of an unbranched hydrocarbon that makes its molecules capable of stereoisomerism. Explain how this feature leads to stereoisomerism.