Answer $2-$Yes$6$

In the distillate, which layer $($organic or aqueous$)$ is on top? Why? If you were not sure, how could you confirm this?

The organic layer is treated with concentrated sulfuric acid $($density $=1\mathrm{.}84\frac{g}{m}L)$ and the mixture is then poured into the separatory funnel. Which layer in the funnel contains the alkyl bromide? Explain.

Pre$-$lab questions

Draw the structures of the three alcohol starting materials: $1-$butanol, $1-$pentanol, and $3-$methyl$-1-$butanol. Classify each alcohol as primary, secondary or tertiary.

In this experiment, the alcohols listed in question $1$ are reacted with NaBr and $H_{2}S{O}_4$ to produce the corresponding alkyl bromide. By what reaction mechanism do you expect these alcohols to react to produce the alkyl bromides? Draw a mechanism, using curved arrows.

How could you distinguish between an alcohol and an alkyl bromide based on their IR spectra?

Draw the structures of the three possible alkyl bromide products: $1-$bromobutane, $1$bromopentane, and $1-$bromo$-3-$methylbutane.

For each alkyl bromide, indicate the number of distinct NMR proton environments. $($This number is the same as the number of signals you would expect to see in the spectrum, assuming no overlap.$)$ Draw each of the three molecules to explicitly show all hydrogens, then clearly label each proton environment using a letter.

For each alkyl bromide indicate the approximate chemical shift, multiplicity and number of protons for the signals corresponding to the environments identified in question $5.$

What intermolecular forces exist between alkyl bromide molecules? What intermolecular forces exist between alcohol molecules? How does this difference affect the boiling points of the two types of compounds?

The following questions should be answered by referring to the experimental procedure. Alkyl bromide densities are $1\mathrm{.}2-1\mathrm{.}3\frac{g}{m}L.$

Mechanistically speaking, why is concentrated sulfuric acid added to the reaction mixture?

During the distillation the product distills with water at a temperature below the boiling point of water. What is the name for this type of distillation?