C1B Singly bonded functional groups.

Tutorial Questions

Spring 2014

1. Suggest synthetic routes to the following compounds using benzyl bromide (PhCH2Br) and any other necessary reagent as the starting materials. (a) PhCH2I (c) PhCH2NH2 (2 steps) (e) PhCH2CH2NH2 (2 steps) (g) PhCH2CCH (b) PhCH2CN (d) PhCH2SH (f) PhCH2OCH3 (h) CH3CO2CH2Ph

2.

Give the products of the following SN2 reactions, and indicate which will be optically active. Label the products R or S where appropriate.

3.

Complete the following SN1 reactions showing the intermediate carbocation in each case.

4.

For each of the following alkyl halides complete the equation showing the possible nucleophilic substitution and elimination products.

5.

How is epoxycyclohexane (A) prepared from cyclohexene?

Show, with mechanisms, the outcome of the reaction of A with: (a) (d) H3O+ NaCH / H2O (b) (e) MeOH / H+ MeONa / MeOH (c) NH3