(Solved): 7 Halogens and their compounds are commonly used in organic reactions to symesise new compounds. 6 ...

7 Halogens and their compounds are commonly used in organic reactions to symesise new compounds. 6.7 of compound

, reacts with

of chlorine gas (at r.t.p.) to give compound B. On addition of

, A gives white fumes. Treatment of

with HBr heated under reflux gives compounds C and D. Both C and D have the same molecular formula

and each contains only one chiral centre. (a) Use the information to deduce the structural formulae of

. Explain the reactions that occur. In particular, state clearly the type of reaction(s) undergone by A with NaBr and concentrated

described above. (b) State and explain which compound,

or

, is produced in greater quantity. (c) Describe the mechanism of the reaction between A and

, including curly arrows showing the movement of electrons, and all charges. [10] RJC 2011 H2 Prelim P3 Q11