(Solved): Question 3 [30 marks] a) Give the molecular formula and draw the skeletal structure for 3-bromo-3- ...

Question 3 [30 marks] a) Give the molecular formula and draw the skeletal structure for 3-bromo-3- methylhexane. [2 marks] b) Name (including E/Z stereochemistry) the FIVE alkenes that can produce 3-bromo-3- methylhexane on reaction with HBr. Draw the skeletal structure of each molecule. [10 marks] c) Define the type of stereoisomerism present in 3-bromo-3-methylhexane. Name and draw the tetrahedral representation of the two stereoisomers. [5 marks] d) For the base-catalysed hydrolysis of 3-bromo-3-methylhexane (i.e. reaction with the nucleophile OH"): i) State whether the reaction is likely to proceed by an SN1 or SN2 mechanism, and explain your choice. [3 marks] Give the likely rate law for the reaction. Explain your choice. [2 marks] For the reaction intermediate, draw its structure and give the VSEPR description of the geometry at the reaction centre. [3 marks] Give the names and draw the structures of the two reaction products. Explain your conclusions. [5 marks] iii) iv)