Please answer all questions. Be sure to show clear working.

Q1. Consider the molecule 3-chloro-2,2,4,5-tetramethylhexane and answer the following questions. i. Draw the full Kekule representation for this molecule clearly identifying the C3-C4 bond in the box below. [2 marks] ii. Draw the Newman projection diagram for the most stable conformation of this molecule looking down the C3-C4 bond. [4 marks] Q3. Name each of the following compounds using IUPAC nomenclature. ii. ii. [22 marks] Q5. Bromination of 3-methylpentane gives a mixture of four monobrominated products. i. Draw and name (using the IUPAC system) the products. ii. Identify the major product and outline a probable mechanism for its formation