An unknown compound is treated with bromine, cold, uv light (reaction 1). The predominant product of this reaction is treated with sodium ethoxide (reaction 2). The product of reaction 2 is reacted with HBr and peroxide (reaction 3). The product of reaction 3 is reacted with lithium acetylenide (reaction 4). This product is treated with lithium then bromoethane (reaction 5). In reacțion 6, the product of reaction 5 is reduced with hydrogen, using Lindlar's catalyst. This fina product is determined to be 6-methyl-cis- 3-heptene (below). Name the original compound and list the names of the major product of each reaction. Y

Mechanism of azide synthesis: Step 1: Nucleophilic substitution of alkyl halide with sodium azide to form an alkyl azide. Step 2: Reduction of alkyl azide with a reducing agent such as sodium borohydride or lithium aluminum hydride to form an alkylamine. Mechanism of alkylation of ammonia: Step 1: The alkyl halide undergoes a nucleophilic substitution reaction with ammonia gas to form an intermediate alkylamine. Step 2: The intermediate alkylamine is deprotonated by the catalyst to form the final alkylamine.

Which of the following statements is false with respect to the two reactions shown below? HBr, ether **. Br2, THF The mechanism of the bottom reaction involves a three-membered ring intermediate. The mechanism of the top reaction involves a tertiary carbocation. O Both reactions result in a set of enantiomers. O The mechanism of the top reaction involves a three-membered ring intermediate. O The top reaction follows Markovnikov's rule.

Draw the major product of this reaction. Ignore inorganic byproducts.