Question

A compound of molecular formula C7H13Br is a tertiary bromide, is optically inactive, and has one primary carbon atom. C7H13Br is inert to catalytic hydrogenation. C7H13Br is reacted with another unknown compound. Thin-layer chromatography of the product mixture shows that two products are formed. GC analysis shows that the two products are formed in unequal amounts. Upon isolation from each other via distillation, both isolated products are optically inactive. Both products de-colorize molecular bromine.

Answer questions a-c below.

a. Based on the information provided, is the reaction between the tertiary bromide and the unknown compound a: 1. substitution, or 2. elimination reaction? ________

b. Will the organic starting material give a positive (P) or negative (N) result for the silver nitrate in alcohol test? ________

c. Propose a structure for C7H13Br. Name the structure.

Answer 1

The compound in question must be

This has one primary carbon, it is optically inactive, it cannot be catalytically hydrogenated.

Upon reaction with a base it will produce a 2 isomers of methyl cyclohexene and they will be in inequal quantities due to the presence of the CH₃ unit.

Both these products will decolorize molecular bromine

Answer questions a-c below.

a. Based on the information provided, is the reaction between the tertiary bromide and the unknown compound a: 1. substitution, or 2. elimination reaction?

The answer will be it is an elimination reaction

b. Will the organic starting material give a positive (P) or negative (N) result for the silver nitrate in alcohol test?

The silver nitrate in alcohol test will give a positive result with this compound

c. Propose a structure for C7H13Br. The structure has been put in the beginning

The name of the compound is 1-bromo-3-methylcyclohexane