Chem

Organic Chemistry I Spring 2013 Practice test 1. Name the following compounds: a. 5-tert-butyl-7-isopropyl-6-sec-butyl-undecane b. cis-2-(5,6-dimethylheptyl)-6-(3-methylpentyl)piperidine c. trans -2-nonyl-3-octyl-tetrahydrofuran d. trans-1,6-dimethylbicyclo[4. 3. 0]nonane e. cis-6,8-ditert-butylspiro[3. 5]nonane f. 1,6-dimethylcyclohexene g. (Z)-3-bromo-4-fluoro-5-methyl-oct-4-ene h. (E)-8-(1-chloroethyl)nonadec-8-ene 2. Draw the structures of the following compounds: a b e c f d g h 3.Draw the structure of the following compounds in Newman projections and in chair conformations: a b c d e 4. Draw the most stable isomer of 1-tert-butyl-3-methylcyclohexane. a. Which atoms/groups are i. gauche to axial hydrogen on C2 A: t-butyl, C6, methyl, C4 ii. anti to equatorial substituent on C3 A: C5, C1 b. What is the relationship between: i. tert-butyl group and equatorial hydrogen on C2 A: gauche ii. equatorial hydrogen on C4 and C6 A: anti 5. Draw all isomers of 4-tert-butyl-2-ethyl-1-methylc yclohexane (ignore mirror images) in their most stable conformations.Arrange the structures from the least stable to the most stable. 6. Cyclohexylmethanol and 1-methylcyclohexanol are converted to their corresponding bromides. Write a suitable mechanism for each reaction, and assign each the appropriate symbol (SN1 or SN2). OH O H H Br H + :Br : SN2 :Br : O H H Br + H2O OH O H Br O + H2O + :Br : SN1 :Br : Br 7. Give the structure of the principal organic product formed by photochemical bromination of methylcyclopropane, draw the mechanism of the reaction. Br2, h? h? Br Br H . .Br Br Br Br 2Br . . + HBr Br + . Br