12. Which of the following alcohols will react most rapidly with the Lucas reagent (HCl, ZnCl₂)? 

8. SN1 reaction usually proceed with . (A) slightly more inversion than retention at the center undergoing substitution (B) slightly more retention then inversion at the center undergoing substitution (C) equal amounts of inversion and retention at the center undergoing substitution (D) complete inversion at the center undergoing substitution (E) complete retention at the center undergoing substitution

9. Peptide bonds are . (A) ester linkages (B) imido linkages (C) amide linkages (D) ether linkages (E) disulfide linkages

10. What is the major product of the following reaction?

11. What compound is produced when (CH3)2CHCH2Br is subjected to the following sequence of steps: 1. Mg, Et2O, 2. CO2, 3. H3O+ ? (A) 2-methylpropanoic acid (B) 3-methylpropanoic acid (C) 2-methylbutanoic acid (D) 3-methylbutanoic acid (E) 2-methylhexanoic acid

13. The structures below are .  (A) not isomers (B) conformational isomers (C) structural isomers (D) cis-trans isomers (E) both B and D

14. The Hell-Volhard-Zelinsky reaction involves . (A) the α-bromination of carboxylic acids (B) the α-bromination of ketones (C) the bromination of alcohols (D) the oxidation of aldehydes to acids (E) none of the above

15. When indole is treated with bromine in dioxane at 0o C, the major organic product is . (A) 2-bromoindole (B) 3-bromoindole (C) 4-bromoindole (D) 5-bromoindole (E) 6-bromoindole

16. Which compound has a 1 H NMR spectrum consisting of the following peaks: 0.9 (6H, d), 1.0 (3H, t), 2.2 (2H, q), and 4.0 (1H, septet)? 

17. How many distinct alkene products are possible when the alkyl iodide below undergoes E2 elimination?  (A) 1 (B) 2 (C) 3 (D) 4 (E) 5

18. Which of the following describes the compound below?  (A) bridged bicyclic (B) fused bicyclic (C) spiro bicyclic (D) bridged tricyclic (E) fused tricyclic