33. Which of the following compounds will react with methyl vinyl ketone in a Robinson annulation to generate the cyclic enone below? 
(A) 1-pentene
(B) cyclohexanone
(C) 2-pentanone
(D) pentanal
(E) None of the above

29. Which of the following statements regarding these three compounds is incorrect? (A) I can be converted to III using methanol and catalytic amounts of H2SO4. (B) I can be converted to II using acetic acid and catalytic amounts of H2SO4. (C) II can be produced from I by reaction with acetic anhydride. (D) II and I both will react with sodium bicarbonate to evolve carbon dioxide. (E) II and III are both esters.

30. The acetoacetic ester synthesis, shown below, can be used to prepare 5-methyl-2-hexanone. Which one of the following alkyl bromides would be used in the synthesis? (A) (CH3)2CHBr (B) (CH3)2CHCH2Br (C) (CH3)2CHCH2CH2Br (D) CH3CH2CHBrCH3 (E) (CH3)2CBrCH3

31. Choose the major product of the following reaction. (A) (B) (C)  (D) (E)

32. Rank the following molecules in order of increasing relative rate of SN1 solvolysis with methanol and heat (slowest to fastest reacting).(A) III<II<IV<I<V (B) II<III<IV<I<V (C) I<IV<III<II<V(D) II<III<IV<V<I (E) I<II<V<IV<III 

34. Provide the structure of the major organic product in the reaction below. (A)(B)(C)(D)(E)

35. The product of the following reaction immediately undergoes a dimerization at room temperature. What is the structure of the dimer? (A) (B) (C) (D) (E)

36. For the following multistep synthesis, choose the best reaction conditions to give the desired product? (A) (i) HBr, (ii) O3 followed by Zn/H+ , (iii) Li/NH3 (B) (i) NaNH2/NH3 followed by CH3CH2I, (ii) Lindlar’s catalyst/H2, (iii) OsO4 followed by NaHSO3 (C) (i) H2/Pd/C (1 equivalent), (ii) NaNH2/NH3 followed by CH3CH2Br, (iii) KMnO4/H2O (D) (i) HgSO4/H2O/H2SO4, (ii) Lindlar’s catalyst/H2, (iii) OsO4 followed by NaHSO3 (E) (i) Lindlar’s catalyst/ H2, (ii) NaNH2/NH3 followed by CH3CH2Br, (iii) OsO4 followed by NaHSO3

37. Which sequence of steps below describes the best synthesis of 5-oxohexanoic acid starting with 1-methylcyclopentan-1-ol? (A) 1. Conc. KMnO4; 2. Dry gaseous HBr; 3. Mg/ether; 4. CO2 (B) 1. H2SO4 and heat; 2. Conc. KMnO4 (C) 1. Conc. KMnO4; 2. CH3MgBr/ ether; 3. H3O+ (D) 1. H2SO4 and heat; 2. O3; 3. (CH3) 2S; 4. PCC (E) 1. H2SO4 and heat; 2. Conc. KMnO4; 3. LiAlH4; 4. H3O+

38. Which of the following amines could be formed by reduction of an amide? (I) benzylamine (II) isopropylamine (III) aniline (IV) triethylamine (A) I (B) III & IV (C) I & IV (D) II & III (E) I, III & IV

39. What is the major product of the following reaction? (A) I (B) II (C) III (D) IV (E) V