Organic Chemistry II KEY February 20, 2013

Transcription

1 rganic Chemistry II KEY February 20, 2013 Exam 1: VERSI C 1. Which of the following compounds could be generated from reaction of Z 3,4 dimethyl 2 pentene with m chloroperbenzoic acid? E C 3 3 C 3 C C 3 3 C C 3 C 3 V b) I & II d) III & IV e) I 2. Treatment of the diol below with 1 equivalent of Br under kinetic conditions provides a product A. The product then reacts with a to give the final product, B. Which of the following compounds represents product B? C 1 equivalent of Br (kinetic) A a B & II b) IV d) III & IV e) II 1

2 rganic Chemistry II KEY February 20, 2013 Exam 1: VERSI C 3. Rank the compounds below from highest oxidation state to lowest oxidation state (highest > lowest). A V > I > II > III b) IV > II > I > III > II > I > IV d) IV > I > III > II e) I > IV > II > III 4. Which of the following structures represents the conjugate base that would form upon reaction with the compound below with weak base (p= 10)? B 2 b) IV d) II e) III & IV 2 5. Reaction of 1S, 2S methylcyclopentanol with thionyl chloride (SCl 2 ), followed by treatment with sodium methoxide (C 3 a + )will provide: D a) 1R methoxy 2S methylcyclopentane b) 1S chloro 2S methoxycyclopentane c) 1R chloro 2S methylcyclopentane d) 1S methoxy 2S methylcyclopentane e) 1R methoxy 2R methylcyclopentane 2

3 rganic Chemistry II KEY February 20, 2013 Exam 1: VERSI C 6. Which of the following compounds will provide a di substituted alkene as the major thermodynamic product upon reaction with PCl 3, Et 3? C I. C 3 II. C 3 C 3 C 3 b) III c) I & II d) I, II & IV e) III & IV 7. Which of the following reaction energy diagrams represents the reaction of albuterol with one equivalent of Cl? B Albuterol & IV b) IV d) II e) I Energy Energy SM P P SM P P Reaction Progress Reaction Progress Energy Energy SM P P Reaction Progress SM P P Reaction Progress 3

4 rganic Chemistry II KEY February 20, 2013 Exam 1: VERSI C 8. Loxoprofen could be generated from which of the following starting materials upon treatment with Jones reagent? D Starting Material Jones reagent Loxoprofen I. II., II, III & IV b) I, II & IV c) I, II & III d) I & II e) I 9. The major product(s) of the reaction below is (are): A C equivalents of TsCl 2. 2 equivalents of C 3 C 2 2 a) A single stereoisomer b) A mixture of diastereomers c) A mixture of enantiomers d) A mixture of positional isomers e) b & d 10. Which of the following alkene starting materials will give 2,4 dimethylcyclopentanol as the only major product upon reaction with either 3 + or 1. B , a? Credit given for all answers I. 1,3 dimethylcyclopentene II. 1,4 dimethylcyclopentene 3,5 dimethylcyclopentene 2,3 dimethylcyclopentene & II b) II & III d) III & IV e) II 4

5 rganic Chemistry II KEY February 20, 2013 Exam 1: VERSI C 11. Which pair of starting materials could be used to prepare the ether functional group of duloxetine through a Williamson ether synthesis? A I. S Cl + a S C 3 II. S + Cl a C 3 C 3 Duloxetine S + a C 3 Cl S + a V b) I & II c) I & III d) III e) I Cl C Which of the following compounds will provide a single product that contains three aldehydes and one ketone when reacted with excess reagent ( Zn, Cl) in an ozonolysis reaction? C b) II & IV d) II & III e) IV 5

6 rganic Chemistry II KEY February 20, 2013 Exam 1: VERSI C 13. Which of the following ewman projections represents the conformation that leads to the major thermodynamic product of the reaction outlined below? B C 3 C 3 PCl 3 pyridine b) III c) I & III d) II e) I, III & IV C 3 3 C C 3 C 3 C 3 C 3 3 C C Treatment of retronecine with PCC in C 2 Cl 2 will provide: B Retronecine & II b) III c) II d) IV e) one of these PC C, C 2 Cl 2 I. II. 6

7 rganic Chemistry II KEY February 20, 2013 Exam 1: VERSI C 15. The reaction below will provide: A cold, dilute KMn 4 a) A mixture of diastereomers b) A mixture of positional isomers c) A single stereoisomer d) A racemic mixture e) a & b 16. Which of the following methods could be used to prepare ( ) isomenthol? (ote: ther major products may form along with ( ) isomenthol). B C 3 I. C 3 II. C 3 1. B 3 a , a Br ( ) isomenthol C 3 C 3 & II b) I c) II d) I & III e) IV cold, dilute KMn The major kinetic product(s) of the reaction of α terpinol with 3 P 4 is (are): D 3 P 4 II b) IV c) I, II & III d) I & II e) II & III terpinol 7

8 rganic Chemistry II KEY February 20, 2013 Exam 1: VERSI C 18. Reaction of shikimic acid with aqueous acid ( 3 + ) gives quinic acid as the major kinetic product. Which of the following chair conformations represents quinic acid? E Shikimic Acid 3 + Quinic acid & III b) I & II d) IV e) I C 2 C 2 C 2 C In the laboratory the set of results given below were obtained when conducting the following tests: Jones, Iodoform, Bromine/Water, Lucas and Permaganate. Which of the following compounds are consistent with these test results? C Test Result Jones Tests + Iodoform Test Bromine/Water + Lucas Test b) II & IV c) I & III d) III e) IV KMn 4 + 8

9 rganic Chemistry II KEY February 20, 2013 Exam 1: VERSI C 20. The mechanism of the reaction below is a (an): A + a) E 1 b) E 2 c) Electrophilic addition d) S 1 e) S Which of the following structures represents an enantiomer of illudin M? C I. II. Illudin M & II b) IV c) II d) III e) I & III 22. Cortisol is a naturally occurring steroid hormone that is released in response to stress and low blood sugar. It contains one primary, one secondary and one tertiary alcohol, two ketones and a tri substituted alkene. Which of the following structures represents cortisol? B I. II. b) II d) IV e) one of these 9

10 rganic Chemistry II KEY February 20, 2013 Exam 1: VERSI C 23. Which of the following compounds cannot undergo elimination upon activation of the hydroxyl group with either acid or PCl 3 and base? C b) I & II c) II & IV d) I, II, IV e) III & IV 24. Match the reaction species (labeled as A, B, C, etc ) with the correct structure (I VI) provided. Reaction species may be reaction intermediates or products. Assume no rearrangements occur. E A SM 2 S 4 B SM + + Starting Material (SM) C D E F (Major thermodynamic product) 2 V. VI. a) A = III B =IV C=VI D =II E = I F =V b) A = III B =II C=IV D =VI E = I F =V c) A = III B =IV C=II D =VI E = V F =I d) A = II B =III C=VI D =IV E = I F =V e) A = III B =IV C=II D =VI E = I F =V 10

11 rganic Chemistry II KEY February 20, 2013 Exam 1: VERSI C 25. Which of the following compounds can undergo intramolecular hydrogen bonding? D I. II. Chorismic Acid Fudecalone & II b) III & IV c) I, II & III d) I, III & IV e) I, II, III & IV Levabuterol Entecavir 2 11