Chem 14D Exam 1. Spring 2012 / Prof. Neil Garg. Friday, April 27, :00 1:50 PM. Page Possible Points Score bonus.
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1 Chem 14D Exam 1 Spring 2012 / Prof. eil Garg Chem 14D Exam 1 P.1 Friday, April 27, :00 1:50 PM General Instructions: This is a standard closed-note exam. Please read each question carefully and write your answer neatly in the space provided using a black blue pen (no pencils!). You may use the back of the pages and page 7 as scrap paper. The use of model sets is allowed. A periodic table is provided on the last page of the exam. Cell phones, calculats, headphones are not permitted. Keep your Student ID card out f ID Check. GD LUCK! Page Possible Points Sce Total bonus bonus PLEASE PRIT & SIG YUR AME BELW T ACKWLEDGE TAT YU WILL ADERE T TE CEM 14D R CDE: n my hon, I will not give receive any unauthized aid on this exam. Print ame / Student ID# Sign ame
2 Chem 14D Exam 1 P.2 1) F each compound shown below, indicate whether the compound is nucleophilic electrophilic at the marked atom (*) by circling your answer. (5 points each) * electrophilic nucleophilic * Ts electrophilic nucleophilic 2) Indicate if each of the following statements are either true false by circling your answer (3 points each) Sodium hydride reduces ketones to secondary alcohols. The first step of an reaction is dissociation. c) I is a better leaving group compared to F. d) 2 is a strong base. e) rganic chemistry is part of your everyday life (e.g., medicine, clothing dyes, studying f 14D) PITS EARED TIS PAGE / 25
3 Chem 14D Exam 1 P.3 3) Predict the maj product f each of the following reactions. Answers without a clear indication of stereochemistry will not be given any credit! (5 points each) a DMF a DMF 4) Provide the necessary reaction conditions (reagents and solvents, consistent with lecture material) needed to accomplish the following transfmations. Please place your answer in the box provided around the reaction arrow. (5 points each) Mg Et 2 Mg PCC C 2 Cl 2 c) ab 4 Et... LiAl 4 Et 2 PITS EARED TIS PAGE / 25
4 Chem 14D Exam 1 P.4 Instructions f questions 5 and 6: F each of the reactions given, circle the reaction pathway that would predominate (,, ) and draw the maj product. Do not draw me than one product. If would occur, circle and draw an X in the product space. 5) (5 points each) Ts benzene heat (draw maj product 'X') atbu tbu (draw maj product 'X') 6) (5 points each) (draw maj product 'X') F 2 (draw maj product 'X') PITS EARED TIS PAGE / 20
5 Chem 14D Exam 1 P.5 7) Draw an arrow-pushing mechanism f the following reaction. You may assume wkup using 2 and please include the mechanism f wkup as part of your solution. (10 points) Li Et 2 Li + wkup Li Instructions f questions 8 10: Follow the individual instructions f each problem below, pertaining to synthesizing the cyclohexene shown below. 8) Provide the necessary reaction conditions (e.g., reagents and solvents, consistent with lecture material) needed to accomplish the following elimination. Please place your answer in the box provided around the reaction arrow. (5 points) Ts benzene heat 9) Consider the 3-D depiction of the compound shown below. Would you expect this substrate to readily undergo elimination if treated with typical reaction conditions? Circle your answer. (5 points) Ts Ts assume the molecule is locked in this confmation elimination? Yes o PITS EARED TIS PAGE / 20
6 Chem 14D Exam 1 P.6 10) Propose a synthetic scheme f the following conversion, using a plausible elimination as one of your synthetic steps. You may use common reagents and solvents, such as the reagents and solvents seen in this exam, problem sets, lectures, and practice tests. It is T necessary to show an arrow-pushing mechanism in your answer. (10 points) Ts Ts a atbu DMF tbu Bonus: Circle the appropriate name and most appropriate description f each of the molecules shown below based on your general knowledge and the material presented in lectures (5 points f having all crect answers; no partial credit). C C 2 ame? ame? Lipit Lipit F F 2 C ame? ame? Lipit Lipit PITS EARED TIS PAGE / 15
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