308_Exam 2_Spring 2023-V1-KEY-Canvas

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Rutgers University *

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307-308

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Chemistry

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Dec 6, 2023

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First Name __________________________ Last Name ______________________ Section_________ S23 308 E2 I 2 PART I: MULTIPLE-CHOICE QUESTIONS 1-13 Fill in the box that contains the letter corresponding to your answer. For each question, you must completely shade in the correct box – and only one box – to receive credit. A Acceptable B Not acceptable C Not acceptable D Not acceptable E Not acceptable QUESTION 2 (3 pts) Which of the following are not intermediates in the mechanism of the transformation shown? a. 1 only b. 2 only c. 4 only d. 2, 3 e. 1, 4 Exam 2 Version 1 QUESTION 1 (3 pts) Select the reactant X that undergoes cyclization to form the acetal shown. No partial credits for other choice No partial credits for other choice
First Name __________________________ Last Name ______________________ Section_________ S23 308 E2 I 3 QUESTION 3 (3 pts) What is the expected major product of the reaction shown? Assume standard workup as appropriate. QUESTION 4 (3 pts) Which is the expected major product of the following reaction sequence? QUESTION 5 (3 pts) Which compound is expected to be most stable in aqueous sodium hydroxide at room temperature? No partial credits for other choice No partial credits for other choice No partial credits for other choice
First Name __________________________ Last Name ______________________ Section_________ S23 308 E2 I 4 QUESTION 6 (3 pts) Which of the following ( 1-4 ) is the reactive intermediate in nucleophilic aromatic substitution of 1-chloro-4-nitrobenzene with sodium methoxide? A 1 only B 2 only C 3 only D 4 only E None of the other answers is correct. QUESTION 7 (3 pts) Each of the following carbonyl compounds ( A , B , and C ) reacts with water to give corresponding hydrate ( G ) as shown below. Which of the following statements is correct? A. The reaction can occur under acid catalysis only. B. Compound A has the least amount of hydrate formed at equilibrium. C. Compound C has the greatest amount of hydrate formed at equilibrium. D. The reaction can occur under base catalysis only. E. Compound B has the greatest amount of hydrate formed at equilibrium. No partial credits for other choice No partial credits for other choice
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First Name __________________________ Last Name ______________________ Section_________ S23 308 E2 I 5 QUESTION 8 (3 pts) Which structure ( A - E ) corresponds to the b -pyranose form of the monosaccharide shown in the box? (3 pts) QUESTION 9 (3 pts) Which structure ( A to E ) represents the expected major product of the reaction shown below? Assume standard workup as appropriate. No partial credits for other choice No partial credits for other choice
First Name __________________________ Last Name ______________________ Section_________ S23 308 E2 I 6 QUESTION 10 (3 pts) Which of the following, if any, will give a carboxylic acid as the expected major product after standard workup, as appropriate? A. Only (i) B. (i) and (ii) C. None D. (i) and (iii) E. (ii) and (iii) QUESTION 11 (3 pts) Which carbohydrate will give NO reaction? A. Only (i) B. Only (ii) C. (i) and (ii) D. (i) and (iii) E. (ii) and (iii) HO CrO 3 , CH 2 Cl 2 pyridine HO KMnO 4 , H 2 O, Δ O K 2 Cr 2 O 7 H 3 O + (i) (ii) (iii) O H H OH OH CH 2 OH HOH 2 C OH H NaBH 4 EtOH O H OH H OH OCH 2 CH 3 HOH 2 C H H Ag(I) EtOH O H H OH OH OH H HOH 2 C HO H NaBH 4 EtOH (i) (ii) (iii) No partial credits for other choice No partial credits for other choice
First Name __________________________ Last Name ______________________ Section_________ S23 308 E2 I 7 QUESTION 12 (3 pts) Which is NOT part of the mechanism for the reaction shown? A B C D E QUESTION 13 (3 pts) Which reaction coordinate diagram (A-E) is most consistent with the expected mechanism of the reaction shown (1)? O O O H 3 O + , Δ HO OH OH O HO H OH 2 O HO OH O HO O O H OH 2 HO No partial credits for other choice No partial credits for other choice
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First Name __________________________ Last Name ______________________ Section_________ S23 308 E2 I 8 PART II. OPEN-ANSWER QUESTIONS 14-25: All open answers must be written neatly and legibly inside the indicated boxes. Only answers inside the boxes will be graded. Circles, squares, and any other drawing have to be clear and complete. Unclear and incomplete answers will not receive credit. QUESTION 14 (6 pts) Circle the statement or statements (A-E) that is/are TRUE for the major organic product isolated from the reaction below? [Hint: A water molecule (H 2 O) is lost.] A. 1 H NMR spectrum includes 2 singlet peaks. B. 1 H NMR spectrum includes 4 distinct signals. C. 13 C NMR spectrum includes 5 distinct signals. D. IR spectrum includes a broad band in the 2500–3500 cm -1 region. E. IR spectrum includes a band near 1700 cm -1 QUESTION 15 (5 pts) Rank the given compounds in increasing reactivity towards nucleophilic acyl substitution (least reactive to most reactive). OH O H 2 SO 4 , Δ HO < < < < e d b a c 2 pts 2 pts 2 pts 1 pt for each letter in correct position Question 16 (4 pts) Circle the two major products expected of the reaction shown below. 2 pts 2 pts 6 pts for circling three correct ones. 4 pts for Circling the three correct and one wrong answers. 0 pt for circling all five.
First Name __________________________ Last Name ______________________ Section_________ S23 308 E2 I 9 QUESTION 17 (6 pts) Design a one-step synthesis of the ester and a three-step synthesis of the ketone. Use reagents a-g only. Assume standard workup as appropriate. Give your answer in the box provided; give only one letter per step; give the letter only. a. NaBH 4 , MeOH b. CF 3 CO 3 H c. Zn(Hg), HCl d. e. CrO 3 , H 2 SO 4 f. LiAlH 4 , THF g. H 3 O + , heat QUESTION 18 (6 pts) Design a three-step synthesis of the ketone product shown below. Use reagents a-f only. Give your answer in the box provided; give only one letter per step; give the letter only. a. , H + b. H 3 O + , heat c. d. f. a d f g a f b 2 pts 2 pts 1 pt 1 pt e. NaBH 4 , CH 3 OH 2 pts 2 pts 2 pts
First Name __________________________ Last Name ______________________ Section_________ S23 308 E2 I 10 QUESTION 19 (4 pts) Use the template to draw the FIRST tetrahedral intermediate formed in the mechanism of the reaction shown. (Ignore stereochemistry.) QUESTION 20 (4 pts) Rank the relative reactivity of I-IV towards nucleophilic substitution. (Least reactive to most reactive). QUESTION 21 (4 pts) Draw the two major organic products, A and B (they are isomers), formed in the reaction shown. Assume standard workup as appropriate. < < < I III IV II 3 pts for showing the correct tetrahedral intermediate 1 pt for showing the positive charge 0 pt for showing any negative charge in the structure 0 pt for showing a tetrahedral intermediate that is not the FIRST formed. 1 pt for each letter in correct position 2 pts 2 pts No partial credit 3 pts No partial credit 3 pts 2 pts if shown as: QUESTION 22 (6 pts) Draw the expected major product in each box for the following two step sequence. Assume standard workup as appropriate. No other partial credits No other partial credits
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First Name __________________________ Last Name ______________________ Section_________ S23 308 E2 I 11 QUESTION 23 (6 pts) Draw the expected major product in each box for the following two-step sequence shown. Assume standard workup as appropriate. QUESTION 25 (4 pts) Draw the expected major lactone product of the reaction shown. Give your answer in the box provided. Only the answer in the box will be graded. Assume standard workup as appropriate. 1. NaNO 2 , HCl 0–5 ºC 2. CuCN, Δ NH 2 HNO 3 , H 2 SO 4 O CF 3 CO 3 H 3 pts No partial credit 3 pts No partial credit 4 pts 2 pts 4 pts 1 pt if shown as 1 pt if shown as: QUESTION 24 (6 pts) Draw the expected major product of the reaction sequence in the box provided. Assume one equivalent of reagent and standard workup, as appropriate. Only the answer in the box will be graded. 2 pts if shown as: No other partial credits No other partial credits