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1 Chemistry 220b, Section 1 Exam 2 (100 pts) Thursday, ebruary 26, 2015 Chapters 13, ame Write and sign the VU onor Pledge: I pledge on my honor that I have neither given nor received unauthorized aid on this examination I. M. onest signature This exam is closed book and closed notes TE: It is difficult for me to give you partial credit if you do not show your work! eatness counts Stereochemistry counts are indicated Good Luck!!
2 page 2 of Multiple Choice. Choose the best answer for each of the following questions. (60 pts) 1. Which structure is most consistent with the following 1 MR spectrum? 2. Which structure is most consistent with the following IR spectrum? a) b) c) d) C 3 3. What is the product of the following reaction? 2
3 page 3 of 8 4. What is the product of the following reaction? 2 5. What is the product of the following reaction? C 2 C 3 3 C-MgBr (excess) then 3 C 2 C 3 C 2 C 3 6. What is the product from the following reaction? ac 3 Cl 7. What is the product from the following reaction? 8. What is the best reagent for the following reaction? a) 2 2, K, 2 c) 2, Pd/C b) LiAl 4, T, then 3 d),
4 page 4 of 8 9. Which combination of reactants will give (E)-3-methyl-3-hexene as the product? a) Ph 3 P b) Ph 3 P (2 equivalents) c) Br Ph 3 P d) all of the above; i.e., a, b, and c will all afford (E)-3-methyl-3-hexene 10. What is the best reagent for the conversion of a primary amide to a nitrile? 2 C a) P 4 10, heat b) 3, heat c) 2, Pd/C d) ac, then Which reaction or reaction sequence does not affords phenylacetic acid? a) Br C 3 b) Cr C 2 Cl 2 c) Br Mg(0), T C 2 3 d) none of the above; i.e., a, b, and c are all afford phenylacetic acid 12. What is the order of reactivity, from most reactive to least reactive, for the following reaction? 3 C X 3 C C 3 3 C X X=, Cl, 2 CC 3, C 3 a) 3 C 3 C Cl 3 C C 3 3 C C 3 b) 3 C Cl 3 C C 3 3 C C 3 3 C c) 3 C Cl 3 C C 3 3 C C 3 3 C d) 3 C C 3 3 C Cl 3 C C 3 3 C
5 page 5 of Arrange the following carboxylic acids from the highest pk a value to lowest pk a value. a) b) c) d) 14. Which structure is an intermediate in the saponification of an ester? C 3 a a 3C a) b) c) d) C 3 C 3 C 3 C Which structure is not an intermediate in the formation of a ketal? 2
6 page 6 of The following transformations cannot be done in a single step. Complete the following by providing the correct reagents and the structure of the intermediate. (18 pts) 3-hexyne B 2 6, T; then 2 2, a, 2 Ph 3 P=C 2 Br ac C 3 C - MgBr, T then Give a complete, stepwise mechanism for the acid-catalyzed reaction of propionic acid and methanol to afford methyl propionate. (12 pts) A 3 C 3 C :A A 2 :A 3 C 3 C C 3 C 3
7 page 7 of A molecule with the formula C12172 has the IR, 1 and 13C MR spectra shown below. Provide a structure that is consistent with the data. Please circle your final answer. (10 pts) - X 2C-C 3 C= ~1660 cm-1 amide, possibly conjugated. X 2C-2C-C 3 p-disubstituted benzene Amide - 13 C MR: δ 168.1, 154.2, 132.5, 125.8, 114.5, 64.6, 41.5, 23.1, 14.8, C MR: δ : C=, ester, acid, amide (acid is eliminated since there is no in IR)
8 page 8 of 8 Problem 1-15: (60 pts) 16: (18 pts) 17: (12 pts) 18: (10 pts) Total out of 100:
I pledge my honor that I have neither given nor received aid on this examination
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