C2710-Exam #5 (Katz) Name: Score: Section - Multiple Choice-Choose the BEST answer from the choices given and write the letter for that answer in the space provided. (50 pts) Consider the reaction below to answer questions 1 and 2 3C- C- Cl 2 ~ ethanol 3C- C- + 3C \ C= C2 / 3C A B c 1. Compound B is the A) SN2 product B) SN1 product C) E2 product D) E1 product 2. Compound C is the A) SN2 product B) SN1 product C) E2 product D) E1 product 3. The mechanism involved when reactions with Na is A) SN2 B) SN1 C) E2 D) E1 4. Choose the BEST reagent to accomplish the following transformation 3C-C-.. 3C- C- A) P3 B) 2, uv light C) gas in DMS D) N-bromosuccinimide
5. Choose the BEST reagent to accomplish the following transformation.. C A) Cl gas in DMS B) NaCl in water C) SCl2 in pyridine D) Cl2 and heat 6. dentify the product of the following reaction A) B) C) D) N-bromosuccinimide uv light 7. dentify the product of the following reaction K+ 8. dentify the product of the following reaction Mg, ether A) Mg B) C) D) Mg Mg Mg 9. Consider the following reaction: The reaction would be classified as A) an oxidation B) a reduction C) neither an oxidation nor a reduction a u ~ cr
10. Consider the following reaction: The reaction would be classified as A) an oxidation B) a reduction C) neither an oxidation nor a reduction (f swer:.. (f 11. Consider the following reaction: The reaction would be classified as A) an oxidation B) a reduction C) neither an oxidation nor a reduction C.. C 12. A term used to describe bond breaking so that both electrons of the bond remain with one fragment is A) homolytic bond cleavage B) radical reaction C) heterolytic bond cleavage D) bond polarization 13. A general term for a species which contains an electron rich site which may attack a positive or partially positive site is A) nucleophile B) electrophile C) carbonophile D) carbocation 14. For the following reaction, which is the major product? A) Product A B) Product B C) A and B are formed in equal amounts. A ether ~ ~ + xr ProductA ProductB 15. ncreasing the temperature at which the following reaction is run would increase the percentage of which product relative to the other? A ~ ether A) Product A B) Product B ProductA C) The percentages of A and B would remain the same ~ + xr ProductB
16. Which of the following is the strongest acid? N 2 17. ydroboration/oxidation of alkenes occurs with! A) anti stereochemistry B) syn stereochemistry C) trans stereochemistry D) no stereochemical preference 18. The regioselectivity of hydroboration/oxidation is A) Markovnikov B) anti-markovnikov C) dependent on the solvent D) unrelated to the alkene structure 19. Povidone (Betadine) is an anti-infective polymer with the general structure: Which of the following is the monomer from which this polyethylene is synthesized? CAo CAo +C-C2-C-C2-t:- n N N N 2 N 20. dentify the major product of the following reaction Cr 3, 2 S 4 ("chromic acid')
21. dentify the major product of the following reaction 1) LiAl 4, ether 2) 3 + 22. Choose the BEST systematic name for the following alcohol A) 1-ethyl-2,3,3-trimethyl-1-butanol B) 2-t-butyl-3-pentanol C) 2,2,3-trimethyl-3-hexanol D) 4,5,5-trimethyl-3-hexanol 23. Choose a series of reactions to accomplish the following transformation? A) 1) 2, heat; 2) Na/N2 B) 1) ; 2) tbu-k+ C) 1) 2, 2; 2) 3+ D) 1) NBS, heat; 2) tbu-k+ C 2 C2 C C C 3 24. Choose a series of reactions to accomplish the following transformation C 2 C C 2? A) 1) 2; 2) C2 B) 1) g(ac)2; 2) NaB4 C) 1) B3; 2) 22, Na; 3) PCC D) 1) 2; 2), RR C 2 C 2 C 25. Choose a series of reactions to accomplish the following transformation A) 1) -C C-Na+; 2) 3 B) 1) Cr3, 2S4; 2) C) 1) SCl2 in pyridine; 2) D) 1) Mg; 2) 3+ C 2 C? C 2 C C 3
Section - Draw correct structures corresponding to the following systematic names (10 pts) 26. 3-ethyl-4-bromo-5,5-dimethyl-2-heptanol 27. 4-bromo-2-ethyl-phenol Section - Give correct systematic names corresponding to the following structures (10 pts) 28. F 29.