Chemistry 226 Winter 2015 04.08.2015 Exam 4 Version 2 Name__KET Problem 1 (30 pts):___ Problem 2 (14 pts):____ Problem 3 (14 pts):___ Problem 4 (14 pts):___ Problem 5 (14 pts):__ Problem 6 (14 pts): Total (100pts):Chemistry 226 Winter 2015/Exam 4 1 (30 pts ~ 2 pts each) Identify the choice that best completes the statement or answers the question: 1. Which of the following statements is not true? ‘A. Organocuprates compounds react with acyl chlorides and alky! halides. B. Grignard reagents react with carbonyl compounds, carboxylic acids and their derivatives. © Nitrite compounds react with organocuprates and organolithium compounds, D. Excess of Grignard reagents is needed in their reactions with carboxylic acids. 2. Predict the major product of the following reaction: 3) eS : SAA 3.Which reagent would you use to accomplish the following transformation? o Ow — O¢ A. (CHs)2CuLi, then H30* D. 2 equiv. CHsLi, then H30* B. CHsBr, then H30* E.CH:OH and trace of H2S0s € Lequiv. CHeLi, then Hy" EE_avmaristne major o ° 1. LAI, NHCH, te 2.H,0 ° 9 ae NHy H MHC ‘NH, NHCH, A B. ©. v. | ek J D__5. Rank the acid derivatives in order of increasing stability A i i f ‘OPh A, Aw sh 1 n a " A. IsIlcIll ~ _ 6. What is the product of the reaction conditions shown below? HOH heat $ -H,0 ° AHO LAA LOH oi. c. oh a 0 A, N,N-Ethyl, methyl 3-methylbutanamide B._N,N-Ethyl, methyl sec-butanami C. Ethyl, dimethylbutanamide D._N,N-Ethyl, methyl pentanamide Saws 1 ofthe given reagents could accomplish the transformation below? OCH, OH" & \ A. LiAl(OtBu)sH D.DIBAL-H B. H2/Pd/BaSO, E.AandB C.LiAIHS A 9. Which of the following is the correct product of the reaction below? _— °O NH 9 NH LrChemistry 226 Winter 2015/Bxam 4 AL 10. For the series of compounds below rank the most acidic H (hydrogen). The hydrogen atoms to be considered are shown, 9 9 ° a ‘OCH. Ma 4] ee 4 111, Predict the major product ofthe following reaction 9 Bra \ H,0* 12. Which ofthe following is not a product of the hydrolysis of the compound shown? ° oe q ° 9 ° oe OH NH oe on Hy Ne i 13. Which of the following compounds has the highest absorption frequency among the structures below? a Se Aw at A 14, Which is the structure of ethyl acetoacetate? AL i -. -- || 3 oO °Chemistry 226 Winter 2015/Exam 4 5. Which of the following compounds cannot form an enol? A B. c. D. b EXTRA CREDIT. Which of the following compounds is the correct product of the reaction sequence? NaOH i 1 A. B. Cc BD oO fe Oo 3 ° oO oO O° IL (14 pts.) Match the structures with the names: OH 9° °o 7 tee oe a B c D A oO io ey : COOCHs or Ce F G Name Structure Nitrile E B-Ketoester e Ketene BB Lactam : & fe g Enol ‘Acid Anhydride PeracidChemistry 226 Winter 2015/Exam 4 WV. (14pts) 1, (4 pts) Which of the compounds below matches the !H NMR spectrum? Justify your choice. se 1 ( Viper exh to A quartet) { amet Aaet 40 2, ¢ _gutorte®) 2. (2 pts) Name the compound that you selected in 1. ETH PROPAW CATE 3. (6 pts) Provide two different synthetic methods for compound A, starting from propyl chloride (CHCl). Bo, G04 AL ot es. yor tt,€ Mac a) oo Mae oa 4) 4, 0 oe MRA eee =:Chemistry 226 Winter 2015/ixam 4 W. (14 pts) _—1. (6 pts) The reaction shown here involves formation of an enolate. Draw the structures of the enol and enolate for the compound given, ae. OF eo We 2, (8 pts) Draw the mechanism for the reaction shown in 1. Make sure to include arrows, electron pairs, intermediates, and resonance forms. 2 ro) 0Chemistry 226 Winter 2015/Exam 4 Vv. (14pts) Synthesize the compound given below starting from diethyl malonate and acetic acid as your only source of carbon. You can use any inorganic reagent. 2 0 Ho, Aen ° mira lig Dees 7 oA Nd vo ease aoe > fo NoVL (14 pts) Chemistry 226 Winter 2015/Exam 4 Identify the reagents and products, i.e. draw their structures, for the reaction scheme given below: BEE 1. PhLi 2. HyO*/H,0 1.2eq. LDA 2. CH,CH,CI ° 3.6" OH o 9 att 1. CHjONa ‘OCH, 2. Propyl Chloride COOH, ag 2. Brg/CCl,, heat + Bry Ba ee 7» | B