Chem 255 Exam3 Answers

Chem 255 Exam3 Answers - Chemistry 255 - Fall 2000 Exam 111...

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Unformatted text preview: Chemistry 255 - Fall 2000 Exam 111 Name: 5 Please read each question carefully and write your answers in ink (blue or black only). 1. Please provide the IUPAC name for the following molecules. (15 pts) 5 69:12 Q 3) 2. Draw the structures of the 2 possible constitutional isomers for an alkyne with the molecular formula C4H6. Provide the IUPAC names for the 2 isomers (20 pts) 3. Explain briefly and clearly why treatment of 1-propanol with sodium bromide fails to give l-bromopropane, but treatment with PBr3 succeeds? Use structures and mechanisms to support your answer. (15 pts) I .. I e B r 9 .@\ Rakdum P: =10£$ V104" occur LCM eOH .lS ’ ac rpoor‘ lam/{ms 8’00?) WW I,» I_3_ +exz. altokd ‘15 (.2an a Luv/{+03 W leak/{NS W0 '0. 4. Arrange the following species from best leaving group (A) to worst leaving group (C). Account briefly for why A is a better leaving group than B. (10 pts) Br' I- ~‘s HO' "L- > (- > HO 5. Circle the elimination product that you think will most likely be formed reaction. Provide a mechanistic rationale (mechanism with a brief desc answer. (15 pts) 1' 6. Provide the product(s) of the following reaction. Circle the the reaction proceeded by, Br Reason#l: 2° / . \ , Reason#2: V“? M bM/muf/Q‘Q‘DFW /® Q/hmt UV: IS mechanism type(s) that you beli am support this answer with two different, brief reasons. (20 pts) in the following ription) to support your 9‘ will also /\ acadvf' m. opposiie $79!“ {glam Sm PM I/ B 3 \ ’/ in. s evil. CV6 13) heat b) 9. Please provide the product that will be produced in the following reactions (15 pts): a) MgBr - H20 b) ( 3 1) 03 2) S(CH3)2 H c) H2 Pd 10. Propose a synthesis of A starting from B. Show all reagents, starting materials and products (will be more than one step — two steps would be best). (15 pts) \/\\/\/\ A _ product B - starting material 13. r @ @ gr MAN H 7.. ’ CQ r o K 9M 0M _ \ Q 9‘ 5% V bf.er /// EXTRA CRED (5 pts): ' Circle the compou ow that would have the lowest boiling point. W ) WOH WOH ...
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Chem 255 Exam3 Answers - Chemistry 255 - Fall 2000 Exam 111...

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