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Exam 2 Answers - CHM 2220 Organic Chemistry 2220 Winter...

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Unformatted text preview: CHM 2220 Organic Chemistry 2220 Winter Term 2008 1. Propose a synthesis of 0-selinene, a member of a very common family of sesquiterpenes, beginning with the alcohol shown below. Use a nitrite in your synthesis. Make sure to illustrate the correct stereochemistry (ie. Think about a double inversion). 15 PTS CH CH ? —D- H OH H CH2 H26 H20 CH3 B-Selinene 50g; KCA/ u I) Man/Iggy— :‘oH ’— SW‘CI > M!) H30 2. Identify the reagents appropriate for the following synthesis (put reagents on top of arrows) Show the mechanism for the transformation of 2 —» 3. 15 Points @iifimxgi 1 2 3 Answer: 0 Mechanism: K (I\ HO O o H ... k we; K ._-——7 3. The compound shown was subjected to the following series of reactions to give a product having the molecular formula CQHQCIO3. What is the product? Show the mechanism for the hydrolysis of a nitrile. 15 Points 0 0 H 1- LiA|H4 300i2 NaCN 1. KOH 1. LiAIH4 < , ,. .__.. _._... —-a- 09HQCIO3 0 cr 2. H2O DMSO 2. H30+ 2.H20 Answer: 0 “ab/0H <0 I ,, o 4. Illustrate the product X for the reaction given below. 5 Points 0" 1. MeMgl X F33 2. H30+, heat Answer: X i? a 5. Outline a reasonable mechanism for the following reaction. 10 Points spontaneous HzN S 0 Answer: Mechanism: 6. Give the product Y for the following transformation and outline a detailed mechanism for its formation. 20 Points KOH methanol heat Answer: woo E 7/ Mechanism. 6) Midat/ M7§MG egg flat mfg?“ MW ggfkm ETC @315“ gig}; +116) 1L “HEB Grief Mflcuézo idemdfm £310 %@a 4 Ho; c whze 7. Identify the stereochemistries of carbon a in the following reaction sequence given that the starting chiral reagent 1 has the (R) configuration. Circle the correct answer. 10 Points 0 5 CH3 ——'—"' -———-> Hf?) 5 N a? (5) heat CS) WW I“. [1C chirality of a in ester? chirality of a in alcohol? ac“ 5M SfiWM A) s R Merl firm/'17 We... team/Mme. 0'9 #I’LSWCV' if C) 8. Heating a mixture of 1,3—diphenylacetone and acrolein in trimethylamine gives a product, C18H160. in 53 %yield. The mechanism for product formation is a Michael addition followed by an intramolecular Aldol condensation. Circle the product of the following reaction. 10 Points N(CH3)3 0 o PhEéEjPh +® W o o o CHO Phfi/P“ Iii/P" Phxciph firm Ph CH3 Ph A) B) C) D) ”(16% 56 a é'flWéfl/CO/ f/IZ/ é/c of 3/64/5076 7‘ 3"“64/é7475 9: 6/2ch #jQfi .5) WW) (@,@@) ...
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