Assignment_3_Rxns_of_alkenes_Answers

Assignment_3_Rxns_of_alkenes_Answers - CHM 2120 Assignment...

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CHM 2120 - Assignment 3 - ANSWERS In this assignment: - Electrophilic addition reactions - Radical substitution reactions - Anti-Markovnikov addition to alkenes - Syntheses Note : Some questions were taken directly from CHM1321 assignments. You can choose to review your notes from last year or repeat the assignments. 1. Provide a mechanism for the following transformations (only product is required for h and i): H 2 SO 4 H 2 O +H B r a) b) +H C l c) 1-methylcyclohexene +H C l d) +H B r e) 1-methylcyclopentene H H Br Br H H Cl Cl H Cl Cl H H Br Br Br Br H H H 2 O OH H H 2 O OH
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Assignment 3 Answers 2 H 3 PO 4 H 2 O HO H 3 PO 4 AIBN Δ AIBN Δ f) g) h) +H C l i) +H B r Ph H Ph H H 2 O Ph OH H H 2 O Ph OH HO H HO H O H H H 2 O O NN CN CN CN 2 +N 2 Initiation: NC HC l NC + Cl Propagation Cl Cl HC l Cl + Cl NN CN CN CN 2 +N 2 Initiation: NC HB r NC + Br
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Assignment 3 Answers 3 2. Explain the formation of the major product: O + CH 3 OH H (+) O CH 2 OCH 3 O CH 2 OCH 3 H H Major very minor O H H H add methanol and lose a proton to regenerate the catalyst OR O H H H O H H H Resonance-stabilized carbocation: the transition state leading to this intermediate is lower, and since the generation of the cation is the r.d.s., lower this transition state leads to a faster reaction overall. Not resonance-stabilized
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This note was uploaded on 01/25/2011 for the course CHM 2120 taught by Professor Dr.flynn during the Spring '10 term at University of Ottawa.

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Assignment_3_Rxns_of_alkenes_Answers - CHM 2120 Assignment...

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