10-27 - 10/27/2010 What is the mechanism of the following...

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Unformatted text preview: 10/27/2010 What is the mechanism of the following reaction? A. E1 or B. E2? What is the major product of the following reaction? A O H R O H R O H R O H R O H R O H R B Br Br Br Br Br Br anti co-planar transition state anti co-planar transition state What is the major product of the following reaction? Why is the less stable alkene the major product? A B What is the most stable conformation of the above bromocyclohexane derivative? H CH3 H H H Br Why is the less stable alkene the major product? H CH3 H H H Br CH3 Br What is the mechanism of this reaction, A. E1 or B. E2? CH3 or B anti periplanar transition state energy E R O C C H H H C H 6 O C H reaction H 1 10/27/2010 What is the product of the following reaction? CH3 or What is the product of the following reaction? B H CH3 H H H H CH3 H H H CH3 H H H H CH3 H H 7 8 9 10 Which of the following alcohols reacts faster? Choose the major product of the following reaction. H 3C CH3 OH H H 3C CH3 CH3 CH 3 A B A CH3 CH3 H CH3 H O H H H H 3C CH3 B CH3 CH 3 H H H 3C 2° 3° 1,2-shift 11 less stable more stable 12 2 10/27/2010 Propose a mechanism for the following reaction. Propose Propose a mechanism for the following reaction. H D Cl H3C H O CH3 B H A Which bond participates in the rearrangement? C Use Use your quiz/workshop form for your answers 1,2-shift less stable more stable 14 Propose a mechanism for the following reaction. Are carbocation rearrangements important in chemistry? H H3C H O CH3 H There will be a carbocation rearrangement question on Exam 2!!! less stable more stable 15 16 1,2-shift Alkynes: Catalytic Hydrogenation, review. H C R1 C R2 H catalytic hydrogenation H H syn addition produces the cis or Z-alkene H H HC H3C C H H CH3 H H H 17 palladium catalyst 18 3 10/27/2010 catalytic hydrogenation H H catalytic hydrogenation H H H CH3 H C H3 H CH3 3 C H H H H HC H3C C C H H H H H H H HC H3C H H H palladium catalyst 19 palladium catalyst 20 catalytic hydrogenation H H catalytic hydrogenation H H H CH3 C H H C H3 C H H H HC H3C H H H H H HC H3C H H H palladium catalyst 21 palladium catalyst 22 catalytic hydrogenation H H catalytic hydrogenation H H H CH3 C H H C H3 C H H H HC H2C H H H H H H HC H2C H H H palladium catalyst 23 palladium catalyst 24 4 10/27/2010 The rearrangement of the following alcohol proceeds to give the product show. A. true B. false 1,2-shift less stable more stable 26 What is the mechanism for this reaction? Which bond would be involved in a 1,2-shift (carbocation rearrangement)? H O H H H O H B A C H 1,2-shift less stable more stable 27 1,2-shift less stable more stable 28 Which of the following 1,2-shifts gives the most stable cation? H O H B A B H C C H A H H 29 5 ...
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This note was uploaded on 12/05/2010 for the course CHE 321 taught by Professor Fowler/sampson during the Fall '08 term at SUNY Stony Brook.

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