10-26 - 10/26/2009 Choose the major product of the...

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Unformatted text preview: 10/26/2009 Choose the major product of the following reaction. H 3C CH3 OH H H 3C CH3 CH3 CH 3 Propose a mechanism for the following reaction. A CH3 H O H H H H 3C CH3 B CH3 CH 3 H H3C H H 3C H O CH3 B H A Which Which bond participates in the rearrangement? C 2° 3° 1,2-shift less stable more stable 1 1,2-shift less stable more stable 2 Propose a mechanism for the following reaction. The rearrangement of the following alcohol proceeds to give the product show. H H3C H O CH3 H A. A. Very sure this is true B. B. Somewhat sure this is true C. Maybe this is true D. Maybe this is false E. Somewhat sure this is false F. Very sure this is false 1,2-shift less stable more stable 3 1,2-shift less stable more stable 4 The rearrangement of the following alcohol proceeds to give the product show. Rearrangement involving bond A does not give a 3° cation. A. true B. false H O H H H H O H B A? B H C? H A 1,2-shift less stable more stable 5 6 1 10/26/2009 Rearrangement involving bond C does not give a stable 3° cation. A. true B. false Alkynes: Catalytic Hydrogenation, review. syn addition produces the cis or Z-alkene B H H O A? B H C C? H A H H 7 8 catalytic hydrogenation H H catalytic hydrogenation H H H H HC H3C C H H CH3 H H H H H HC H3C C H H CH3 H H H palladium catalyst 9 palladium catalyst 10 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 11 palladium catalyst 12 2 10/26/2009 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 H2C H H H H palladium catalyst 13 palladium catalyst 14 catalytic hydrogenation H H catalytic hydrogenation H Pd C C H Pd H C C H CH3 C H H Predict major product of the following reaction. H H H 70% 30% H H HC H2C palladium catalyst 15 A B 16 If H2 only adds syn how is the trans compound formed? If H2 only adds syn how is the trans compound formed? Predict major product of the following reaction. Predict major product of the following reaction. 70% 30% 70% 30% A B 17 A B 18 3 10/26/2009 The product of the following hydrogenation rotates the plane of polarized light. The following hydrogenation gives only compound A. Naproxene A. A. Very sure this is true B. B. Somewhat sure this is true C. Maybe this is true D. Maybe this is false E. Somewhat sure this is false F. Very sure this is false 19 20 Catalytic hydrogenation of alkynes is a synthesis of both cis alkenes and alkanes. How are alkynes prepared? Br C R1 strong base C R2 H E2 strong base Cl C R1 E2 R2 C H 21 22 Alkynes can be prepared from either alkenes or carbonyl compounds. How could the following alkyne be prepared from bromobenzene and reactants containing 4 carbons or less? 23 24 4 10/26/2009 Choose the reaction sequence that could not be used to prepare the alkyne. How could the following alkyne be prepared from bromobenzene and reactants containing 4 carbons or less? A B C D 25 26 How could the following alkyne be prepared from bromobenzene and reactants containing 4 carbons or less? How can the following alkyne be prepared from bromobenzene and reactants containing 4 carbons or less? H 1. NH2 Br 2. 27 28 30 5 ...
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This note was uploaded on 12/25/2009 for the course CHE 320 taught by Professor Ff during the Spring '09 term at SUNY Stony Brook.

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