CHM+112B+Review

CHM+112B+Review - CHM112B FinalReviewSession 1. Me O Br O...

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CHM 112B Final Review Session 1. 2. 3. 4. MeO Br O Me O Me H H H MeO plus any other reagent heat O O Me MeO O O Me MeO Me Me CO 2 Me CO 2 Me heat Me Me CO 2 Me CO 2 Me Justify relative stereochemistry of methyl groups MeO N N N O N OH O NH 2 O HO H 2 N
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5. 6. Cl O O O N O O O 2 N O N H C A B Propose a synthesis for C starting from benzene, using A , B , and any other common organic laboratory chemicals. Bonus: show the mechanism for each step. O Ph Ph Me H O tBu H O Ph tBu OH O Ph tBu Me OH O Ph tBu Me OH O Ph tBu Me OH LDA + a) Which of the four compounds shown are likely to result from the following reaction if LDA generates the E-enolate? Circle all possibilities. b) Rationalize your answer by drawing a transition state structure for the formaiton of each of the compounds you circled above. E-enolate: OLi Ph Ph Me Ph Me Ph Ph Ph c) What is the stereochemical relationship amongst the products you selected?
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7. 8. Me OH NH 2 1) TsCl, Et 3 N 2) N O O I B(OH) 2 Br Pd(PPh 3 ) 4 benzene/EtOH aq Na 2 CO 3 , refux 1. NaNO 2 , CuBr, H 2 SO 4 , AcOH aq HBr rt to 80 ˚C 2. Protecting group switch: -OTs to -OMOM (N-iodosuccinimide)
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This note was uploaded on 09/20/2011 for the course CHEMISTRY 120 taught by Professor Head-gordon during the Spring '11 term at ASU.

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CHM+112B+Review - CHM112B FinalReviewSession 1. Me O Br O...

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