3. a) Determine whether the two indicated protons are homotopic, enantiotopic, or diastereotopic in each of the following molecules. i. iii. H H ii. A iv. V. H H to" H

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1. LDA, -78°C 2 CHIẾ 1. NaH 2. 1. LDA, -78°C 2. CH_Br 3. LDA, -78°C 4. CH_Br Br 1. NaH 2. Br

CI OMe 1) NaNH2, NH3 (1) 2) H₂O*

Li O=U M₁C-C H3C CH3 2. H30*

HO OH EtOEt cat H2SO4

Br CH3OH (f) CH3 CH3 CH3 KO'Bu (h) Br 'BuOH Br CI Bu KCN Ph KO'Bu 'BuOH CH3OH

QUESTION 1 Complete the following synthetic transformation by selecung from the list of reagents below Each rangent te labeled with a letter. In the ancwer box, place the order of reagents using capital letters with no spaces. For example, if your synthesis involves using reagent A followed by B, and then C and then D, your answer would be: ABCD. BH3 A Br CrO3, Pyr B SECCEFLEED ? H₂O₂, NaOH с CrO3, Pyr D PCC

Figure 11-5 A. 1) Hg(0Ac)₂, H₂O B. 1) BH 3 C. D. 2) Na B H4 2) H₂O₂, OH, H₂O 2) OH, DMF ) 1) H Br 1) Hg (0Ac) ₂, H₂O H Br → 3) HBr 3) Ts Cl 2) Brz 3) TSCI ) Br H₂ SO4 4) Br¯ 4) HBr

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