1. The ketone below is reacted with NaBH4. The products formed from this reaction are: i a. The products are a pair of enantiomers, formed as a racemic mixture. b. The products are a pair of diastereomers, formed in unequal amounts. c. The products are a pair of enantiomers, formed in unequal amounts. d. A meso compound is formed. 2. Rank the following carboxylic acid derivatives from least to most reactive in nucleophilic acyl substitution reactions l l u l NR₂ 3. Rank the following compounds from highest to lowest oxidation state at the carbon containing the carbon oxygen bond он i l R OH R R 4. Circle the functional groups that could be reduced with NaBH4 l l R H R R R OH

Choose the major product of the following reaction sequence. e OEt Br₂/H₂O major product Br th Br OH OH OEt A. B. C. D. E. Choose the incorrect statement about the following reactions. 2 H CH₂OH CH3OH SN1 SN1 A. Both reactions proceed through a carbocation intermediate. B. The same mixture of products would be anticipated for both reactions. C. The equatorial chloride is more stable than the axial chloride. D. The rates of both reactions must be identical. E. The addition of iodide ion to the above reaction mixtures will not affect the rate of these reactions. OH Br OH

8. What is the major organic product that results when hept-1-yne is treated with 2 equivalents of HBr? A) 2,3-dibromohept-1-ene B) 2,3-dibromohept-2-ene C) 1,2-dibromoheptane D) 2,2-dibromoheptane E) 1,1-dibromoheptane