(d) With reference to the following reaction scheme: O H || H 22 1. Li, NH3, -78 °C BuOH (1 equiv.) 2. NH4CI 23 (i) Explain why only one of the two C=C double bonds in enone 22 is reduced under these reaction conditions. (ii) Draw a curved arrow mechanism for the transformation of 22 into 23.

Which compound is the major product of the reaction sequence shown? (1) SOCE (A) (B) OH OH (2) (CH3);CO Na (CH3);COH (C) (D) O Na Na CI Compound D Compound A Compound C Compound B

19). What is the major organic product of the following reactions? LBCH COOH 2. Pyridine ? (-HB) (4) D C " & & & & &

Draw the product of each of the following reactions. (a) (b) NaN3 KCN ? H20 ? HOCH,CH,OH (c) (d) HCN 1. LIAIH4 ? HOCH,CH,OH ? 2. Hао (e) (f) CH;OH CH;ONa ? H,SO4 ? CH;OH (g) (Һ) CeH,CH,NH, ? 1. CH3LI ? 2. H,00 CH;OH

Draw the major organic product from the reaction sequence provided: Select Draw Rings More // Cl C 1. SOCI2 2. Et,CuLi 3. (a) LIAIH4 (b) H2O OH

22:18 < 29. Draw the structure of the product that is formed (2)-3-methylpent-2-ene is treated with the following reagents: 1) Hg(OAc)2, H₂O; 2) NaBH, HO™ the reaction in the previous questio