Solution:
Final products of the given reactions are provided in square boxes.
Predict the products.
1. TsCl, pyridine SNa OH NaH HBr 2 eq, 0 °C H2SO4 CH3 heat HBr heat 1. PBr3, Et20 2. NaCN NaH OH HBr 0 °C CH3 H2SO4 heat
PCI 1. NaH HBr 2. (CH3)CHBr он SOC PBr3 2 products
1. Predict the product (s) (or no reaction) and reagent(s). (31 pts; no partial point) 1. TsCI, pyridine OH 2. SNa b. OH NaH C. HBr 2 eq, 0 °C d. ОН H2SO4 heat CH3 HBr Он heat f. но 1. PBr3, EtzO 2. NaCN OH NaH OTs h. Он HBr 0°C CH3 H2SO4 heat Он
1. Predict the product(s) (or no reaction) and reagent(s). (31
pts; no partial point)
1. PBr3, Etz0 2. NaCN NaH ཉེ - ༈ ༈ ཙ ཚེ ན HBr 0 °c HzSO4 heat
Predict the product(s) and reagent(s) or if there is no reaction
write NR.
1. TsCl, pyridine 2. SNa NaH HBO 2 eq, 0 °C H2SO4 heat HBT heat OH 1. PBr3, ED 0 2. NaCN NaH 'OTS
Starting Material Conditions OH PBr3 Eto C NaCN OMs DMF Br NaNH DMSO, 20°C 8 hr 1) NaH, DMF, -78°C 2) A ci NaOH
1. Predict the products of the following reactions. CH3 TsCl Pyridine NaCN CH3 PBr3 Pyridine NaCN (1) BH3:THF (2) H2O2,OH H2SO4(cat.) H2O (1) Hg(OAc)2 (2) NaBH/OH 2. Write the mechanism of the following reactions он но он Ph BF3 Ph
РС H2SO4, H20 1. SOC2, EtgN ОН 2. NaOAc I I יא HBr но 0 °C "CHз H2SO4 heat ОН
complete the following reactions with the proper
stereochemistry as need
оCHbb H2SO4 (dilute) OH H2O HBr (conc) но H но heat но но H CHs MCPBA OH Jones (CrO3. H,SO4) H2O, acetone 1. MCPBA OH PCC 2. NaCN 3. Hy0 pyridinium chlorochromate CH2CI2, 25 C 1. MCPBA PCC OH pyridinium chlorochromate 2. HBr Cн-Cl, 25 C NaBH OH Hао 1. DMSO, (COCI)2, -60C 1. LIAIH 2. Et N 2. H,0
оCHbb H2SO4 (dilute) OH H2O HBr (conc) но H но...
Draw the products of each reaction CH3CH2OH a. H2SO4 [1CHH2a b. 2] H20 ok C. HBr [1] NaCN 2] H20 d.