-NH2 PCC, CH2Cl2 NaBH CN OH 8 Br 1. 3 equiv. 12 4 equiv. NaOH 1. LiAlH4 2. H2O 2. H30* 9 10 2 equiv. (CH3)2NH 1. LiAIH 2. H20 11 12 H2O 1. CH,MgCI 2. H30 13 14
Draw out each step of the reaction.
OH 1) PCC CH2Cl2 2) MeMgBrEt20 3) PCC CH2Cl2 4) Br2 HBr 5) P(OME)3 6) NaH + aldehyde from step 1
Problem 3 Draw the product from each reaction shown below. OH PCC CH2CL2 - ОН PCC CH2Cl2 NaBH4 EtOH OH 1) LIAIH, Et, 2) H30*
Determine the product of the following reaction. PCC (excess) OH CH2Cl2 OH OH & oni ОН
(1) Show the product of each alcohol oxidation reaction below: OH Croz H30", acetone PCC CH2Cl2 OH Cr₂O, OH H.SO 4, H2O PCC HO CH2Cl2 Nag H2S04, H20 (2) Propose an efficient synthesis for each transformation below mocow OH НО? .name مل.بلو HO / تم.-م" (E) Ph amion e no (F) OMe
HO A) -CH OH PCC, excess CH2Cl2 B) 1) O 2) (CH3), 15) Rank the following compounds in the decreasing order of reactivity towards nucleophilic addition reaction? 3 Pt ! H Most Reactive: Least Reactive 16) Write the reagents for the following transformations? 6 Pt مر 8 B) 0 OH C)
Select (more than one) steps
OH PCC NaBHA CH3OH 1. MgBr CH2Cl2 EtOH H 2. H H2 OH HO HCN DCC KCN
Draw the major organic product of the reaction shown below. -OH pyridinium chlorochromate (PCC) CH2Cl2 • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. ChemDoodle
ОН PCC F) ОН CH2Cl2
provide the major product in the following reaction
NH2 NaBH3CN a. NaNg, EtOH b. H20, A ОН 1. SOCI2, pyridine 2. NaN3, DMF 3. LIAIH4, Et20