CHEM 238 BUNDLED ASSESSMENT
QUESTIONS WITH COMPLETE VERIFIED
SOLUTIONS
●● H2SO4 or H3PO4
Answer: Alcohol Dehydration
●● Sn1 Alkylhalide
Answer: Tertiary or Secondary Alcohol and HX
●● Sn2 Alkylhalide
Answer: Primary Alcohol and HX
●● TsCl + Pyridine + X- + DMSO
Answer: Sulfonate Esters into Alkyl Halides
●● SOCl2 + Pyridine
Answer: Chlorination of Alcohols
●● Ph3PBR2 + DMF
Answer: Bromination of Alcohols
, ●● Na2Cr2O7 + H2SO4
Answer: Secondary Alcohol = Ketone
Primary Alcohol = Carboxylic Acid
●● PCC + CH2Cl2
Answer: Primary Alcohol = Aldehyde
●● 1) BH3, THF
2) H2O2, NaOH
*Alcohol added to less substituted carbon*
Answer: Hydroboration Oxidation of Alkenes
●● 1) Hg(OAc)2, H2O
2) NaBH4
*alcohol added to more substituted carbon*
Answer: Oxymercuration Reduction of Alkenes
●● NAD+, Alcohol Dehydrogenase/H2O
Answer: Oxidation of Ethanol, forms acetaldehyde and NADH
●● HNO3 or KMnO4
QUESTIONS WITH COMPLETE VERIFIED
SOLUTIONS
●● H2SO4 or H3PO4
Answer: Alcohol Dehydration
●● Sn1 Alkylhalide
Answer: Tertiary or Secondary Alcohol and HX
●● Sn2 Alkylhalide
Answer: Primary Alcohol and HX
●● TsCl + Pyridine + X- + DMSO
Answer: Sulfonate Esters into Alkyl Halides
●● SOCl2 + Pyridine
Answer: Chlorination of Alcohols
●● Ph3PBR2 + DMF
Answer: Bromination of Alcohols
, ●● Na2Cr2O7 + H2SO4
Answer: Secondary Alcohol = Ketone
Primary Alcohol = Carboxylic Acid
●● PCC + CH2Cl2
Answer: Primary Alcohol = Aldehyde
●● 1) BH3, THF
2) H2O2, NaOH
*Alcohol added to less substituted carbon*
Answer: Hydroboration Oxidation of Alkenes
●● 1) Hg(OAc)2, H2O
2) NaBH4
*alcohol added to more substituted carbon*
Answer: Oxymercuration Reduction of Alkenes
●● NAD+, Alcohol Dehydrogenase/H2O
Answer: Oxidation of Ethanol, forms acetaldehyde and NADH
●● HNO3 or KMnO4