CHEM 334 EXAM 2 REAGENTS QUESTIONS AND CORRECT DETAILED ANSWERS (VERIFIED ANSWERS) ALREADY GRADED A+

CHEM 334 EXAM 2 REAGENTS QUESTIONS AND CORRECT
DETAILED ANSWERS (VERIFIED ANSWERS) ALREADY
GRADED A+
weak oxidizing agents, oxidizes alcohols to ketones or aldehydes
Ans✓✓✓PCC, NaOCl/TEMPO or AcOH, Swern, DMP


cleaves double bond into 2 ketones or ketone and aldehyde Ans✓✓✓1)
O3 -78 degrees Celsius
2) (CH3)2S


add H and OH across triple bond Markovnikov, keto enol
tautomerization Ans✓✓✓Hg2+,H2SO4/H2O


add H and OH across triple bond anti Markovnikov, keto enol
tautomerization Ans✓✓✓1)Sia2BH 2)H2O2, NaOH


Nitrile/ester to aldehyde
ketone/aldehyde to alcohol Ans✓✓✓(i-Bu)2AlH, H3O+ or DIBAL-H,
H3O+


reduces to aldehyde OR all the way to alcohol Ans✓✓✓LAH with
carboxylic acid


replaces OH with Cl Ans✓✓✓SOCl2

, acyl chloride to aldehyde Ans✓✓✓Li+-AlH(O-t-Bu)3 or H2, Pd,
BaSO4, S


removes LG and adds 1 R, replaces LG with R chain attached to reagent
Ans✓✓✓R2CuLi


reduces ketones and aldehyde to alchols Ans✓✓✓NaBH4


H3O+ or NaOH Ans✓✓✓reagent to 2 OH to ketone


carbonyl to OH and CN Ans✓✓✓KCN or HCN


forms an imine Ans✓✓✓R-NH2/H+


forms an enamine Ans✓✓✓R-NH/H+


forms new carbon to carbon double bond Ans✓✓✓1)Ph3P-R
2) BuLi


oxidizes aldehyde to carboxylic acid Ans✓✓✓Na2CrO7 or
Ag2O/THF,H2O, and CrO3, aq. H2SO4/acetone


replaces carbonyl with 2 H Ans✓✓✓Zn(Hg)/HCl,H2O