CHEM 334 EXAM 3 QUESTIONS AND CORRECT DETAILED ANSWERS (VERIFIED ANSWERS) ALREADY GRADED A+

CHEM 334 EXAM 3 QUESTIONS AND CORRECT DETAILED
ANSWERS (VERIFIED ANSWERS) ALREADY GRADED A+
CuCl; CuBr; CuCN; KI; H3PO2; H3O+ Ans✓✓✓Replaces N2
+ with Cl/Br/CN/I/H/ or OH


(PH)3P=CH2R Ans✓✓✓=O to =CH2R


H2O2/heat or MCPBA/heat (cope elim) Ans✓✓✓-NR2 group
eliminates down to alkene (Anti-mark)


NaBH3CN Ans✓✓✓-Reduces imines/enamines to amines
-can connect figure at carbonyl groups


HBF4 Ans✓✓✓-N2+ to F


(1) DILBAlH(78°C), (2) H2O Ans✓✓✓Ester/carboxylic acids to
aldehyde


NaBH4/CH3OH Ans✓✓✓-Aldehyde to primary alc
-ketone to secondary alc


Ag2O/THF, H2O (Tollens Reagent) Ans✓✓✓Aldehyde to carboxylic
acid

, NaOCl/TEMPO or PCC Ans✓✓✓Primary alc to aldehyde
Secondary alc to ketone


H2O2 or ArCO3H (cope elim) Ans✓✓✓3° Amine to 3° Amine Oxide


(1) conc. KMnO4, heat (2) H+ Ans✓✓✓-methyl or propane or butyl on
benzene to carboxylic acid
-no reaction with t-butyl


1) BH3THF 2) H2O2/NaOH Ans✓✓✓Anti-markovnikov addition of
OH


1) Hg(OAc)2/H2O 2)NaBH4 Ans✓✓✓Markovnikov addition of OH


1) O3, -78C 2) (CH3)2S Ans✓✓✓oxidative cleavage of alkene


H2, Raney Ni Ans✓✓✓-total reduction of all alkenes
-Ald to 1°OH
-Ket to 2°OH


H2SO4/heat Ans✓✓✓alcohol to alkene