exam 3 - reagents

Question 1

weak bases

Answer 1

• NH3
• methylamine
• pyridine
• NaHCO3

Question 2

weak nucleophiles

Answer 2

• water
• R-OH (alcohols)
• acetic acid (CH3COOH)
• CH3-OH (methanol)
• AgNO3

Question 3

strong nucleophiles

Answer 3

• CN-
• OH-
• R-O-
• Halide ions, in order of strength (Cl-, Br-, I-)
• NH2-
• negatively charged, large

Question 4

strong bases

Answer 4

• (CH3)3CO- K+
• DBU
• tBuO
• DIPEA
• NaOH
• KOH
• LiOH
• Ca(OH)2

Question 5

X2, Cl-I + H2O
X-OH
PhSeCl
NBS, H2O
X2, R2-acetic acid

Answer 5

halogenation (formation of 3 membered ring, attack of nucleophile resulting in trans formation)

• addition through halonium ion intermediate (trans addition)
• halogenation of alkenes (anti addition)

Question 6

peroxyformic acid
peroxyacetic acid
mCPBA

Answer 6

epoxidation

Question 7

KMnO4 + NaOH/H2O
OsO4 + Na2SO4/H2O

Answer 7

dihydroxlation

Question 8

O3 + Zn/H2O/DMS or H2O2

Answer 8

ozonolysis (reductive or oxidative); syn addition; molozonide intermediate

oxidative -> get carboxylic acid (C=O)
reductive -> get aldehydes (R-CH=O)
alkynes -> get two carboxylic acids

*DMS = (CH3)2S

Question 9

Ni
PtO2
Rh
Ru
Pd-C

Answer 9

Hydrogenation (always syn)

Question 10

Pd-CaCO3/Pd-BaSO4 + PbO/Quinoline

Answer 10

hydrogenation + poisoned catalyst
* to go from alkyne to alkene, make metal catalyst
* always Z

Question 11

Na/Li + NH3 (liq)

Answer 11

dissolving metal reduction of alkynes to alkenes
* always E