Reactions

Question 1

SN1

Answer 1

Unimolecular, Hindered, Protic (needs shell), LG=WB, Nu=S/W

Question 1

SN2

Answer 1

Bimolecular, Unhindered, Aprotic (no shell, LG=WB, Nu=SN

Question 2

Free Radical Initiation

Answer 2

X2 -> hr -> 2 X free radicals

Question 3

Free Radical Propagation

Answer 3

1 Free Radical X and RH

Question 4

Free Radical Termination

Answer 4

2 Free Radicals -> X2, RX, R2

Question 5

Location of Free Radical Substitution

Answer 5

Most substituted

Question 6

Radical Bromination

Answer 6

Slow/Selective

Question 7

Radical Chlorination

Answer 7

Fast/Unstable

Question 8

Combustion Reaction

Answer 8

Alkane + Oxygen -> CO2 + H20 + heat

Question 9

E2

Answer 9

Bimolecular, Hindrance Independent, Bulky Base, Basic, Nu=SB

Question 10

E1

Answer 10

Unimolecular, Protic Solvent, Highly Branched, Good LG, Nu=Weak, Acidic

Question 11

Reduction

Answer 11

Alkene -> H2/Pd/Pt -> Alkane

Question 12

Addition HX

Answer 12

Alkene -> HBr -> Markovnikov

Question 13

Addition X2

Answer 13

Alkene -> X2 -> Anti-Add (Bromonium Ion)

Question 14

Addition H20

Answer 14

Alkene -> H20 -> OH Adds Mark

Question 15

Free-Radical Bromination

Answer 15

Alkene -> Anti-Mark

Question 16

Hydroboration

Answer 16

Alkene -> BH3,H2O2,OH -> Anti-Mark OH add (syn OH/H)

Question 17

Oxidation

Answer 17

Alkene -> Kmno4 (dil) -> 2 OH (syn)

Question 18

Ozonolysis (Zn)

Answer 18

Alkene -> O3/Zn -> Aldehyde/Ketone

Question 19

Ozonolysis (NaBH4)

Answer 19

Alkene -> O3/NaBH4 -> Alcohol

Question 20

Peroxy

Answer 20

Alkene -> mCPBA -> Epoxide

Question 21

Alkyne Synthesis

Answer 21

Dihalogen -> Heat/Base -> Alkyne

Question 22

Alkyne Addition

Answer 22

Alkyne -> n-BuLi/CH3 -> Longer Chain

Question 23

Alkyne -> Alkene (cis)

Answer 23

H2/Pd, Lindlar

Question 24

Alkyne -> Alkene (trans)

Answer 24

NaNH3

Question 25

Hydroboration (Alkyne)

Answer 25

Alkyne -> R2BH/H2O2,OH -> Aldehyde/Ketone

Question 26

Oxidation (Alkynes -> Acids)

Answer 26

Kmno4/H+

Question 27

Aromatic Rule

Answer 27

4n + 2 = # of pi electrons

Question 28

Halogenation (Aromatic)

Answer 28

FeBr3/heat -> Add X

Question 29

Sulfonation (Aromatic)

Answer 29

SO3/H2SO4/heat -> Add SO3H

Question 30

Nitration (Aromatic)

Answer 30

H2SO4/HNO3 -> Add NO2

Question 31

Friedel-Crafts (Aromatic)

Answer 31

AlCl3/CH3COCl -> Add CH3O

Question 32

Electron-Donating Groups

Answer 32

NH2 > NR2 > OH > OR > R

Question 33

Electron-Withdrawing Groups

Answer 33

F > Cl > Br > I NO2 > SO3H > COOH

Question 34

Catalytic Reduction (Aromatic)

Answer 34

H2/Rh/C -> No pi bonds

Question 35

Carboxylic Acid Full Reduction

Answer 35

LAH/H3O+

Question 36

Ketone Reduction

Answer 36

NaBH4/H3O+

Question 37

Phenol Addition

Answer 37

Aromatic-NH2 -> HNO2/H2SO4,H3O+ -> Phenol

Question 38

Elimination (Alcohol)

Answer 38

H2SO4,heat

Question 39

Substitution (Alcohol)

Answer 39

SOCl2

Question 40

Oxidation (Alcohol -> Ketone)

Answer 40

PCC, Na2Cr2O7

Question 41

Oxidation (Alcohol -> COOH)

Answer 41

CrO3, H2SO4/acetone

Question 42

Clemmenson Redox

Answer 42

Carbonyl -> Hg(Zn)/HCl -> No Carbonyl

Question 43

Wolff-Kishner

Answer 43

Carbonyl -> H2NNH2/Base -> No Carbonyl

Question 44

Hydration (Carbonyl)

Answer 44

H2O -> Diol

Question 45

Hemiacetal

Answer 45

1 OR

Question 46

Acetal

Answer 46

2 OR

Question 47

Hydrogen Cyanide

Answer 47

Carbonyl -> CN/H+ -> Add OH/CN

Question 48

Ammonia Addition

Answer 48

Carbonyl -> NH3 -> Ammonia Add

Question 49

Wittig

Answer 49

ylide + Carbonyl -> =CH2