Mechanism Review

Question 1

SN1 Mechanism (Alcohols)

Answer 1

→ Starts with - Tertiary Alcohol
→ Reacts with - HBr and Protic Solvent (CH3CH2OH)
→ PRODUCT = Alkyl Halide

Question 2

SN1 Mechanism (Alkyl Halide)

Answer 2

→ Starts with - Tertiary Alkyl Halide
→ Reacts with - H2O
→ PRODUCT = Alcohol

Question 3

SN2 Mechanism (Alcohol)

Answer 3

→ Starts with - Primary Alcohol
→ Reacts with - HBr and Aprotic Solvent (DMSO, Dimethyl Sulfoxide)
→ PRODUCT = Alkyl Halide

Question 4

SN2 Mechanism (Alkyl Halide)

Answer 4

→ Starts with - Primary Alkyl Halide

→ Reacts with - H2O and DMSO (Dimethyl Sulfoxide) → PRODUCT = Alcohol

Question 5

E1 Mechanism (Alcohol)

Answer 5

→ Starts with - Tertiary Alcohol
→ Reacts with - Strong Acid (H2SO4) and HEAT
→ PRODUCT = Alkene

Question 6

E1 Mechanism (Alkyl Halide)

Answer 6

→ Starts with - Tertiary Alkyl Halide
→ Reacts with - Weak Base (NaOCH2CH3, OHCH2CH3) and HEAT
→ PRODUCT = Alkene

Question 7

E2 Mechanism (Alcohol)

Answer 7

→ Starts with - Primary Alcohol
→ Reacts with - Strong Acid (H2SO4) and HEAT
→ PRODUCT = Alkene

Question 8

E2 Mechanism (Alkyl Halide)

Answer 8

→ Starts with - Primary Alkyl Halide
→ Reacts with - Strong Base (NaOCH2CH3) and HEAT
→ PRODUCT = Alkene

Question 9

Synthesizing Alkynes Via Elimination

Answer 9

→ Starts with - Geminal or Vicinal Dihalides
→ Reacts with - 2NaNH2, NH3 (Internal) OR 3NaNH2, NH3, H2O (External)
→ PRODUCT = Internal OR Alkyne

Question 10

Hydrogenation of Alkynes

Answer 10

→ Starts with - Alkyne
→ Reacts with - 2 Mol H2 with Metal Catalyst (Pt, Pd, Nr, Rh) OR 1 Mol H2 with Lindlar’s Catalyst (Pt, Pd, Nr, Rh) OR Na with NH3
→ PRODUCT = Alkene (CIS or TRANS) OR Alkane

Question 11

Hydrogen Halide Addition of Alkynes

Answer 11

→ Starts with - Alkyne
→ Reacts with - 1 or 2 mol of Hydrogen Halide (ex. HCl)
→ PRODUCT = Alkene or Alkane with Hydrogen Halide

Question 12

Hydration of Alkynes

Answer 12

→ Starts with - Alkyne
→ Reacts with - H2O, H2SO4, HgSO4
→ PRODUCT = Ketone

Question 13

Adding Halogens to Alkynes

Answer 13

→ Starts with - Alkyne
→ Reacts with - 1 or 2 Mol Halogens
→ PRODUCT = Alkene with TRANS Halogens OR Alkane with TRANS Halogens

Question 14

Ozonolysis of Alkynes

Answer 14

→ Starts with - Alkyne

→ Reacts with - 1. O3 2. H2O → PRODUCT = Ozonide

Question 15

Alkylation of Alkynes

Answer 15

→ Starts with - Alkyne
→ Reacts with - Halogen and Base (H2, NaNH2 or LDA)
→ PRODUCT = New Carbon-Carbon Bond with Alkyne

Question 16

Free Radical Halogenation of Alkanes

Answer 16

→ Starts with - Alkane and a Halogen (ex. Cl2)
→ Reacts with - HV, UV or HEAT
→ PRODUCT = Alkane with Halogen attached

Question 17

Free Radical Addition of Hydrogen Halides of Alkenes

Answer 17

→ Starts with - Alkene
→ Reacts with - Hydrogen Halide (alone) OR Hydrogen Halide, UV Light OR Hydrogen Halide, PEROXIDE
→ PRODUCT = Alkane with Halogen attached

Question 18

Metal Ammonia Reduction of Alkynes

Answer 18

→ Starts with - Alkyne
→ Reacts with - Na, NH3
→ PRODUCT = Alkene

Question 19

Free Radical Polymerization of Alkenes

Answer 19

→ Starts with - Alkene
→ Reacts with - PEROXIDE, HEAT
→ PRODUCT = Polymer

Question 20

SN1 Mechanism of Allyl Halides

Answer 20

→ Starts with - Allyl Halide
→ Reacts with - H2O
→ PRODUCT = Allylic Alcohol

Question 21

Allylic Free Radical Halogenation

Answer 21

→ Starts with - Alkene
→ Reacts with - N-Bromosuccinimide, CCl4, HEAT OR N-Chlorosuccinimide, CCl4, HEAT
→ PRODUCT = Alkane with Bromo or Chloro Halogen attached

Question 22

Free Radical Halogenation of Alkenes

Answer 22

→ Starts with - Alkene and Halogen (ex. Cl2)
→ Reacts with - HV, UV or HEAT
→ PRODUCT = Alkane with Halogen attached

Question 23

E1 Mechanism of Dienes

Answer 23

→ Starts with - Alkene and Alcohol
→ Reacts with - Strong Acid (H2SO4), HEAT
→ PRODUCT = Diene

Question 24

E2 Mechanism of Dienes

Answer 24

→ Starts with - Alkene and Alkyl Halide
→ Reacts with - Strong Base (NaOCH2CH3), HEAT
→ PRODUCT = Diene

Question 25

1,2 Addition Mechanism

Answer 25

→ Starts with - Diene
→ Reacts with - Hydrogen Halide (ex. HCl)
→ PRODUCT = Alkene with Halogen attached

Question 26

1,4 Addition Mechanism

Answer 26

→ Starts with - Diene
→ Reacts with - Hydrogen Halide (ex. HCl)
→ PRODUCT = Alkene with Halogen attached