Old Reactions

Question 1

Addition of HX to alkene/alkyne

Answer 1

Alkene: Halogen goes to most sub, carbocation, enantiomers
Alkyne: Halogen goes to most sub, anti with H, 2X=same carbon

Question 2

Addition of HBr and peroxides to alkene/alkyne

Answer 2

Anti-markovnikov, least sub, 2X=same carbon

Question 3

Addition of H+/H2O to alkene

Answer 3

Alkene to alcohol, OH on most sub, carbocation, enantiomers

Question 4

Addition of X2 in CCl4 or H2O

Answer 4

With CCl4 forms alkane dihalide

With H2O forms halohydrins (OH on most sub)

Question 5

Addition of KMnO4/OH- to alkenes (cold and dulute or hot and with acid)

Answer 5

Cold/Dilute/OH- turns alkenes into cis-1,2-diols

Hot/OH- and H+ turns alkenes into carboxylic acids, ketones, or CO2/H2O (1, 0, or 2 hydrogens)

Question 6

Addition of EtONa to halides

Answer 6

Williamson Ether Synthesis (Methyl and 1* halides)

Question 7

Hydrogenation of alkynes

Answer 7

Alkyne + H2 with NiB2(P-2) or Pd/CaCO3 → Cis-alkenes

Alkyne + Li/NH3 or Na/NH3 → Trans-alkanes

Question 8

Give a basic description of a Sn1 reaction

Answer 8

substitution with carbocation intermediate, weak nucleophile, polar protic solvent

Question 9

Give a basic description of a Sn2 reaction

Answer 9

direct substitution with inverstion, small/strong nucleophile, polar aprotic solvent

Question 10

Give a basic description of an E1 reaction

Answer 10

elimination with carbocation intermediate to produce =, strong acid, polar protic solvent

Question 11

Give a basic description of an E2 reaction

Answer 11

direct elimination with = on more substituted (unless very bulky), strong base, polar aprotic