Test #4 Reactions

Question 1

Hydrohalogenation: Identifier and key features

Answer 1

Has H-X as a reactant, Markovnikov. Rearrangements

Question 2

Hydrohalogenation of alkynes

Answer 2

Has H-X as a reactant. If there’s excess, goes to alkane. Concerted. Markovnikov.

Question 3

Acid-catalyzed hydration/etherification

Answer 3

H2O or RO as a reactant. Markovnikov, rearrangements.

Question 4

Acid-catalyzed hydration/etherification of alkynes

Answer 4

Acid and Water as a reactant. Becomes an Enol then a Ketone. Concerted, Markovnikov.

Question 5

Hydroboration-Oxidation

Answer 5

BH3 is your reactant. Concerted. Syn addition. Anti-Markovnikov.

Question 6

Hydroboration-oxidation of alkynes

Answer 6

BH3 and H202 , OH as reactants. Enol to Ketone. Concerted, Anti Markovnikov. Syn addition.

Question 7

Epoxidation of alkenes

Answer 7

RCO3H or MCPBA as reactants. Makes a tringle on a oxygen. Concerted, Syn addition.

Question 8

Halogenation of alkenes.

Answer 8

X2 as a reactant. Stepwise but no rearrangements. Anti addition. Make a triangle then broken with SN2. No F2

Question 9

Halogenation of alkynes.

Answer 9

X2 as a reactant. Anti addition, can stop after 1 or 2 rounds.

Question 10

Halohydrin formation from alkenes

Answer 10

X2 with H20/ROH. Nucleophile in second step is H2O, ROH. Adds to more substituted carbon.

Question 11

Alpha0halo ketones from alkynes.

Answer 11

X2 and H2O. Enol to Ketone.

Question 12

Anti0dihydroxlation of alkenes

Answer 12

RCO3H is your reactant with Acid. 2 step process. Anti addition, stepwise, make oxygen triangle then acid comes to break it up.

Question 13

Syn- Dihydroxlayion of alkenes

Answer 13

OsO4 +NaHSO3, H2O or Kmno4 and NaOH. Syn addition. Bond to oxygens then make go to OH Groups.

Question 14

Acidic ring opening of epoxides

Answer 14

Starts with an epoxide, acid, and water. Creates a linear figure with OH groups on each end. Anti addition.

Question 15

Basic ring opening of epoxides.

Answer 15

Start with an epoxide and react with a nucleophile, typically a base and H3O+. Makes a linear product with 2 OH groups. Anti addition. Nucleophile goes to less substituted carbon.

Question 16

Ozonolysis

Answer 16

O# and (Ch3)2S as reactants. Cut it in half and tack on O= caps. Alkynes too, with an additional O bond.

Question 17

Hydrogenation of alkenes

Answer 17

Reactants are Pt, PD, Rh, or Ni with H2. Syn addition. Happens with alkynes as well.

Question 18

Partial hydrogenation of alkynes

Answer 18

Reactants are H2 with Pd/CaCO3 (Lindlars catalyst) or Li EtNH2, -78 and H3Cl (Dissolving metal) Syn and anti addition respectively. without touching alkene.

Question 19

Cycloporponation of alkenes with diazomethane

Answer 19

Ch2N2 with heat or light. Makes a triangle with no oxygen. Syn addition. Br or Cl only. Stereochemistry possible.

Question 20

Cycloproponation of alkenes with CHX3.

Answer 20

Reactants are CHX2 and NaOR. Make a triangle with X groups as a hat. Syn addition, Cl or Br only. Steriochemistry.

Question 21

Generation of alkynide nucleophiles.

Answer 21

NH2 and then a chain with BR. Deprotonates the alkyne and attach it to the Br chain via SN2.

Question 22

Free radical halogenation of alkanes

Answer 22

X2 with Light. X is Cl or Br. Br is highly selective. Taking an alkane and adding a X group the hard way.

Question 23

Free radical bromination

Answer 23

NBS with Hv. Adding a br group without taking off the alkene. Major product determined by alkene stability.

Question 24

Radical hydrobromination of alkenes

Answer 24

H-Br and RooR is added to an alkene. Anti Markovnikovs product. Bromination the hard way.

Question 25

Free radical polymerization

Answer 25

Look for polymerization or the addition of just an alkene. Adding on till termination.