Organic Chemistry- Reactions

Question 1

Hydrohalogenation Alkene

Answer 1

HX, Treatment with an alkene gives a Markov Add of H and X

Question 2

Hydrobromination Alkene

Answer 2

HBr, ROOR

Treatment of alkene gives anti Markov Add of H and Br

Question 3

Acid Catalyzed Hydration Alkene

Answer 3

H3O+

Treatment of alkene gives Markov Add of H and OH. OH at more sub.

Question 4

Oxymerc-demercuration Alkene

Answer 4

1)Hg(OAc)2, H2O
2) NaBH4
Treatment of alkene gives Markov Add of H and OH. No carbocation rearrange

Question 5

Hydroboration Oxidation Alkene

Answer 5

1) BH3 THF
2) H2O2 NaOH
Treatment with alkene gives anti Markov add of H and OH. Syn addition + En

Question 6

Hydrogenation Alkene

Answer 6

H2, Pt

Treatment of alkene gives syn add of H and H

Question 7

Bromination Alkene

Answer 7

Br2

Treatment of alkene gives an anti addition of Br and Br. + En

Question 8

Halohydrin formation Alkene

Answer 8

Br2, H20

Treatment of alkene gives anti add of Br and OH. OH at more subbed. + En

Question 9

Anti Dihydroxylation Alkene

Answer 9

1)RCO3H 2) H3O+

Treatment of alkene converts it to an epoxide, which converts to a trans diol. + En

Question 10

Syn Dihydroxylation #1 Alkene

Answer 10

KMnO4, NaOH, cold

With alkene gives a syn add of OH and OH. +En

Question 11

Syn Dihydroxylation #2 Alkene

Answer 11

1) OsO4 2) NaHSO3, H2O

With alkene gives a syn add of OH and OH. + En

Question 12

Ozonolysis Alkene

Answer 12

1) O3 2) DMS

With alkene cleaves C=C bond, giving two compounds each with C=O bond.

Question 13

Which addition reactions give Markov products? Alkene

Answer 13

Hydrohalogenation, Acid Catalyze Hydration, and Oxymerc-demerc.

Question 14

Which addition reactions give Anti-Markov products? Alkene

Answer 14

Hydrobromination and Hydroboration-oxidation

Question 15

Which addition reactions give Syn addition products? Alkene

Answer 15

Hydrogenation and Syn Didroxylation

Question 16

Which addition reactions give Anti addition products? Alkene

Answer 16

Bromination and Halohydrin formation

Question 17

Which addition reaction gives Trans product? Alkene

Answer 17

Anti dihydroxylation

Question 18

Elimination Alkyne

Answer 18

1) xs NaNH2
2) H20
A vicinal or geminal dibromide alkane is converted to an alkyne

Question 19

Hydrohalogenation Alkyne

Answer 19

HX

Alkyne goes Markov addition x2 forming geminal dihalide.

Question 20

Acid Catalyze Hydration Alkyne

Answer 20

H2SO4, H2O, HgSO4

Terminal alkyne undergoes Markov add of H and OH forming an enol, tautomerizes to ketone.

Question 21

Hydroboration oxidation alkyne

Answer 21

1)R2BH 2) H2O2, NaOH

Terminal alkyne go anti Markov add of H and OH to enol, which tautomerizes to an aldehyde.

Question 22

Halogenation Alkyne

Answer 22

X2, CCl4

Alkyne undergoes add of X and X (xs X2 gives tetrahalide).

Question 23

Ozonolysis Alkyne

Answer 23

1)O3
2)H20
Alkyne is oxidatively cleaves C trip C bond. Internal alkynes are split into two carboxylic acids, while terminal alkynes are converted into a carboxylic acid and carbon dioxide.

Question 24

Hydrogenation alkynes #1

Answer 24

H2, Lindlar’s Catalyst

Internal alkyne goes cis alkene

Question 25

Hydrogenation alkynes #2

Answer 25

H2, Pt

Alkyne goes to alkane

Question 26

Dissolving metal reduction

Answer 26

Na, NH3(l)

Internal alkyne is converted to trans alkene.

Question 27

Alkylation

Answer 27

1) NaNH2
2) RX
Terminal alkyne goes to internal alkyne.

Question 28

Radical bromination

Answer 28

Br2, hv

Alkane undergoes bromination where Br is installed at the most subbed.

Question 29

Radical chlorination

Answer 29

Cl2, hv
Alkane is chlorinated. Less selective than bromination (but faster). Better for situations where one regiochemical outcome is possible.

Question 30

Hydrobromination

Answer 30

HBr, ROOR

Alkene undergoes anti Markov add of H and Br

Question 31

Allylic bromination

Answer 31

NBS, hv

Br installed at allylic position of an alkene