Mechanisms

Question 1

Hydrohalogenation

Answer 1

HX across double bond, halo at mark

Question 2

Hydrohalo with HOOH

Answer 2

Halo at less sub

Question 3

Acid catalyzed hydration

Answer 3

H2O across double bond in presence of an acid- OH at mark

Question 4

Oxy demurc

Answer 4

OH at mark, HgOAC at anti mark which is removed. Requires NABH4 to take Hg off, replacing it with H

Question 5

Hydroboration oxidation

Answer 5

Uses BG3/THF, then H2O2 and NAOH. OH at anti mark, H at mark

Question 6

Catalytic hydration

Answer 6

Syn addition of H2 across db- Uses H2 and PT.

Question 7

Halo and halohydrin

Answer 7

Halogen added (anti and enantiomers) across DB

Question 8

If halohydrins are done in nucleophilic solvents

Answer 8

Nucleophiles may be added

Question 9

Anti-dihydroxylation

Answer 9

OH added at both ends of ethylene =

Question 10

Epoxide

Answer 10

Done with peracid (acid with acidic -ooh group)- used to make epoxides

Question 11

Syn dihydroxylation

Answer 11

OsO4/Ox agent (or KMnO4 and NaOH, cold, dilute) creates syn addn of OH

Question 12

Oxidative cleavage

Answer 12

Cutting db in hald (with o3 and DMS for ozonolysis or KMnO4 and concentration heat for permaganatecleavage)

Question 13

________ eliminates halo from anti mark, ________ adds it to mark

Answer 13

NaOMe, HBr

Question 14

Halogen and water

Answer 14

Anti and enantiomer- OH at mark, halo at anti mark

Question 15

mCPBA and H3O+

Answer 15

Anti and enantiomer addition of OH across DB

Question 16

D2 and Pd

Answer 16

Syn addition of O across DB and enantiomer

Question 17

H+ and H2O

Answer 17

OH at mark

Question 18

EtOH at oxy demurc

Answer 18

OEt substitutes

Question 19

Elimination for alkynes

Answer 19

Strong base just leaves r groups- (-) charged base attacks H, electrons move to other H and then halogen, taking it off. Repeat.

Question 20

NaNH2 and NH3, then H2O

Answer 20

Take off H and halogen (may add more bonds)

Question 21

H2 and Pt or Pd

Answer 21

Catalytic hydration- Gets rid of extra bonds

Question 22

How to stop H2 from taking off all bonds?

Answer 22

Poisoned (Lindlar’s catalyst)

Question 23

Na and NH3

Answer 23

Takes 1 bond off