CH2601 FGI Reactions

Question 1

Adding water across a double bond

Answer 1

Use:

• hydroboration oxidation (H adds to side that can stabilise positive charge)
• oxymercuration (OH adds to side that can stabilise positive charge)

Question 2

Oxymercuration

Answer 2

Adds H2O across a bond - OH adds where positive charge can be stabilised).
Uses Hg(OAc)2 and NaBH4.

Question 3

Hydroboration Oxidation

Answer 3

Adds H2O across a bond - H adds where positive charge can be stabilised.
Uses BH3.THF and H2O2/NaOH.

Question 4

Dihydroxylation

Answer 4

Adds two OH groups across a double bond.

Uses OsO4.

Question 5

Ozonolysis

Answer 5

Breaks a C=C bond to form two ketones/aldehydes.

Uses O3 and Me2S.

Question 6

Epoxidation

Answer 6

Forms epoxide ring between between a peroxycarboxylic acid and an alkene.
All bond breaking/forming steps happen simultaneously.

Question 7

Epoxide Ring Opening

Answer 7

Opens an epoxide ring to form two alcohols on one compound.
Uses amine nucleophile/organolithium.
Can also do by hydrolysis (using water)

Question 8

Reduction of epoxides

Answer 8

Epoxide ring to alcohol.

Uses AlH3.

Question 9

Hydrogendation of alkynes

Answer 9

Alkyne to alkene.

Uses NaNH2 and NH3 or Lindlar’s catalyst (poisoned palladium catalyst) with H2.

Question 10

Wolf Kishner Reduction

Answer 10

Ketone/aldehyde to alkane. 
Uses hydrazine (NH2NH2), a base and thermal conditions.

Question 11

Swern Oxidation

Answer 11

Primary alcohol to an aldehyde. 
Uses DMSO (Me2SO), (COCl)2 and a base.

Question 12

Baeyer-Villager Reaction

Answer 12

Ketone to ester.

Uses mCPBA.

Question 13

DCC Coupling

Answer 13

Acid to amide.

Uses DCC.

Question 14

Amide reduction

Answer 14

Reduced an amide.

Uses LiAlH4

Question 15

Mitsunobu Reaction

Answer 15

Replaces OH group with a nucleophile.

Uses PPh3, DEAD, and the nucleophile (which should be acidic to protonate DEAD).

Question 16

Garbiel Synthesis

Answer 16

Primary alkyl halide to primary amine.

Uses phthalimide.