Synthesis strategies

Question 1

Alkyne

Answer 1

C triple bonded to C

Question 2

Alkene

Answer 2

C double bonded to C

Question 3

Alkane

Answer 3

C single bonded to C

Question 4

Ketones/aldehydes

Answer 4

C double bonded to O

Question 5

Ketone

Answer 5

Not terminal

Question 6

Aldehyde

Answer 6

Terminal

Question 7

Alcohol

Answer 7

C bonded to OH

Question 8

Alkyl Halide

Answer 8

C bonded to Br

Question 9

H2, Lindlar’s catalyst or Na, NH3

Answer 9

Alkyne to Alkene

Question 10

1. Br2
2. XS NaNH2
3. H2O

Answer 10

Alkene to Alkyne

Question 11

H2, Pt/Pd/Ni

Answer 11

Alkene to alkane

Question 12

Br2, hv

Answer 12

Alkane to Alkyl Halide

Question 13

NaOH (SN2) or H2O (SN1)

Answer 13

Alkyl halide to alcohol

Question 14

HX OR SOCl2/py OR PBr3
OR 1. TsCl/py
2. NaX

Answer 14

Alcohol to Alkyl Halide

Question 15

NaOMe or t-BUOK

Answer 15

Alkyl Halide to Alkene

Question 16

HX or HBr, ROOR

Answer 16

Alkene to Alkyl halide

Question 17

H2SO4, H2O, HgSO4 or
1. R2BH
2. H2O2, NaOH

Answer 17

Alkyne to Ketone/Aldehyde

Question 18

Conc. H2SO4, heat OR
1. TsCl/pyr
2. NaOMe

Answer 18

Alcohol to alkene

Question 19

H3O+ OR
1. BH3, THF
2. H2O2, NaOH
OR
1. Hg(OAc)2, H2O
2. NaBH4, NaOH

Answer 19

Alkene to alcohol

Question 20

1. LiAlH4
2. H3O+
   OR
3. NaBH4, MeOH

Answer 20

Ketone/aldehyde to alcohol

Question 21

Alcohol to Ketone/aldehyde

Answer 21

H2CrO4 OR PCC OR DMP OR Swern