Synthesis

Question 0

ALKANE (3)

Answer 0

• alkene (H2, Pd/C)
• alkyne (H2, Pd/C)
• alkyl halide (1. Mg, Et2O, 2. H2O)

Question 1

ALDEHYDE (4)

Answer 1

• 1˚ alcohol (CrO3, pyr)
• alkene (1. O3, 2. Me2S)
• alkyne (1. R2BH, 2. H2O2, NaOH)
• vicinal diol (HIO4)

Question 2

ALKENE (4)

Answer 2

• 1˚or 2˚ alkyl halide (R–O- via E2)
• 2˚ or 3˚ OH (H2SO4 via E1)
• alkyne (H2, Lindlar)
• alkyne (Na, NH3)

Question 3

ACETYLIDE (1)

Answer 3

• alkyne (NaNH2, NH3)

Question 4

ALKOXIDE (1)

Answer 4

• alcohol (NaH)

Question 5

EPOXIDE (2)

Answer 5

• vicinal halhydrin (NaOH)

* alkene (mCPBA)

Question 6

CYCLIC PROPANES (2)

Answer 6

• alkene (CH2I2, Zn/Cu)

* alkene (CHCl3, KOtBu)

Question 7

CARBOXLYIC ACID (2)

Answer 7

• 1˚ alcohol (CrO3, H2O)

* alkene (1. O3, 2. H2O2)

Question 8

ALLYL BROMIDE (2)

Answer 8

• alkene (NBS, CCl4)

* alkene (Br2, hv)

Question 9

ALKYL HALIDES (many)

Answer 9

• 1˚ or 2˚ alcohol (PBr3)
• 1˚ or 2˚ alcohol (SOCl2, pyr)
• 1˚ or 2˚ alkyl halide (Br- or I-)
• 1˚ alcohol (HBr or HI via SN2)
• 3˚ alcohol (HBr, HI, or HCl via SN1)
• alkene (H-X)
• alkene (H-X, ROOR)

Question 10

DISULFIDE (1)

Answer 10

• thiol (NaOH, I2)

Question 11

GEMINAL DIHALIDE (1)

Answer 11

• alkyne (H-X, 2 eq.)

Question 12

KETONE (5)

Answer 12

• 2˚ alcohol (CrO3)
• alkene (1. O3, 2. Me2S)
• alkene (1. O3, 2. H2O2)
• alkyne (Hg+2, H2O, H+)
• vicinal diol (HIO4)

Question 13

VICINAL DIOL (2)

Answer 13

• alkene (OsO4, H2O)

* epoxide (H2O, H+)

Question 14

VICINAL HALOETHER (1)

Answer 14

• alkene (R-OH, X2)

Question 15

VICINAL HALOHYDRIN (1)

Answer 15

• alkene (X2, H2O)

Question 16

VICINAL HYDROXYETHER (2)

Answer 16

• epoxide (NaOCH3, CH3OH)

* epoxide (CH3OH, H+)

Question 17

VICINAL DIHALIDE (1)

Answer 17

• alkene (X2)

Question 18

VINYL HALIDE (1)

Answer 18

• alkyne (H-X, 1 eq.)

Question 19

NITRILE (1)

Answer 19

• 1˚ or 2˚ alkyl halide (CN-)

Question 20

SULFONIC ACID (1)

Answer 20

• thiol (HNO3)

Question 21

THIOLATE (1)

Answer 21

• thiol (NaOH)

Question 22

THIOETHER (1)

Answer 22

• thiolate (R-X)

Question 23

ETHER (4)

Answer 23

• 1˚ alkyl halide (R–O- via SN2) - 1˚/1˚ or 1˚/2˚
• 2˚ alkyl halide (R–OH via SN1) - 1˚/2˚
• alkene (1. Hg(OAC2), R–OH, 2. NaBH4) 2˚/2˚
• alkene (R-OH, H+) - 3˚

Question 45

ALCOHOL (many)

Answer 45

* 1˚ alkyl halide (NaOH) * 2˚ or 3˚ alkyl halide (H2O) * aldehyde or ketone (NaBH4, EtOH) * alkene (1. BH3, THF, 2. H2O2, NaOH) * alkene (H2O, H+) * alkene (1. Hg(OAc)2, H2O, 2. NaBH4) * epoxide (1. R-MgBr, 2. H+ workup)