Synthesis Flashcards by A Gonzalez | Brainscape

Q

ALKANE (3)

A

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

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Q

ALDEHYDE (4)

A

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

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Q

ALKENE (4)

A

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

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Q

ACETYLIDE (1)

A

• alkyne (NaNH2, NH3)

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Q

ALKOXIDE (1)

A

• alcohol (NaH)

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Q

EPOXIDE (2)

A

vicinal halhydrin (NaOH)

* alkene (mCPBA)

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Q

CYCLIC PROPANES (2)

A

alkene (CH2I2, Zn/Cu)

* alkene (CHCl3, KOtBu)

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Q

CARBOXLYIC ACID (2)

A

1˚ alcohol (CrO3, H2O)

* alkene (1. O3, 2. H2O2)

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Q

ALLYL BROMIDE (2)

A

alkene (NBS, CCl4)

* alkene (Br2, hv)

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Q

ALKYL HALIDES (many)

A

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)

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Q

DISULFIDE (1)

A

• thiol (NaOH, I2)

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Q

GEMINAL DIHALIDE (1)

A

• alkyne (H-X, 2 eq.)

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Q

KETONE (5)

A

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

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Q

VICINAL DIOL (2)

A

alkene (OsO4, H2O)

* epoxide (H2O, H+)

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Q

VICINAL HALOETHER (1)

A

• alkene (R-OH, X2)

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Q

VICINAL HALOHYDRIN (1)

A

• alkene (X2, H2O)

Q

VICINAL HYDROXYETHER (2)

A

epoxide (NaOCH3, CH3OH)

* epoxide (CH3OH, H+)

Q

VICINAL DIHALIDE (1)

A

• alkene (X2)

Q

VINYL HALIDE (1)

A

• alkyne (H-X, 1 eq.)

Q

NITRILE (1)

A

• 1˚ or 2˚ alkyl halide (CN-)

Q

SULFONIC ACID (1)

A

• thiol (HNO3)

Q

THIOLATE (1)

A

• thiol (NaOH)

Q

THIOETHER (1)

A

• thiolate (R-X)

Q

ETHER (4)

A

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˚

Q

ALCOHOL (many)

A

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)