Important functional group interconversions in aromatic systems Flashcards

1
Q

from NH2 –> F

A

i) HNO2 ii) BF4- / /\ (heat)

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2
Q

from NH2 –> Cl

A

i) HNO2 ii) Cu2Cl2

Sandmeyer reaction

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3
Q

from NH2 –> Br

A

i) HNO2 ii) Cu2Br2

Sandmeyer reaction

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4
Q

from NH2 –> I

A

i) HNO2 ii) KI

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5
Q

from CN –> Br

A

i) HNO2 ii) Cu2(CN)2

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6
Q

from NH2 –> SR

A

i) HNO2 ii) NaSR

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7
Q

from NH2 –> OH

A

i) HNO2 ii) H2O / /\ (heat)

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8
Q

from NH2 –> N3

A

i) HNO2 ii) NaN3

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9
Q

from NH2 –> NO2

A
  • i) HNO2 ii) NaNO2
  • CF3CO3H
    oxidation
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10
Q

from NH2 –> H

A

i) HNO2 ii) H3PO2

technically FGA/FGR

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11
Q

from SO3H –> H

A

steam; or H20 / /\ (heat)

technically FGA/FGR

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12
Q

from NO2 –> NH2

A
  • Sn/ HCl; or H2/ Pd
    reduces 2 or more groups
  • Na2S
    reduces 1 of 2 groups
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13
Q

from COCl –> CONR1R2

A

R1R2NH

technically C-N

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14
Q

from COCl –> CO2R

A

ROH

technically C-O

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15
Q

from CO2H –> CO2R

A

ROH / H+ / /\ (heat)

technically C-O

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16
Q

from CO2H –> COCl

A

SOCl2

17
Q

from CH3 –> CO2H

A

KMnO4 (alkaline)

OK for larger alkyl groups

18
Q

from CH=O –> CO2H

A

CrO3; or K2Cr2O7

oxidation

19
Q

from CH2OH –> CH=O

A

MnO2

controlled oxidation

20
Q

from CH=O –> CH2OH

A

NaBH4; LiAlH4

reduction

21
Q

from COR (ketone) –> CHROH

A

NaBH4; or LiAlH4

reduction

22
Q

from NH2 –> NHCOR

A

RCOCl or (RCO)2O

technically C-N

23
Q

from NHCOR –> NH2

A

OH- / H2O / /\ (heat)

hydrolysis

24
Q

from OH –> OCOR

A

RCOCl or (RCO)2O

technically C-O

25
Q

from OCOR –> OH

A

OH- / H2O / /\ (heat)

hydrolysis

26
Q

from COR (ketone) –> CH2R

A

i) HSCH2CH2SH ii) H2 Raney Ni
FGA/FGR

i) Zn / Hg / HCl
acidic FGA/FGR

i) H2NNH2 / KOH / /\ (heat)
basic FGA/FGR