Reaction Pathways Flashcards

1
Q

arene sulfonation

A

c.H2SO4 (reflux)

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2
Q

nitrating arene

A

c.HNO3, c.H2SO4 at <50C

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3
Q

saturating arene

A

H2, Ni catalyst at 300C and 30atm

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4
Q

arene alkylation

A

using haloalkane, AlCl3 catalyst (reflux)

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5
Q

arene acylation

A

acylchloride, AlCl3 catalyst (reflux)

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6
Q

arene chlorination

A

Cl2 (g), AlCl3 (makes Cl2 electrophilic enough to react with arene) catalyst at RT

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7
Q

arene bromination

A

Br2 (l), FeBr3 (makes Br2 electrophilic enough to react with arene) catalyst at RT

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8
Q

why is nitrating arenes done at low temperatures

A

protonated HNO3 very reactive - low temperatures to avoid multiple substitutions

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9
Q

why is a catalyst used to chlorinate/ brominate/ nitrating arenes

A

makes them electrophilic enough to react with benzene

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10
Q

what are the Friedel Crafts Reactions

A

alkylation and acylation

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11
Q

what type of reactions are brominating/ nitrating/ sulfonating arenes

A

(electrophilic) aromatic substitutions

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12
Q

alkene to dihaloalkane

A

Br2 (l)

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13
Q

alkene to alkane

A

H2 (g), Pt catalyst

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14
Q

alkene to alcohol

A

c. H2SO4, H2O (reflux)

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15
Q

alkene to haloalcohol

A

Br2 (aq)

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16
Q

alkene to haloalkane

A

HBr (aq), RT

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17
Q

alkane to haloalkane

A

Cl2, UV light

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18
Q

alcohol to alkene

A

Al2O3, 300C

19
Q

haloalkane to amine

A

c. NH3 (aq), heat in sealed tube

20
Q

haloalkane to alcohol

A

NaOH (reflux)

21
Q

alcohol to haloalkane

A

NaBr, c.H2SO4 (reflux)

22
Q

alcohol to ketone

A

acidified K2Cr2O7 (reflux)

23
Q

alcohol to aldehyde

A

acidified K2Cr2O7 (distil)

24
Q

alcohol to carboxylic acid

A

acidified K2Cr2O7 (reflux)

25
Q

aldehyde/ ketone to alcohol

A

NaBH4, H2O

26
Q

haloalkane to nitrile

A

CN-, ethanol (reflux)

27
Q

nitrile to amine

A

H2, Ni catalyst

28
Q

aldehyde/ ketone to hydroxynitrile

A

acidified NaCN (aq)

29
Q

aldehyde to carboxylic acid

A

acidified K2Cr2O7 (reflux)

30
Q

carboxylic acid to carboxylate

A

NaOH

31
Q

carboxylate to carboxylic acid

A

HCl (aq)

32
Q

carboxylic acid to ester

A

c. H2SO4 catalyst, alcohol

33
Q

ester/ amide to carboxylic acid

A

acid/ alkali (reflux)

34
Q

acid anhydride to ester

A

alcohol, RT

35
Q

acyl chloride to ester

A

alcohol, RT

36
Q

acyl chloride to primary amide

A

NH3, RT

37
Q

acyl chloride to secondary amide

A

NH2, RT

38
Q

ester hydrolysis with H2SO4, H2O

A

carboxylic acid + alcohol

39
Q

amide hydrolysis with H2SO4, H2O

A

carboxylic acid + amine salt

40
Q

ester hydrolysis with NaOH, H2O

A

carboxylate salt + alcohol

41
Q

amide hydrolysis with NaOH, H2O

A

carboxylate salt + amine

42
Q

how is carboxylic acid regained from carboxylate salt produced in basic hydrolysis of ester

A

adding acid (e.g. H2SO4) to re-protonate

43
Q

how is acyl chloride made from carboxylic acid produced in acidic hydrolysis of amide

A

adding SOCl2

44
Q

why is carboxylic acid produced in acidic hydrolysis of amide

A

catalyst is H2SO4 (no Cl2 to produce acyl chloride)