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ALIPHATIC COMPOUNDS - REACTION PATHWAYS Flashcards

1
Q

Alkane —> Haloalkane?

A

Halogen
Uv
Free radical substitution

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2
Q

Alkene —> Alkane?

A

H2
Nickel catalyst
Hydrogenation

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3
Q

Alkene —> Haloalkane?

A

Hydrogen halide (g)
Room temp
Electrophilic addition

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4
Q

Alkene —> Alcohol?

A

H2O (steam)
H3PO4, 30O˚C, 60 atm
Electrophilic addition

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5
Q

Haloalkane —> Alcohol?

A

NaOH (aq)
heat under reflux
Nucleophilic substitution

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6
Q

Haloalkane —> Nitrile

A

CN- (eg KCN) / ethanol (as solvent)
heat under reflux
Nucleophilic substitution

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7
Q

Haloalkane —> Amine?

A

NH3 / ethanol (as solvent)
heat
Nucleophilic substitution

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8
Q

Alcohol —> Alkene?

A

-
H3PO4 or conc H2SO4, heat under reflux
Elimination

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9
Q

Alcohol —> Haloalkane?

A

Sodium halide
conc H2SO4, heat under reflux
Nucleophilic substitution

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10
Q

Alcohol —> Ketone?

A

-
K2Cr2O7/H2SO4, reflux
Oxidation

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11
Q

Alcohol —> Aldehyde?

A

-
K2Cr2O7/H2SO4, distillation
Oxidation

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12
Q

Alcohol —> Carboxylic acid?

A

-
K2Cr2O7/H2SO4, reflux
Oxidation

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13
Q

Alcohol —> Ester?

A

carboxylic acid
conc. H2SO4 or acid anhydride
Esterification

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14
Q

Aldehyde —> Alcohol

A

NaBH4
warm
Nucleophilic addition

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15
Q

Aldehyde —> Carboxylic acid?

A

-
K2Cr2O7/H2SO4, reflux
Oxidation

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16
Q

Aldehyde —> Hydroxynitrile?

A

NaCN (aq) / H+(aq)
room temp
Nucleophilic addition

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17
Q

Carboxylic acid —> Acyl chloride?

A

SOCl2
room temp
Nucleophilic addition

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18
Q

Carboxylic acid —> Ester?

A

alcohol
conc H2SO4, heat under reflux
Esterification

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19
Q

Ketone —> Alcohol?

A

Nucleophilic addition

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20
Q

Ketone —> Hydroxynitrile?

A

NaCN (aq) / H+ (aq)
room temp
Nucleophilic addition

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21
Q

Nitrile —> Amine?

A

H2
Nickel catalyst, heat
Hydrogenation / reduction

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22
Q

Nitrile —> Carboxylic acid?

A

H2O/HCl
heat under reflux
Hydrolysis

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23
Q

Hydroxynitrile —> Amine?

A

H2
Nickel catalyst
Hydrogenation / reduction

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24
Q

Ester —> Carboxylic acid?

A

dilute acid
heat under reflux
Hydrolysis

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25
Q

Ester —> Carboxylate?

A

OH-
heat under reflux
Hydrolysis

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26
Q

Acyl chloride —> Carboxylic acid?

A

H2O
room temp
Hydrolysis

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27
Q

Acyl chloride —> Ester?

A

Alcohol
room temp
Nucleophilic substitution

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28
Q

Acyl chloride —> Primary amide

A

NH3
room temp
Nucleophilic substitution

29
Q

Acyl chloride —> Secondary amide?

A

Primary amine
room temp
Nucleophilic substitution

30
Q

Draw the functional group of an alkene

31
Q

Draw the functional group of a Haloalkane

32
Q

Draw the functional group of an Alcohol

A

R - C - OH

33
Q

Draw the functional group of an Aldehyde

A

R - C = O
|
H

34
Q

Draw the functional group of a Carboxylic acid

A

R - C = O
|
OH

35
Q

Draw the functional group of a Ketone

A

R - C = O
|
R’

36
Q

Draw the functional group of a Nitrile

A

_
R - C = N

37
Q

Draw the functional group of a Hydroxynitrile

A

_
R - C - C = N
|
OH

38
Q

Draw the functional group of an Ester

A

R - C = O
|
OR’

39
Q

Draw the functional group of an Acyl chloride

A

R - C = O
|
Cl

40
Q

Draw the functional group of a Carboxylate

A

R - C = O
|
O-

41
Q

Draw the functional group of an Amine

42
Q

Draw the functional group of a primary Amide

A

R - C = O
|
NH2

43
Q

Draw the functional group of a secondary Amide

A

R - C = O
|
NH
|
R’

44
Q

Alkane —>
(include reaction mechanisms)

A

Haloalkane - Free radical substitution

45
Q

Alkene —>

A

Alkane - Hydrogenation
Haloalkane - Electrophilic addition
Alcohol - Electrophilic addition

46
Q

Haloalkane —>

A

Alcohol - Nucleophilic substitution
Nitrile - Nucleophilic substitution
Amine - Nucleophilic substitution

47
Q

Alcohol —>

A

Alkene - Elimination
Haloalkane - Nucleophilic substitution
Ketone - Oxidation
Aldehyde - Oxidation
Carboxylic acid - Oxidation
Ester - Esterification

48
Q

Aldehyde —>

A

Alcohol - Nucleophilic addition
Carboxylic acid - Oxidation
Hydroxynitrile - Nucleophilic addition

49
Q

Carboxylic acid —>

A

Acyl chloride - Nucleophilic substitution
Ester - Esterification

50
Q

Ketone —>

A

Alcohol - Nucleophilic addition
Hydroxynitrile - Nucleophilic addition

51
Q

Nitrile —>

A

Amine - Hydrogenation / Reduction
Carboxylic acid - Hydrolysis

52
Q

Hydroxynitrile —>

A

Amine - Hydrogenation / Reduction
Carboxylic acid - Hydrolysis

53
Q

Ester —>

A

Carboxylic acid - Hydrolysis
Carboxylate - Hydrolysis

54
Q

Acyl chloride —>

A

Carboxylic acid - Hydrolysis
Ester - Nucleophilic substitution
Primary Amide - Nucleophilic substitution
Secondary Amide - Nucleophilic substitution

55
Q

—> Alkane

A

Alkene - Hydrogenation

56
Q

—> Alkene

A

Alcohol - Elimination

57
Q

—> Haloalkane

A

Alkane - Free radical substitution
Alkene - Electrophilic addition
Alcohol - Nucleophilic substitution

58
Q

—> Alcohol

A

Alkene - Electrophilic addition
Haloalkane - Nucleophilic substitution
Aldehyde - Nucleophilic addition
Ketone - Nucleophilic addition

59
Q

—> Aldehyde

A

Alcohol - Oxidation

60
Q

—> Carboxylic acid

A

Alcohol - Oxidation
Aldehyde - Oxidation
Nitrile - Hydrolysis
Hydroxynitrile - Hydrolysis
Ester - Hydrolysis
Acyl chloride - Hydrolysis

61
Q

—> Ketone

A

Alcohol - Oxidation

62
Q

—> Nitrile

A

Haloalkane - Nucleophilic substitution

63
Q

—> Hydroxynitrile

A

Aldehyde - Nucleophilic addition
Ketone - Nucleophilic addition

64
Q

—> Ester

A

Alcohol - Esterification
Carboxylic acid - Esterification
Acyl chloride - Nucleophilic substitution

65
Q

—> Acyl chloride

A

Carboxylic acid - Nucleophilic substitution

66
Q

—> Carboxylate

A

Ester - Hydrolysis

67
Q

—> Amine

A

Haloalkane - Nucleophilic substitution
Nitrile - Hydrogenation / Reduction
Hydroxynitrile - Hydrogenation / Reduction

68
Q

—> Primary Amide / Secondary Amide

A

Acyl chloride - Nucleophilic substitution

Chemistry (33 decks)

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