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CA1 - Org chem functional grps > Functional grps > Flashcards

Functional grps Flashcards

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1
Q

Free radical substitution (SR)

A

General reaction mechanism of alkanes

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2
Q

Electrophilic addition (AE)

A

General reaction mechanism of alkenes and alkynes

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3
Q

Electrophilic substitution (SE)

A

General reaction mechanism of aromatics

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4
Q

Nucleophilic substitution (SN)

A

General reaction mechanism of alkyl halides and alcohols

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5
Q

Nucleophilic addition (AN)

A

General reaction mechanism of Carbonyl compounds (aldehydes and ketones)

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6
Q

Nucleophilic acyl substitution (SNAcyl)

A

General reaction mechanism of carboxylic acids and their derivatives

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7
Q

Redox

A

General reaction mechanism of alcohols, carbonyl compounds, and carboxylic acids

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8
Q

Reactions undergone:
1. Complete Combustion
2. Incomplete Combustion
3. Free radical Substitution (SR)

A

Alkane

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9
Q
  • Sufficient oxygen is present
  • Reagent: sufficient O2
  • Catalyst: heat
  • Products: CO2 and H2O

(alkane)

A

Complete combustion

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10
Q
  • Insufficient oxygen is present
  • Reagent: limited O2
  • Catalyst: heat
  • Products: CO and H2O

(alkane)

A

Incomplete combustion (alkane)

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11
Q
  • Small reacting molecule replaces an atom or a group of atoms on a hydrocarbon or hydrocarbon derivative
  • It is also known as ALKANE HALOGENATION because the “free radical” is derived from a halogen molecule.
A

Free-radical substitution

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12
Q
  • Reagent: X2
    o Catalyst: Presence of UV light
    o Product: alkyl halide
A

Free-radical substitution

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13
Q

Reactions undergone:
1.Combustion
a. Complete Combustion
b. Incomplete Combustion

  1. Electrophilic Addition (AE)
    a. Symmetrical

b. Asymmetrical

A

Alkene

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14
Q

Symmetrical electrophilic addition

A

i. Hydrogenation
ii. Halogenation

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15
Q

Asymmetrical electrophilic addition

A

i. Hydrohalogenation
ii. Hydration

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16
Q
  • It is also known as reductive/catalytic hydrogenation.
    *Hydrogen atom is added to each carbon atom of a double bond
A

HYDROGENATION

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17
Q
  • Reagent: H2
  • Catalyst: Pt, Pd, Ni
  • Product: double bond becomes a single bond
A

Hydrogenation

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18
Q

Halogen atom is added to each carbon atom of a double bond

A

Halogenation

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19
Q
  • Reagent: X2
  • Catalyst: DCM (dichloromethane)
  • Product: Alkyl dihalide (or vicinal dihalide)
A

Halogenation

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20
Q
  • Hydrogen halide (HCl, HBr, or HI) is incorporated into molecules of an organic compound
    o follows Markovnikov’s Rule
A

HYDROHALOGENATION

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21
Q
  • Reagent: HX
  • Catalyst: ether
  • Product: Alkyl halide
A

Hydrohalogenation

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22
Q
  • aka acid-catalyzed hydration
  • H2O is incorporated into molecules of an organic compound
    o follows Markovnikov’s Rule
A

Hydration

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23
Q
  • Reagent: H2O
  • Catalyst: H2SO4 or H+
    o sometimes the reagent and catalyst are combined together and written as H3O+
  • Product: Alcohol
A

Hydration

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24
Q

This rule is applied to asymmetrical addition reactions of alkenes and alkynes (i.e., in hydrohalogenation and hydration reactions)

A

THE MARKOVNIKOV’S RULE

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25
Q

states that when an asymmetrical molecule of the form HQ adds to an asymmetrical alkene, the hydrogen atom from the HQ becomes attached to the unsaturated carbon atom that already has the most hydrogen atoms.

A

THE MARKOVNIKOV’S RULE

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26
Q

Reactions undergone:
1. Combustion
2. Electrophilic Addition (AE)

A

Alkyne

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27
Q

i. Partial Hydrogenation
ii. Complete Hydrogenation
iii. Partial Halogenation
iv. Complete Halogenation

A

Symmetrical electrophilic addition

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28
Q

i. Partial Hydrohalogenation
ii. Complete Hydrohalogenation
iii. Hydration

A

Asymmetrical electrophilic addition

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29
Q
  • Hydrogen atom is added to each carbon atom of a triple bond
  • Reagent: 1 mole of H2
  • Catalyst: Lindlar’s Catalyst
  • Product: triple bond becomes a double bond
A

Partial hydrogenation

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30
Q

is a heterogeneous catalyst consisting of palladium (Pd) deposited on calcium carbonate or barium sulfate.

A

Lindlar’s Catalyst

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31
Q
  • 2 molecules of Hydrogen are added to each carbon atom of a triple bond
A

complete hydrogenation

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32
Q
  • Reagent: 2 moles of H2
  • Catalyst: Pt/Pd/Ni
  • Product: triple bond becomes a single bond
A

Complete hydrogenation

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33
Q
  • Halogen atom is added to each carbon atom of a triple bond
  • Reagent: 1 mole of X2
  • Catalyst: DCM
  • Product: alkene dihalide (vicinal dihalide)
A

Partial Halogenation

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34
Q
  • Halogen atom is added to each carbon atom of a triple bond
  • Reagent: 2 moles of X2
  • Catalyst: DCM
  • Product: alkyl tetrahalide
A

Complete halogenation

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35
Q
  • 1 molecule of hydrogen halide (HCl, HBr, or HI) is incorporated into molecules of an organic compound
    o follows Markovnikov’s Rule
A

Partial hydroghalogenation

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36
Q
  • Reagent: 1 mole of HX
  • Catalyst: ether
  • Product: Alkene halide (vinyl halide)
A

PARTIAL HYDROHALOGENATION

37
Q
  • 2 molecules of hydrogen halide (HCl, HBr, or HI) is incorporated into molecules of an organic compound
    o follows Markovnikov’s Rule
  • Reagent: 2 moles of HX
  • Catalyst: ether
  • Product: Alkyl dihalide (or geminal dihalide)
A

Complete hydrohalogenation

38
Q
  • aka acid-catalyzed hydration
  • H2O is incorporated into molecules of an organic compound
    o follows Markovnikov’s Rule
  • Reagent: H2O
  • Catalyst: H2SO4 , HgSO4
  • Product: enol (which can undergo keto-enol tautomerism)
A

Hydration (alkyne)

39
Q

Reactions undergone:
1.Electrophilic Substitution (SE)

A

Arene (aromatics)

40
Q

Under Electrophilic Substitution (SE)

A

a. Halogenation
b. Sulfonation
c. Nitration
d. Complete reduction of Benzene
e. Friedel-Crafts Alkylation
f. Friedel-Crafts Acylation

41
Q
  • A hydrogen atom on a benzene ring can be replaced by bromine or chlorine if benzene is treated with a halogen (usually Br2 or Cl2) in the presence of a catalyst
A

Halogenation (arene)

42
Q
  • Reactant: Br2 or Cl2
  • Catalyst: FeBr3, FeCl3 , AlBr3, AlCl3
  • Product: halobenzene
A

Halogenation (arene)

43
Q
  • A hydrogen atom on a benzene ring can be replaced by sulfonic acid if benzene is treated with SO3 in the presence of fuming sulfuric acid
A

SULFONATION

44
Q
  • Reactant: concentrated H2SO4 or SO3
  • Catalyst: fuming H2SO4
  • Product: benzenesulfonic acid
A

Sulfonation

45
Q
  • A hydrogen atom on a benzene ring can be replaced by a nitro group if benzene is treated with HNO3 in the presence of sulfuric acid.
A

Nitration

46
Q
  • Reactant: conc. HNO3
  • Catalyst: conc. H2SO4
  • Product: nitrobenzene
A

Nitration

47
Q
  • 3 H2 molecules are added into the benzene ring to completely remove all the double bonds.
A

Complete reduction of benzene

48
Q
  • Reactant: 3 H2
  • Catalyst: Pt/Pd/Ni + heat
  • Product: cyclohexane
A

Complete reduction of benzene

49
Q
  • An alkyl group (R–) from an alkyl chloride (R–Cl) substitutes for a hydrogen atom on the benzene ring.
  • Alkylation is the most important industrial reaction of benzene.
A

FRIEDEL-CRAFTS ALKYLATION

50
Q
  • Reactant: alkyl halide
  • Catalyst: AlCl3
  • Product: alkylbenzene
A

FRIEDEL-CRAFTS ALKYLATION

51
Q
  • An acyl group (RC=O–) from an acyl chloride (RC=OCl) substitutes for a hydrogen atom on the benzene ring.
A

FRIEDEL-CRAFTS ACYLATION

52
Q
  • Reactant: acyl halide
  • Catalyst: AlCl3
  • Product: acylbenzene
A

FRIEDEL-CRAFTS ACYLATION

53
Q

Reactions undergone:
1. Nucleophilic substitution (SN)
2. Oxidation
3. Dehydration

A

Alcohol

54
Q

Alcohol halogenation with:

A

i. with PBr3
ii. with SOCl2

55
Q
  • A bromine atom is substituted for the hydroxyl group
  • Reagent: PBr3
  • Catalyst: Ether
  • Product: Alkyl bromide
A

HALOGENATION WITH PHOSPHORUS TRIBROMIDE

56
Q
  • A chlorine atom is substituted for the hydroxyl group
  • Reagent: SOCl2
  • Catalyst: pyridine
  • Product: Alkyl chloride
A

HALOGENATION WITH THIONYL CHLORIDE

57
Q
  • Reagent: Mild oxidizing agent
  • Catalyst: N/A
  • Product: aldehyde
A

PARTIAL OXIDATION OF PRIMARY ALCOHOL

58
Q
  • Reagent: Strong oxidizing agent
  • Catalyst: N/A
  • Product: carboxylic acid
A

FULL OXIDATION OF PRIMARY ALCOHOL

59
Q
  • Reagent: Either a mild or strong oxidizing agent
  • Catalyst: N/A
  • Product: ketone
A

OXIDATION OF SECONDARY ALCOHOL

60
Q
  • Reaction in which water is formed from the removal of the components of water (H and OH) from a single reactant
  • This is an example of an ELIMINATION reaction.
    o follows Zaitsev’s Rule
A

DEHYDRATION

61
Q
  • Reagent: Sulfuric acid (H2SO4)
  • Catalyst: Heat; likely at higher temperatures (~180°C)
  • Product: alkene
A

DEHYDRATION

62
Q

Mild/weak oxidizing agents

A

o PCC (pyridinium chlorochromate)
o PDC (pyridinium dichromate)
o Periodinane
o Swern
o DMP (Dess-Martin)

63
Q

Strong OA

A

o KMnO4 (potassium permanganate)
o K2Cr2O7 (potassium dichromate)
o H2CrO4 (chromic acid)

64
Q

Mild/weak RA

A

NaBH4

65
Q

Strong RA

A

LiAlH4

66
Q
  • a rule that carries the name of the Russian chemist
  • major product is the alkene that has the greatest number of alkyl groups attached to the carbon atoms of the double bond.
A

Zaitsev’s rule

67
Q

Reactions undergone:
1. NUCLEOPHILIC ADDITION (AN)
2. NUCLEOPHILIC ADDITION + ELIMINATION (ANE)
3. REDOX

A

Aldehyde or Ketone

68
Q

Under NUCLEOPHILIC ADDITION (AN) (Aldehyde or Ketone)

A

a. Hydration
b. Addition of 1 mole of alcohol

69
Q

Under NUCLEOPHILIC ADDITION + ELIMINATION (ANE) (Aldehyde or Ketone)

A

a. Addition of two moles of alcohol
b. Addition of ammonia/primary amine
c. Grignard reaction (RMgX)

70
Q
  • Reagent: H2O
  • Catalyst: H2SO4, H3O+, or OH-
  • Product: Gem diol (hydrate)
A

Hydration

71
Q
  • Reagent: 1 mole of alcohol (ROH)
  • Catalyst: H2SO4, H3O+, or H+
  • Product: hemiacetal or hemiketal
A

ADDITIONAL OF 1 MOLE OF ALCOHOL

72
Q
  • Reagent: 2 moles of alcohol (ROH)
    o or just add another 1 mole of alcohol to the hemiacetal formed
  • Catalyst: H2SO4, H3O+, or H+
  • Product: acetal or ketal
A

ADDITION OF 2 MOLES OF ALCOHOL

73
Q
  • The reaction of aldehydes and ketones with ammonia or 1º-amines forms imine derivatives, also known as Schiff bases (compounds having a C=N function).
A

ADDITION OF AMMONIA/PRIMARY AMINE

74
Q
  • Reagent: NH3 or RNH (primary amine)
  • Catalyst: H2SO4, H3O+, or H+
  • Product: Imine (or Schiff base)
A

ADDITION OF AMMONIA/PRIMARY AMINE

75
Q
  • Reagent: Grignard Reagent (RMgX)
    o R = an alkyl group
    o Mg = magnesium
    o X = a halogen
  • Catalyst: Ether and Hydrogen ion/Hydronium ion (H3O+)
  • Product: Secondary alcohol (aldehyde); tertiary alcohol (ketone)
A

GRIGNARD REACTION (using RMgX reagent)

76
Q
  • Reagent: Either a mild or strong reducing agent
  • Catalyst: N/A
  • Product: primary alcohol
A

REDUCTION OF ALDEHYDE

77
Q
  • Reagent: Either a mild or strong reducing agent
  • Catalyst: N/A
  • Product: secondary alcohol
A

REDUCTION OF KETONE

78
Q
  • Reagent: Either a mild or strong oxidizing agent
  • Catalyst: N/A
  • Product: carboxylic acid
A

OXIDATION OF ALDEHYDE

79
Q

Reactions undergone:
1. NUCLEOPHILIC SUBSTITUTION (SNAcyl)
2. REDOX
a. Partial reduction
b. Full reduction

A

Carboxylic acid

80
Q

Under NUCLEOPHILIC SUBSTITUTION (SNAcyl)

A

a. Fischer Esterification
b. Ammonolysis
c. Aminolysis
d. Acyl halide formation
e. Hydrolysis of any carboxylic acid derivative

81
Q
  • An esterification reaction is the condensation reaction of a carboxylic acid with an alcohol (or a phenol) to produce an ester.
A

FISCHER ESTERIFICATION

82
Q
  • Reagent: Alcohol
  • Catalyst: H2SO4, H+, or H3O+
  • Product: Ester
A

FISCHER ESTERIFICATION

83
Q
  • Reagent: Ammonia (NH3)
  • Catalyst: Heat
  • Product: Amide
A

AMMONOLYSIS

84
Q
  • Reagent: primary or secondary amine
  • Catalyst: Heat
  • Product: Amide
A

AMINOLYSIS

85
Q
  • Reagent: SOCl2 (thionyl chloride)
  • Catalyst: Use an acid catalyst if reactant is ester; DCC if reactant is an amide
  • Product: Acyl chloride
A

ACYL HALIDE FORMATION

86
Q
  • Reagent: H2O
  • Catalyst: H2SO4 or H+
    o sometimes the reagent and catalyst are combined together and written as H3O+
  • Product: Carboxylic acid
A

HYDROLYSIS OF ANY CARBOXYLIC ACID DERIVATIVE

87
Q
  • Reagent: weak reducing agent
  • Catalyst: N/A
  • Product: aldehyde
A

PARTIAL REDUCTION OF CARBOXYLIC ACID AND DERIVATIVES

88
Q
  • Reagent: strong reducing agent
  • Catalyst: N/A
  • Product: primary alcohol
A

FULL REDUCTION OF CARBOXYLIC ACID AND DERIVATIVES

CA1 - Org chem functional grps (2 decks)

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