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Organic synthesis Flashcards

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1
Q

Rxn of alkanes? Conditions?

A 
FRS to form RX
limited Cl2(g), uv/heat
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2
Q

Rxn of alkenes? Conditions? How many?

A

9
EA: Br2(l) or Br2 in CCl4
EA: Br2(aq)
EA: HBr(g)
EA: conc. H2SO4, H2O(l) heat
Reduction: H2(g) Ni catalyst, high pressure
mild oxidation: cold dil. KMnO4, NaOH(aq)
strong oxidation: KMnO4 dil. H2SO4, heat to give CO2 and H20
strong oxidation: KMnO4 dil. H2SO4, heat to give carboxylic acid, CO2 and H20
strong oxidation: KMnO4 dil. H2SO4, heat to give ketone, CO2 and H2O

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3
Q

Rxn of benzenes? Conditions? How many?

A

3
ES: conc. HNO3, conc. H2SO4 55 degrees
ES: Br2(l) anhydrous FeBr3
ES: CH3Cl, AlCl3 gives methyl benzene

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4
Q

Rxn of methyl benzenes? Conditions? How many?

A 
4
ES: conc. HNO3, conc. H2SO4 30 degrees 
ES: Br2(l) anhydrous FeBr3 
FRS: limited Cl2(g), uv/heat
Oxidation: KMnO4 dil. H2SO4, heat to give benzoic acid
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5
Q

Rxn of halogenoalkanes? Conditions? How many?

A

4
NS: ethanolic NH3, heat in sealed tube gives amine
NS: NaOH(aq) heat gives alcohol
NS: ethanolic KCN heat gives nitrile
Elimination: ethanolic NaOH heat gives alkene

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6
Q

Rxn of primary alcohol? Conditions? How many?

A

9
substitution: PCl5(s) room temp. gives RCL
substitution: Pbr3 gives RBr
substitution: P, I2, heat gives RI
oxidation: K2Cr2O7 dil.H2SO4 heat imm. distill. gives aldehyde
oxidation: KMnO4 dil. H2SO4, heat gives carboxylic acid
oxidation(iodoform): I2(aq), NaOH(aq) warm
condensation: RCO2H, conc. H2SO4 heat or RCOCl room temp. to give ester
redox: Na(s)
elimination: excess conc. H2SO4 heat (170 degrees) gives alkene

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7
Q

Rxn of secondary alcohol? Conditions? How many?

A

8
substitution: PCl5(s) room temp. gives RCL
substitution: Pbr3 gives RBr
substitution: P, I2, heat gives RI
oxidation: KMnO4 dil. H2SO4, heat gives ketone
oxidation(iodoform): I2(aq), NaOH(aq) warm
condensation: RCO2H, conc. H2SO4 heat or RCOCl room temp. to give ester
redox: Na(s)
elimination: excess conc. H2SO4 heat (170 degrees) gives alkene

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8
Q

Rxn of phenol? Conditions? How many?

A 
7
ES: Br2(l) in CCl4 gives mono-sub
ES: Br2(aq) gives tri-sub
ES: dilute HNO3 gives mono-sub
ES: conc. HNO3 gives tri-sub
condensation:RCOCL/RCOBR
redox: Na(s)
acid-base: NaOH(aq)
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9
Q

Rxn of aldehydes? Conditions? How many?

A 
7
Reduction: LiAlH4 in dry ether/ NaBH4/H2, Ni, high temp. and pressure
Oxidation: KMnO4 dil. H2SO4 heat
Oxidation: I2(aq), NaOH(aq) warm
Oxidation: Fehling's solution warm
Oxidation: Tollen's (ammonical silver nitrate) warm
Condensation: 2,4-DNPH
NA: cold HCN with trace KCN
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10
Q

Rxn of ketones? Conditions? How many?

A 
4
Reduction: LiAlH4 in dry ether/ NaBH4/ H2, Ni, high temp. and pressure
Oxidation: I2(aq), NaOH(aq) warm
Condensation: 2,4-DNPH
NA: cold HCN with trace KCN
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11
Q

Rxn of carboxylic acids? Conditions? How many?

A 
5
Reduction; LiAlH4 in dry ether
Substitution: PCl5(s), room temp.
Redox: Na(s)
Acid-base: NaOH(aq)/Na2CO3(aq)/NH3(aq)
Condensation: CH3CH2OH, con. H2SO4, heat
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12
Q

Rxn of acid chlorides? Conditions? How many?

A

6

hydrolysis: H2O(l) gives carboxylic acid
hydrolysis: NaOH(aq)
condensation: CH3CH2OH
condensation: phenoxide ions
condensation: NH3 give amide
condensation: CH3NH2

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13
Q

Rxn of amines? Conditions? How many?

A

3
NS: CH3Br, heat
acid-base: carboxylic acid/ dil. HCl
condensation: CH3COCl gives amino acid

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14
Q

Rxn of amides? Conditions? How many?

A

3
alkaline hydrolysis: NaOH(aq), heat gives salt
acid hydrolysis: dil. H2SO4, heat gives carboxylic acid
reduction: LiAlH4 in dry ether gives amine

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15
Q

Rxn and preparation of phenylamines? Conditions? How many?

A

prepare by reduction of nitrobenzene: 1) Sn, conc. HCl, heat 2) NaOH(aq)
rxn ES: Br2(aq) to give tri-sub

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16
Q

Rxn of nitrile? Conditions? How many?

A

3
acid hydrolysis: dil. H2SO4, heat gives carboxylic acid
alkaline hydrolysis: NaOH(aq), heat gives salt
reduction: LiAlH4 in dry ether/ H2, Ni, high temp. pressure gives amine

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