Chapter 10, Organic Synthesis Flashcards

1
Q

Alkene > Haloalkane

A

Electrophilic Addition

HBr

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2
Q

Alkene > Dihaloakane

A

Electrophilic Addition

Br2 in organic solvent

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3
Q

Alkene > Alcohol

A

Electrophilic Addition + Hydrolysis

Conc H2SO4, then H20

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4
Q

Haloalkane > Alcohol

A

Nucleophilc Substitution

NaOH aq solvent, heating under reflux

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5
Q

Haloalkane > Alkene

A

Elimination

NaOH in alcoholic solvent, heating under reflux

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6
Q

Haloalkane > Nitrile

A

Nucleophilic Substitution

NaCN in ethanol, heating under reflux

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7
Q

Haloalkane > Amine

A

Nucleophilic Substitution

NH3 in ethanol, sealed vessel

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8
Q

Alcohol > Ester

A

Esterification

Carboxylic acid, warm, conc H2SO4 (catalyst)

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9
Q

Alcohol > Alkene

A

Elimination

conc H2SO4, heat

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10
Q

Secondary Alcohol > Ketone

A

Oxidation

Acidified Potassium Dichromate

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11
Q

Primary Alcohol > Carboxylic Acid

A

Oxidation

Acidified Potassium Dichromate

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12
Q

Primary Alcohol > Aldehyde

A

Oxidation

Acidified Potassium Dichromate, distillation

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13
Q

Ketone > Secondary Alcohol

A

Reduction

aq NaBH4

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14
Q

Aldehyde or Ketone > Hydroxynitrile

A

Nucleophilc Addition

HCN

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15
Q

Aldehyde > Primary Alcohol

A

Reduction

aq NaBH4

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16
Q

Aldehyde > Carboxylic Acid

A

Oxidation

Acidified Potassium Dichromate, heating under reflux

17
Q

Nitrile > Carboxylic Acid

A
Hydrolysis
dilute acid (HCl), heating under reflux
18
Q

Nitrile > Amine

A

Reduction
H2, Ni catalyst, heat or
LiAlH4, dry ether

19
Q

Ester > Carboxylic Acid and Alcohol

A

Acid hydrolysis

HCl, reflux

20
Q

Ester > Salt of Acid and Alcohol

A

Alkaline hydrolysis

NaOH, reflux

21
Q

Acyl Chloride > Ester

A

Nucleophilic Addition-Elimination

Alcohol (R2OH)

22
Q

Acyl Chloride > Amide

A

Nucleophilic Addition-Elimination

NH3

23
Q

Acyl Chloride > N-Substituted Amide

A

Nucleophilic Addition-Elimination (Acylation)

Amine (R2NH2)

24
Q

Acyl Chloride > Carboxylic Acid

A

Nucleophilc Addition-Elimination (Acylation)

H20

25
Q

Benzene > Nitrobenzene

A
Electrophilic Substitution (Nitration)
conc HNO3, conc H2SO4, reflux
26
Q

Benzene > Phenylethanone

A
Electrophilic Substitution (Friedel-Crafts Acylation)
CH3COCl
27
Q

Nitrobenzene > Phenylamine

A

Reduction

Tin, conc HCl, reflux