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chemistry > CD j: Organic synthesis > Flashcards

CD j: Organic synthesis Flashcards

1
Q
A
  1. Electrophilic substitution
  2. Reduction
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2
Q
  • Give the reactant(s) required for the conversion of an alkene to an alcohol.
  • What is the name of this reaction?
  • What mechanism occurs?
  • State the conditions required.
A
  • Alkene + water
  • Hydration
  • Electrophilic addition
  • H3PO4, steam, heat, pressure or conc. H2SO4, then water

Topic: DF

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3
Q
  • Give the reactant(s) required for the conversion of an alcohol to an alkene.
  • What is the name of this reaction?
  • State the conditions required.
A
  • Alcohol
  • Dehydration, elimination
  • Conc. H2SO4, reflux or Al2O3, heat

​Topic: WM

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4
Q
  • Give the reactant(s) required for the conversion of an alkene to an alkane.
  • What is the name of this reaction?
  • What mechanism occurs?
  • State the conditions required.
A
  • Alkene + hydrogen
  • Hydrogenation
  • Electrophilic addition
  • Ni, heat, pressure or Pt, RTP

Topic: DF

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5
Q
  • Give the reactant(s) required for the conversion of a haloalkane to an alcohol.
  • What mechanism occurs?
  • State the conditions required.
A
  • Haloalkane, ethanolic NaOH or haloalkane, H2O
  • Nucleophilic substitution
  • Reflux

Topic: OZ

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6
Q
  • Give the reactant(s) required for the conversion of an alcohol to a haloalkane.
  • What mechanism occurs?
  • State the conditions required.
A
  • Alcohol, halide ion
  • Nucleophilic substitution
  • H2SO4 or HCl

​Topic: OZ

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7
Q
  • Give the reactant(s) required for the conversion of a haloalkane to an amine.
  • What mechanism occurs?
  • State the conditions required.
A
  • Haloalkane, conc. NH3(aq)
  • Nucleophilic substitution
  • Heat in sealed tube

Topic: OZ

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8
Q
  • Give the reactant(s) required for the conversion of a primary alcohol to an aldehyde.
  • What is the name of this reaction?
  • State the conditions required.
A
  • Primary alcohol, Cr2O72-/H+(aq)
  • Oxidation, condensation
  • Distil

Topics: WM, CD

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9
Q
  • Give the reactant(s) required for the conversion of an aldehyde to a carboxylic acid.
  • What is the name of this reaction?
  • State the conditions required.
A
  • Aldehyde, Cr2O72-/H+(aq)
  • Oxidation, condensation
  • Reflux

Topics: WM, CD

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10
Q
  • Give the reactant(s) required for the conversion of a primary alcohol to a carboxylic acid.
  • What is the name of this reaction?
  • State the conditions required.
A
  • Primary alcohol, Cr2O72-/H+(aq)
  • Oxidation, condensation
  • Reflux

Topics: WM, CD

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11
Q
  • Give the reactant(s) required for the conversion of a secondary alcohol to a ketone.
  • What is the name of this reaction?
  • State the conditions required.
A
  • Secondary alcohol, Cr2O72-/H+(aq)
  • Oxidation, condensation
  • Distil or reflux

Topics: WM, CD

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12
Q

Name the reagent(s) which could be used to esterify:

  • An alcohol
  • A phenol
A

Alcohol: carboxylic acid, acid anhydride, acyl chloride

Phenol: acid anhydride

Topics: WM, PL

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13
Q
  • What is the name of the reaction between an alcohol and a carboxylic acid to produce an ester?
  • What mechanism occurs?
  • State the conditions required.
A
  • Esterification
  • Nucleophilic substitution
  • Conc. H2SO4 or conc. HCl

​Topics: WM, PL

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14
Q
  • What is the name of the reaction between an alcohol and an acid anhydride to produce an ester?
  • What is the other organic product?
  • What mechanism occurs?
A
  • Esterification
  • Carboxylic acid
  • Nucleophilic substitution

Topics: WM, PL

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15
Q
  • What is the name of the reaction between a phenol and an acid anhydride to produce an ester?
  • What is the other organic product?
  • What mechanism occurs?
  • State the conditions required.
A
  • Esterification
  • Carboxylic acid
  • Nucleophilic substitution
  • Alkali, e.g. NaOH

Topics: WM, PL

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16
Q
  • What is the name of the reaction between an alcohol and an acyl chloride to produce an ester?
  • What mechanism occurs?
A
  • Esterification
  • Nucleophilic substitution

​Topics: WM, PL

17
Q
  • Give the reactant(s) required for the conversion of an ester to an alcohol.
  • Name the other organic product.
  • What is the name of this reaction?
  • What mechanism occurs?
  • State the conditions required.
A
  • a) Ester, water or b) ester, NaOH
  • a) Carboxylic acid or b) carboxylate ion
  • Ester hydrolysis
  • Nucleophilic substitution
  • a) HCl or H2SO4 or b) none

Topic: PL

18
Q
  • Give the reactant(s) required for the conversion of an amine to a secondary amide.
  • What mechanism occurs?
A
  • Amine, acyl chloride
  • Nucleophilic substitution

Topic: PL

19
Q
  • Give the reactant(s) required for the conversion of a diamine to a nylon (polyamide).
  • What is the name of this reaction?
  • What mechanism occurs?
A
  • Diamine, dicarboxylic acid or diamine, diacyl dichloride
  • Condensation, substitution
  • Nucleophilic substitution

Topic: PL

20
Q
  • Give the reactant(s) required for the conversion of a primary amide to a) a carboxylic acid, and b) a carboxylate ion.
  • Name the other organic product.
  • What is the name of this reaction?
  • What mechanism occurs?
  • State the conditions required.
A
  • a) Primary amide, water, HCl or H2SO4 or b) primary amide, NaOH
  • a) Ammonium or b) Ammonia
  • Hydrolysis
  • Nucleophilic substitution
  • Reflux

Topic: PL

21
Q
  • Give the reactant(s) required for the conversion of a secondary amide to a) a carboxylic acid, and b) a carboxylate ion.
  • Name the other organic product.
  • What is the name of this reaction?
  • What mechanism occurs?
  • State the conditions required.
A
  • a) Secondary amide, water, HCl or H2SO4 or b) secondary amide, NaOH
  • a) Amine salt or b) amine
  • Hydrolysis
  • Nucleophilic substitution
  • Reflux

Topic: PL

22
Q
  • Give the reactant(s) required for the conversion of an aldehyde or a ketone to a cyanohydrin.
  • What mechanism occurs?
A
  • Aldehyde or ketone, CN- (cyanide) ion
  • Nucleophilic addition

Topic: CD

23
Q
  • Give the reactant(s) required for the conversion of an aromatic amine to a diazonium salt.
  • What is the name of this reaction?
  • State the conditions required.
A
  • Aromatic amine, NaNO2 (sodium nitrate(III))
  • Diazotisation
  • Aromatic amine dissolved in dilute HCl, temperature below 5oC

Topic: CD

24
Q
  • Give the reactant(s) required for the conversion of a diazonium salt to an azo compound.
  • What is the name of this reaction?
  • What mechanism occurs?
  • State the conditions required.
A
  • Diazonium salt, coupling agent: phenol or aromatic amine
  • Coupling
  • Electrophilic substitution
  • Solution of diazonium salt should be ice-cold

Topic: CD

25
Q
  • Give the reactant(s) required for the conversion of benzene to bromobenzene.
  • What is the name of this reaction?
  • What mechanism occurs?
  • State the conditions required.
A
  • Benzene, bromine
  • Bromination
  • Electrophilic substitution
  • Reflux, FeBr3 (or form FeBr3 in situ from Fe)

​Topic: CD

26
Q
  • Give the reactant(s) required for the conversion of benzene to chlorobenzene.
  • What is the name of this reaction?
  • What mechanism occurs?
  • State the conditions required.
A
  • Benzene, chlorine
  • Chlorination
  • Electrophilic substitution
  • Anhydrous AlCl3

​Topic: CD

27
Q
  • Give the reactant(s) required for the conversion of benzene to nitrobenzene.
  • What is the name of this reaction?
  • What mechanism occurs?
  • State the conditions required.
A
  • Benzene, conc. HNO3
  • Nitration
  • Electrophilic substitution​
  • Conc. H2SO4, below 55oC

Topic: CD

28
Q
  • Give the reactant(s) required for the conversion of benzene to benzenesulfonic acid.
  • What is the name of this reaction?
  • What mechanism occurs?
  • State the conditions required.
A
  • Benzene, H2SO4
  • Sulfonation
  • Electrophilic substitution​
  • Reflux

Topic: CD

29
Q
  • Give the reactant(s) required to add an alkyl group to benzene.
  • What is the name of this reaction?
  • What mechanism occurs?
  • State the conditions required.
A
  • Benzene, chloroalkane
  • Friedel-Crafts alkylation
  • Electrophilic substitution​
  • Reflux, anhydrous AlCl3

Topic: CD

30
Q
  • Give the reactant(s) required to add an acyl group to benzene.
  • What is the name of this reaction?
  • What mechanism occurs?
  • State the conditions required.
A
  • Benzene, acyl chloride
  • Friedel-Crafts acylation
  • Electrophilic substitution​
  • Reflux, anhydrous AlCl3

Topic: CD

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