Organic synthesis Flashcards by Molly Flitcroft

Exam technique for answering synthesis questions?

6 steps?

Identify functional groups
Look for difference between start and end molecules of the pathway and deduce how they might have happened
Identify reagents that will add or remove atoms/groups of atoms to account for the differences
Identify conditions for said reagents
Use nature of reagent eg: nucleophile to decide on type of mechanism/reaction
Don’t forget other products of reactions

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Give the reagent needed to form an alkane from an alkene

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Give the reagent needed to form a haloalkane from an alkane

A halogen (X2)

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Give the conditions needed to form an alkane from an alkene

Over Nickel catalyst

At 200*C

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Give the conditions needed to form a haloalkane from an alkane
1

UV light

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Give the reagent needed to form a haloalkane from an alkene?

Halogen halide (HX)

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Give the conditions needed to form a haloalkane from an alkene?
1

Room temperature

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Name the type of reaction to form a haloalkane from an akene

Nucleophilic Addition

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Name the type of reaction to form a haloalkane from an alkane

Free Radical Substitution

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Name the type of reaction to form an alkane from an alkene

Free Radical/Catalytic Addition

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Give the reagent needed to form an amine from a haloalkane

Conc. NH3

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Give the conditions needed to form an amine from a haloalkane
2

Heat

in a sealed tube

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Name the type of reaction to form an amine from a haloalkane

Nucleophilic Substitution

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Give the reagent needed to form a nitrile from a haloalkane

KCN

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Give the conditions needed to form a nitrile from a haloalkane
3

Ethanolic solution
Reflux
Heat

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Name the type of reaction to from a nitrile from a haloalkane

Nucleophilic Substitution

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Give the reagent needed to form an amide from an amine

Acyl chloride or acid anhydride

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Give the conditions needed to form an amide from an amine

Reflux

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Name the type of reaction to form an amide from an amine

Acylation

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Give the reagent needed to form an amine from a nitrile

or LiAlH4

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Give the conditions needed to form an amine from a nitrile

Nickel catalyst

200*C

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Name the type of reaction to form an amine from a nitrile

Reduction / Electrophilic addition

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Give the reagent needed to form an alcohol from a haloalkane

NaOH (aq)

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Give the conditions needed to form an alcohol from a haloalkane
2

Reflux, warm

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Name the type of reaction to from an alcohol from a haloalkane

Nucleophilic Substitution

Give the reagent needed to form an alkene from a haloalkane

Conc. KOH

Give the conditions needed to form an alkene from a haloalkane 2

Hot | Ethanolic

Name the type of reaction to form an alkene from a haloalkane

Elimination

Give the reagent needed to form an alkene from an alcohol

Conc. H2SO4

Give the conditions needed to form an alkene from an alcohol | 2

Reflux, 180*C

Name the type of reaction to form an alkene from an alcohol

Elimination

Give the reagent needed to form an alcohol from an alkene

Conc, H3PO4

Give the conditions needed to form an alcohol from an alkene | 3

``` Steam High temp (300*C) High pressure (60 atm) ```

Name the type of reaction to form an alcohol from an alkene

Electrophilic Addition

Give the reagent/conditions needed to form an alkyl hydrogensulphate from an alkene

Conc, H2SO4

Name the type of reaction to form an alkyl hydrogensulphate from an alkene

Addition

Give the reagent/conditions needed to form an alcohol from an alkyl hydrogensulphate

H2O | Warm

Give the reagent needed to form an aldehyde from a primary alcohol

K2Cr2O7

Give the conditions needed to form an aldehyde from a primary alcohol 3 distill or reflux?

H+ so need H2SO4 Heat Distill

Name the type of reaction to form an aldehyde from a primary alcohol

Oxidation

1. Give the reagent needed to form a primary alcohol from an aldehyde

Aqueous NaBH4

1. Give the conditions needed to form a primary alcohol from an aldehyde

heat | ethanolic

Name the type of reaction to form a primary alcohol from an aldehyde

Reduction

Give the reagent needed to form a ketone from a secondary alcohol

K2Cr2O7

Give the conditions to form a ketone from a secondary alcohol 3 distill or reflux?

H+ so need H2SO4 Heat Reflux

Name the type of reaction to form a ketone from a secondary alcohol

Oxidation

1. Give the reagent needed to form a secondary alcohol from a ketone

NaBH4

2. Give the conditions needed to form a primary alcohol from an aldehyde

dry ether

1. Give the conditions needed to form a secondary alcohol from a ketone

heat | ethanolic

2. Give the reagent needed to form a secondary alcohol from a ketone

LiAlH4

2. Give the conditions needed to form a secondary alcohol from a ketone

dry ether

Give the reagent/conditions needed to form a 2-hydroxynitrile from a ketone

HCN

Name the type of reaction to form a 2-hydroxynitrile from a ketone

Nucleophilic addition

Give the reagent needed to form a carboxylic acid from an aldehyde 3 options

``` K2Cr2O7 or Tollens reagent or Fehlings solution ```

Give the conditions needed to form a carboxylic acid from an aldehyde 3

Heat Reflux H+ so needs H2SO4

Name the type of reaction to form a carboxylic acid from an aldehyde

Oxidation

Give the reagent needed to form an ester from a carboxylic acid

Alcohol

Give the conditions needed to form an ester from a carboxylic acid

Conc H2SO4

Name the type of reaction to form an ester from a carboxylic acid

Esterification

Give the reagent needed to form a carboxylic acid from an ester 2 options

H+ or OH- | so acid eg: H2SO4 or an alcohol

Give the conditions needed to form a carboxylic acid from an ester

Reflux

Name the type of reaction to form a carboxylic acid from an ester

Hydrolysis

Give the reagents needed to form an ester from an alcohol | 3

``` Carboxylic acid or Acyl chloride or Acid anhydride ```

Give the conditions needed to form an ester from an alcohol

Conc H2SO4

Name the type of reaction to form an ester from an alcohol

Esterification

Give the reagents needed to form an amide from an acyl chloride

NH3 or 1*/2* amine

Name the type of reaction to form an amide from an acyl chloride

nucleophilic substitution

Give the reagents and conditions needed to form an ester from an acid anhydride

Alcohol | H+

Name the type of reaction to form an ester from an acid anhydride

esterification

Give the reagents needed to form a hydroxynitrile from an aldehyde

NaCN(aq) / H+(aq)

name the type of reaction to form a hydroxynitrile from an aldehyde

Nucleophilic addition

Give the reagents and conditions needed to form a carboxylic acid from an acyl chloride

warm water with H+ or OH-

Give the conditions needed to form an acyl chloride from a carboxylic acid

SOCl2

Give the reagent needed to form a carboxylic acid from a nitrile

Acid/ H+(aq)

Name the type of reaction to form a carboxylic acid from a nitrile

Acid hydrolysis

Give the reagent needed to form cyclohexane from benzene

Give the conditions needed to form cyclohexane from benzene

Nickel catalyst | 150*C

Name the reaction to form cyclohexane from benzene

Reduction

give the reagents needed to form nitrobenzene from benzene

conc HNO3 | conc H2SO4

give the conditions needed to form nitrobenzene from benzene

50*C

Name the reaction to form nitrobenzene from benzene

Electrophilic substitution | nitration

Give the reagents and conditions needed to form phenylamine from nitrobenzene

NaOH conc H2SO4 Sn catalyst

Name the type of reaction to form pheylamine from nitrobenzene

Reduction

Give the reagent needed to form N-phenylethanamide from phenylamine

Ethanoyl Chloride

Name the type of reaction to form N-phenylethanamide from phenylamine

Acylation

Give the reagents and conditions needed to form phenylethene from benzene

CH3CH2O | AlCl3 catalyst

Name the type of reaction to form phenylethene from benzene

Electrophlic substitution (friedel-crafts acylation) then catalytic dehydrogenation

Give the conditions needed to form polystyrene from phenylethene

Ziegler catalyst

Name the reaction to form polystyrene from phenylethene

Polymerisation

Give the reagents and conditions needed to form methylpheylketone from benzene

HCOCl AlCl3 catalyst 40*C

Name the type of reaction to form methylphenylketone from benzene

``` Electrophilic substitution (friedel-crafts acylation) ```

Give the reagents and conditions to form methylbenzene from benzene

RCl AlCl3 catalyst 40*C

Name the reaction to form methylbenzene from benzene

``` Electrophilic substitution (friedel-crafts alkylation) ```

Organic synthesis Flashcards

(93 cards)