Synthetic Routes Flashcards

1
Q

Alkane to haloalkane

A

Free radical substitution
Br2, Cl2, etc
UV light

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2
Q

Haloalkane to alcohol

A

Nucleophilic substitution
Aqueous KOH or NaOH
Heat under reflux

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3
Q

Haloalkane to nitrile

A

Nucleophilic substitution
Heat under reflux with KCN dissolved in ethanol

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4
Q

Haloalkane to primary amine to secondary amine

A

Nucleophilic substitution
Heat under reflux with (excess) NH3 dissolved in alcohol

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5
Q

Haloalkane to alkene

A

Elimination
Heat under reflux with ethanolic KOH

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6
Q

Alkene to polyalkene

A

High pressure
Catalyst

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7
Q

Alkene to haloalkane

A

Electrophilic addition
HCl, HBr
Room temp

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8
Q

Alkene to dihalogenoalkane

A

Electrophilic addition
Cl2, Br2
Room temp

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9
Q

Dihalogenoalkane to diol

A

Nucleophilic substitution
Aqueous KOH
Heat under reflux

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10
Q

Alcohol to alkene

A

conc. H2SO4 or conc. H3PO4
Elimination, dehydration

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11
Q

Alkene to alcohol

A

Step 1: Electrophilic addition with H2SO4
Step 2: H2O warm hydrolysis

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12
Q

partial oxidation of primary alcohol

A

acidified potassium dichromate (VI) solution
heat and distill
aldehyde forms

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13
Q

complete oxidation of primary alcohol

A

acidified potassium dichromate (VI) solution
heat under reflux
carboxylic acid forms

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14
Q

oxidation of secondary alcohol

A

heat with acidified potassium dichromate (VI) solution
forms ketone

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15
Q

why can’t tertiary alcohols not be oxidised

A

there is no H atom attached to the carbon with the -OH group

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16
Q

aldehyde to alcohol
what type of alcohol forms

A

reduction with sodium borohydride (NaBH4)
nucleophilic addition
primary alcohol

17
Q

ketone to alcohol
what type of alcohol forms

A

reduction with sodium borohydride (NaBH4)
nucleophilic addition
secondary alcohol

18
Q

alcohol to ester

A
19
Q

aldehyde to hydroxynitrile
why does this form enantiomers

A

nucleophilic adition
NaCN and H2SO4

19
Q

ketone to hydroxynitrile
when/why would this form enantiomers?

A
20
Q

carboxylic acid to ester

A

heat with alcohol in the presence of H2SO4 catalyst
esterficiation

21
Q

Acyl chloride/acid anhydride to ester

A

alcohol
room temp
nucleophilic addition-elimination

22
Q

Acyl chloride/acid anhydride to carboxylic acid

A

H2O
room temp
nucleophilic addition-elimination

23
Q

Acyl chloride/acid anhydride to secondary amide

A

primary amine
room temp
nucleophilic addition-elimination

24
Q

Acyl chloride/acid anhydride to primary amide

A

NH3
room temp
nucleophilic addition-elimination

25
Q

hazards of using KCN / HCN

A
26
Q

benzene

mechanism

A

electrophilic substitution

Nitration
-conc HNO3 and conc H2SO4
heat under reflux at 50 degrees Celsius
-yellow dry nitrobenzene forms

Friedel-Crafts Acylation
heat under reflux at 50 degrees Celsius
reated with alkyl or acyl halides in the presence of a strong Lewis acid (e.g. AlCl3). These are known as Friedel Crafts reactions and are examples of electrophilic aromatic substitution reactions.