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Organic Chemistry > Organic Synthesis > Flashcards

Organic Synthesis Flashcards

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1
Q

What mechanism do alkanes undergo?

A

free radical substitution

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2
Q

What mechanism do alkenes undergo?

A

electrophilic addition

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3
Q

What mechanism do alcohols and haloalkanes undergo?

A

nucleophilic substitution

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4
Q

alkane –> haloalkane

A

reagent: halogen
conditions: UV light
reaction: free radical substitution

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5
Q

alkene –> alkane

A

reagent: H2(g)
conditions: Ni catalyst/423K (high temp)
reaction: addition/hydrogenation

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6
Q

alkene –> haloalkane

A

reagent: halogen OR hydrogen halide
conditions: room temperature
reaction: electrophilic addition/halogenation

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7
Q

alkene –> alcohol

A

reagent: H20(g)
conditions: H3PO4 catalyst
reaction: electrophilic addition/hydration

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8
Q

1° alcohol –> aldehyde

A

reagent: K2Cr2O7
conditions: dilute H2SO4/heat and distil
reaction: oxidation

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9
Q

1° alcohol –> carboxylic acid

A

reagent: K2Cr2O7
conditions: dilute H2SO4/heat under reflux
reaction: oxidation

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10
Q

2° alcohol –> ketone

A

reagent: K2Cr2O7
conditions: dilute H2SO4/heat under reflux
reaction: oxidation

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11
Q

alcohol –> alkene

A

conditions: conc H2SO4 or H3PO4
reaction: elimination/dehydration

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12
Q

alcohol –> haloalkane

A

reagent: hydrogen halide made in situ
NaX + H2SO4 –> HX + NaHSO4
conditions: heat under reflux
reaction: nucleophilic substitution

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13
Q

1° haloalkane –> alcohol

A

reagent: NaOH(aq) or H2O(aq)
conditions: heat under reflux
reaction: nucleophilic substitution/hydrolysis (if water in used as a nucleophile)

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14
Q

what mechanisms do aromatic compounds undergo?

A

electrophilic substitution

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15
Q

2,4,6 directing groups

A

activating groups:
NH2
NHR

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16
Q

3,5 directing groups

A

deactivating groups:
OH
NO2

17
Q

aldehyde –> 1° alcohol

A

reagents: NaBH4(aq)
reaction: nucleophilic addition

18
Q

ketone –> 2° alcohol

A

reagents: NaBH4(aq)
reaction: nucleophilic addition

19
Q

carbonyl –> hydroxynitrile

A

reagents: 2NaCN + H2SO4 –> 2HCN + Na2SO4 (in situ)
reaction: nucleophilic addition

20
Q

what reactions do carboxylic acids undergo?

A
  • redox (with metals)
  • neutralisation (with bases)
  • forms carboxylate ions and salts
21
Q

carboxylic acid + metal

A

–> metal carboxylate + hydrogen

butanoic acid + Mg –> magnesium butanoate + H2

22
Q

carboxylic acid + metal oxide

A

–> metal carboxylate + water

butanoic acid + CaO –> calcium butanoate + H2O

23
Q

carboxylic acid + alkali

A

–> carboxylate salt + water

butanoic acid + NaOH –> sodium butanoate + H2O

24
Q

carboxylic acid + metal carbonate

A

–> carboxylate salt + carbon dioxide + water

butanoic acid + MgCO3 –> magnesium butanoate + CO2 + H2O

25
Q

carboxylic acid –> acid anhydride

A

two carboxylic acids undergo hydrolysis (one OH group removed and the H from the other OH group)

26
Q

esterification

A

carboxylic acid + alcohol –> ester

(alcohol-yl carboxylic acid-oate)

warm with conc H2SO4

27
Q

acid hydrolysis of esters

A

ester + water –> carboxylic acid + alcohol

heat with a dilute aqueous acid

28
Q

alkaline hydrolysis of esters

A

ester + alkali –> carboxylate salt + alcohol

IRREVERSIBLE

29
Q

carboxylic acid –> acyl chloride

A

carboxylic acid + SOCl2 (thionyl chloride) –> acyl chloride + SO2(g) + HCl(g)

propanoic acid + SOCl2 –> propanoyl chloride

(more reactive than carboxylic acids)

30
Q

acyl chloride –> ester

A

acyl chloride + alcohol –> ester + HCl

ethanoyl chloride + methanol –> methyl ethanoate + HCl

31
Q

acyl chloride –> carboxylic acid

A

acyl chloride + water –> carboxylic acid + HCl

ethanoyl chloride + water –> ethanoic acid + HCl

32
Q

acyl chloride –> 1° amide

A

acyl chloride + ammonia –> primary amide + ammonium chloride

ethanoyl chloride + 2NH3 –> ethanamide + NH4Cl

(can form a 2° and 3° amide by reacting with 1° and 2° amines)

33
Q

acid anhydride –> carboxylic acid

A

acid anhydride + alcohol –> carboxylic acid + ester

Organic Chemistry (4 decks)

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