organic synthesis Flashcards

1
Q

Carbon-carbon bond formation

A

Important as they provide a way of creating new compounds with more carbon atoms

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2
Q

Nitriles from haloalkanes

A

Formed by reacting haloalkanes with sodium cyanide (NaCN) or potassium cyanide in ethanol, in this reaction the length of the carbon chain increases. This is nucleophilic substitution. Possible reaction =CH3CH2Cl + KCN –> CH3CH2CN + KCl

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3
Q

Nitriles from aldehydes and ketones

A

Aldehydes and ketones will with react with HCN. However, HCN is too poisonous to use so instead a mixture of NaCN and sulfuric acid is used, to improve safety and reaction rate
CH3COCH3 + HCN –> CH3C(OH)(CN)CH3

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4
Q

Reduction of nitriles

A

Nitriles can be reduced to amines by reacting with hydrogen in the presence of a nickel catalyst
CH3CN + 2H2 –> CH3CH2NH2

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5
Q

Hydrolyses of nitriles

A

Nitriles undergo hydrolyses to form carboxylic acids by heating with dilute aqueous acid i.e. HCl
CH3CN + 2H2O + HCl –> CH3COOH + NH4Cl

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6
Q

Alkylation of benzene rings

A

Alkylation is a reaction which transfers an alkyl group from a haloalkane to a benzene ring. The catalyst AlCl3 is needed, HCl is also produced

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7
Q

Alcylation of benzene rings

A

When a benzene ring reacts with an alcyl chloride in the presence of an aluminium chloride catalyst, a ketone is formed. HCl is also produced

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8
Q

Nitriles to carboxylic acid

A

H2O, HCl, heat

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9
Q

Acyl chloride to carboxylic acid

A

H2O

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10
Q

Aldehyde/ketone to alcohol

A

NaBH4

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11
Q

Alcohol to alkene

A

H2SO4 and heat

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12
Q

Haloalkane to alcohol

A

NaOH (aq)

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13
Q

Aldehyde/ketone to hydroxynitrile

A

NaCN(aq)/H+(aq)

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14
Q

Haloalkane to amine

A

NH3 in ethanol

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15
Q

Alcohol to haloalkane

A

Sodium halide and H2SO4

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16
Q

Acyl chloride to secondary amide

A

Primary amine

17
Q

Acyl chloride to primary amide

18
Q

Alkene to alcohol

A

H2O (steam) / H3PO4

19
Q

Ester to carboxylate salt

A

Hot aqueous alkali

20
Q

Alkene to alkane

A

H2/Ni 150 degreese

21
Q

Ester to carboxylic acid

A

Hot aqueous acid

22
Q

Carboxylic acid to ester

A

Alcohol / conc. H2SO4

23
Q

Nitrile to amine

24
Q

Haloalkane to nitrile

A

NaCN or KCN in ethanol

25
Alcohol to aldehyde
K2Cr2O7 / HSSO4 distil
26
Alcohol to ester
Carboxylic acid / conc. H2SO4 or acid anhydride or acyl chloride
27
Alcohol to carboxylic acid
K2Cr2O7 / H2SO4, reflux
28
Alkane to haloalkane
Halogen, UV
29
Acyl chloride to ester
Alcohol
30
Carboxylic acid to acyl chloride
SOCl2
31
Alkene to haloalkane
Hydrogen halide
32
How do you prepare a solid substance to be tested
Dissolve 5 grams of the substance in the minimum amount of hot water whilst stirring. Then filter it to remove the debris