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A Level - Chemistry > Organic synthesis > Flashcards

Organic synthesis Flashcards

1
Q

What are the features of homologus series you should learn?

A

Functional group

Properties

Typical reactions

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2
Q

What are the features of alkanes?

A

C-C

Non-polar and unreactive

Radical substitution

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3
Q

What are the features of alkenes?

A

C=C

Non-polar, electron-rich double bond

Electrophilic addition

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4
Q

What are the features of aromatic compounds?

A

C6H5-

Stable delocalsied ring of electrons

Electrophilic substitution

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5
Q

What are the features of an alcohol?

A

Polar C-OH bond

Nucleophillic substitution and dehydration/elimination

OR Lone pair on O acts a nucleophile

Esterification and nucleophilic substitution

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6
Q

What are the features of halogenoalkane?

A

C-X

Polar C-X bond

Nucleophilic substitution or elimination

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7
Q

What are the features of amines?

A

C-NH2 or C-NR2

Lone pair on N is basic and can act as nucleophile

Neutralisation and nucleophilic substitution

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8
Q

What is the functional group of an amide?

A

-CONH2 or -CONHR

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9
Q

What are the properties of nitriles?

A

C-C≡N

Electron deficient carbon centre

Reduction or hydrolysis

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10
Q

What are the featrures of aldehydes/ketones? (carbonyls)

A

C=O

Polar C=O bond

Nucleophilic addition or reduction and aldehydes will oxidise

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11
Q

What are the features of carboxylic acids?

A

-COOH

Electron deficient carbon centre

Neutralisation or esterification or reduction

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12
Q

What are the features of an ester?

A

RCOOR’

Electron deficient carbon centre

Hydrolysis

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13
Q

What are the features of an acyl chloride?

A

-COCl

Electron deficient carbon centre

Nucleophilic addition-elimination or condensation (loses HCl) or Friedel-Crafts reaction

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14
Q

What is a synthetic route?

A

Way in which you react things in different steps to form the desired product

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15
Q

What should be included if exams ask you how to make compound from another in the exam?

A

Special procedures (e.g. refluxing)

Conditions needed (tempreature or catalyst)

Safety precautions (do in a fume cupboard)

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16
Q

What two things should be remembered in a synthetic route?

A

Stereoisomers

Safety

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17
Q

Why is making the correct stereoisomers imporant?

A

Different stereoisomers could have different properties

Mechanisms can cause different ones to form

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18
Q

What are the conditions of thermal cracking and what are the products?

A

1000ºC

70 atm

Long-chain alkanes → mostly alkenes

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19
Q

What are the conditions of catalytic cracking and what are the products?

A

500ºC

Slight pressure

Zeolite catalyst (hydrated aluminosilicate)

Long-chain alkanes → smaller aromatic hydrocarbons

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20
Q

What is reforming and what are the conditions?

A

Conversion of straight chain → cyclic → aromatic hydrocarbons

500ºC

Platinum catalyst

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21
Q

What is hydrogenation and conditions?

A

Alkene + H2 → Alkane

150ºC

Nickle catalyst

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22
Q

How do you convert an alkene to a diol?

A

Acidified KMnO4

20ºC

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23
Q

How do you convert an alkene to a dihalogenoalkane?

A

X2

20ºC

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24
Q

How do you convert an alkene to an alkane?

(hydrogenation reaction)

A

H2

Nickel catalyst

150ºC

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25
Q

How do you convert an alkene into an alcohol?

(hydration)

A

Steam

H3PO4 catalyst

300ºC

60-70 atm

26
Q

How do you convert an alcohol to an alkene?

A

conc H3PO4

170ºC

27
Q

How do you convert an alkene to a halogenoalkane?

28
Q

How do you convert a halogenoalkane to an alkene?

A

KOH

Ethanol

Reflux

29
Q

How do you convert an alkane to a halogenoalkane?

A

X2

UV light

30
Q

How do you convert a halogenoalkane to an alcohol?

A

warm aqueous KOH + reflux

OR Mg, dry ether, carbonyl then dilute acid

31
Q

How do you convert an alcohol into a halogenoalkane?

A

KBr, 50% H2SO4 at 20ºC for bromoalkane

PCl5, 20ºC OR HCl 20ºC for chloroalkane

Red phosphorus + Iodine refluxed in situ then distilled for iodoalkane

32
Q

How do you convert an alcohol to an ester?

A

Carboxylic acid, acid catalyst and heat

OR acyl chloride

33
Q

How do you convert an ester to an alcohol?

A

Dilute acid or alkali

Reflux

34
Q

How do you convert a halogenoalkane to a nitrile?

A

KCN

Ethanol

Reflux

35
Q

How do you convert a halogenoalkane to a carboxylic acid?

A

Mg, dry ether then CO2 then dilute acid

36
Q

How do you convert a halogenoalkane to a primary amine?

A

XS ethanolic ammonia

Heat

37
Q

How do you convert a primary amine to a more substituted amine?

A

Halogenoalkane

38
Q

How do you convert a nitrile to a primary amine?

A

LiAlH4 then dilute acid

OR H2, Ni/Pt catalyst, high temp and pressure

39
Q

How do you convert a nitrile to a carboxylic acid?

A

Dilute HCl

Reflux

40
Q

How do you convert an alcohol to an iodoalkane?

A

Red phosphorus and I2 to make PI3 in situ

Reflux

41
Q

How do you convert a primary alcohol into an aldehyde?

A

K2Cr2O7 & H2SO4

Heat

Distil for aldehydes

42
Q

How do you convert a secondary alcohol into a ketone?

A

K2Cr2O7 + H2SO4

Reflux

43
Q

How do you convert an aldehyde into a carboxylic acid?

A

K2Cr2O7 & H2SO4

Reflux

44
Q

How do you convert a methyl ketone (RCOCH3) into a carboxylic acid?

A

I2 & NaOH

20ºC

45
Q

How do you convert a carboxylic acid into a primary alcohol?

46
Q

How do you convert an aldehyde or ketone into the hydroxynitrile?

A

KNC & H+

OR HCN & ethanol at reflux

47
Q

How do you convert an ester to a carboxylic acid?

A

Dliute acid or alkali

Reflux

48
Q

How do you convert a carboxylic acid to an ester?

A

Alcohol

Acid catalyst

Heat

49
Q

How do you convert a carboxylic acid to an acyl chloride?

A

PCl5

20ºC

50
Q

How do you convert an acyl chloride into a carboxylic acid?

51
Q

How do you convert an acyl chloride into an ester?

A

Alcohol

20ºC

52
Q

How do you convert an acyl chloride to make a primary amide?

53
Q

How do you convert an acyl chloride to make an N-substituted amide?

A

Primary amine

20ºC

54
Q

How do you convert a benzene ring into a halobenzene?

A

X2

Halogen carrier

20ºC

55
Q

What are the halogen carriers?

A

Aluminium halides

Iron halides

Iron

56
Q

How do you convert benzene to a phenylketone?

A

Acyl chloride

AlCl3 catalyst

Reflux

57
Q

How do you convert benzene into an alkyl benzene?

A

Halogenoalkane

AlCl3 catalyst

Reflux

58
Q

How do you convert benzene into nitrobenzene?

A

conc HNO3 & conc H2SO4

Below 55ºC

59
Q

How do you convert nitrobenzene into phenylamine?

A

Tin & conc HCl under reflux

Then NaOH

60
Q

How do you convert a phenol to 2,4,6-tribromophenol?

A

Bromine water

20ºC

A Level - Chemistry (26 decks)

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