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28) Organic synthesis Flashcards

1
Q

What is a nitrile group?

A

-CN

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2
Q

haloalkane + NaCN or KCN (in ethanol ->

A

nitrile + Na halide or K halide

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3
Q

In the nucleophilic substitution mechanism for the formation of a nitrile, where are the 2 curly arrows?

A

from the :C- triple bond N to the partially positive carbon

from the carbon - halogen bond to the partially negative halgogen

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4
Q

aldehyde/ketone + HCN ->

A

hydroxynitrile (cyanohydrin)

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5
Q

In the nucleophilic addition mechanism for the formation of a hydroxynitrile, where are the 4 curly arrows?

A

from the :C- triple bond N to the partially positive carbon
from the C=O bond to the partially negative O

from the negative :O- to the partially positive H of a water molecule
from the H-O bond of the water molecule to the partially negative O of the water molecule

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6
Q

Give an equation for the reduction of a nitrile and state the catalyst

A

nitrile + 2H2 -> amine

Ni catalyst

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7
Q

Give an equation for the hydrolysis of a nitrile and the conditions required

A

nitrile + dilute aqueous acid -> carboxylic acid

heat

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8
Q

Name two methods of forming carbon-carbon bonds to benzene rings

A

alkylation and acylation

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9
Q

Define alkylation

A

reaction that transfers an alkyl group from a haloalkane to a benzene ring, taking place in the presence of a Friedel-Crafts catalyst

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10
Q

Define acylation

A

reaction of benzene with an acyl chloride in the presence of an aluminium chloride catalyst to form a ketone

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11
Q

Define filtration under reduced pressure

A

technique for separating a sold product from a solvent or liquid reaction mixture

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12
Q

State 5 key pieces of equipment need to carry out filtration under reduced pressure

A 
Buchner flask
Buchner funnel
pressure tubing
filter paper
access to filter or vacuum pump
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13
Q

Define recrystallisation

A

technique to remove impurities from the solid product obtained after filtration (using the minimum volume of hot solvent)

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14
Q

Define melting point determination

A

technique to identify whether a solid compound is pure

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15
Q

State a feature of a pure sample

A

very sharp melting range

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16
Q

Define melting range

A

difference between temperature at which the sample begins to melt and at which melting is complete

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17
Q

Describe the 2 features of a sample containing impurities

A

wide melting range

lower melting point

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18
Q

Describe the key steps of melting point determination

A

seal capillary tube (using Bunsen burner flame)
fill with dry, free-flowing crystals
take melting point by using electrically heated melting point apparatus or an oil bath / Thiele tube method

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19
Q

Describe the steps of using an electrically heated melting point apparatus

A

using a thermometer and rapid heat setting observe the sample through magnifying window
record melting point + allow apparatus to cool
using a second sample, set to low and raise temp slowly as melting point is approached for accurate determination of melting point

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20
Q

Describe the steps of using an oil bath / Thiele tube method

A

set up
attach capillary tube with sample to thermometer
insert/clamp thermometer
slowly heat using a micro-burner, when the solid starts to melt, remove heat and record temperature

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21
Q

alkane -> haloalkane

A

hydrogen halide

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22
Q

alkane -> primary alcohol

A

hydration

H3PO4/H2O

23
Q

haloalkane -> primary alcohol

24
Q

haloalkane -> nitrile

25
Q

haloalkane -> amine

A

NH3 / ethanol

26
Q

nitrile -> amine

A

H2/Ni

reduction

27
Q

nitrile -> carboxylic acid

A

H2O/HCl

hydrolysis

28
Q

primary alcohol -> alkane

29
Q

primary alcohol -> haloalkane

A

sodium halide / H2SO4

30
Q

primary alcohol -> aldehyde

A

K2Cr2O7/H2SO4

oxidation

31
Q

primary alcohol -> ester

A

carboxylic acid / H2SO4

esterification

32
Q

aldehyde -> primary alcohol

A

NaBH4/H2O

reduction

33
Q

aldehyde -> hydroxynitrile

A

NaCN/H+

nucleophilic addition

34
Q

aldehyde -> carboxylic acid

A

K2Cr2O7/H+

oxidation

35
Q

carboxylic acid -> ester

A

alcohol / H2SO4

esterification

36
Q

carboxylic acid -> acyl chloride

37
Q

ester -> carboxylic acid

A

dilute acid hydrolysis

38
Q

ester -> sodium salt of carboxylic acid + alcohol

A

NaOH(aq)

alkaline hydrolysis

39
Q

acyl chloride -> ester

40
Q

acyl chloride -> carboxylic acid

41
Q

acyl chloride -> primary amide

42
Q

acyl chloride -> secondary amide

A

primary amide

43
Q

benzene -> methylbenzene

A

CH3Cl/AlCl3

alkylation

44
Q

benzene -> nitrobenzene

A

HNO3/H2SO4

nitration

45
Q

benzene -> bromobenzene

A

Br2/FeBr3

bromination

46
Q

benzene -> chlorobenzene

A

Cl2/AlCl3

chlorination

47
Q

benzene -> phenylethanone

A

CH3COCl/AlCl3

acylation

48
Q

nitrobenzene -> phenylamine

A

Sn/HCl

reduction

49
Q

phenylamine -> 2,4,6-tribromophenylamine

50
Q

phenylethanone -> 1-phenylethanol

A

NaBH4

reduction

51
Q

phenol -> 2,4,6-tribromophenol (white ppt.)

A

Br2

bromination

52
Q

phenol -> sodium phenoxide

A

NaOH(aq)

neutralisation

53
Q

phenol -> mixture of 4-nitrophenol and 2-nitrophenol

A

HNO3

nitration

54
Q

What is an ether?

Chemistry (31 decks)

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