WHOLE ORGANIC SYNTHESIS (LOL) Flashcards

1
Q

How to perform reflux and when is it used

A

if you need to heat volatile liquids so that reactants or products are not lost as they will evaporate and condense back into the flask

use a heating mantle if liquids are flammable to heat a round bottom flask that is attached to a condenser with water flowing upwards

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
2
Q

How to perform distillation and when is it used

A

used to separate substances with different boiling points, or to extract a chemical before it reacts any further

gently heat mixture using a heating mantle with a thermometer to control temperature, product will evaporate out and condense using a water condenser into a flask on the other side

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
3
Q

When is filtration used and how

A

used to separate solids from liquids

place a filter paper disc in a Buchner funnel and wet it to create a seal, place funnel on top of flask, then pour the mixture into the funnel with a vacuum line on to thoroughly separate the liquid out

vacuum creates reduced pressure which pulls the liquid through

solid can be recrystallized to purify further

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
4
Q

When is recrystallisation used and how to do it

A

used to purify solids using a very carefully chosen solvent

add just enough hot solvent to dissolve impure solid to give a SATURATED SOLUTION of impure product

allow solution to cool down which causes crystal formation

the impurities will remain dissolved in solution as they take longer to crystallise as there is less

then filter to get purified solid crystals and wash these with very cold solvent then dry crystals

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
5
Q

How to measure boiling point of substance and why

what values signify impurities

what is an issue with identifying boiling points

A

can help to detect impurities

can determine boiling point using distillation by gently heating and measuring temperature that it distils

then compare value to a data book which can signify impurities, higher boiling point or a range of temperatures shows impurities

some organic compounds have similar boiling points so other analytical techniques must be used

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
6
Q

Alkane functional group, properties and typical reactions

A

C-C

unreactive, non-polar bond

typically radical substitution

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
7
Q

Alkene functional group, properties and typical reactions

A

C=C

electron rich double bond, non-polar bond

typically electrophilic addition

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
8
Q

Alcohol functional group, properties and typical reactions

A

C-OH

lone pair on oxygen can act as nucleophile, Polar C-O bond

typically esterification and nucleophilic substitution or dehydration/elimination

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
9
Q

Aromatic compound functional group, properties and typical reactions

A

C6H5-

delocalised electron ring, stable compound

typically electrophilic substitution

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
9
Q

Aromatic compound functional group, properties and typical reactions

A

C6H5-

delocalised electron ring, stable compound

typically electrophilic substitution

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
10
Q

Haloalkane functional group, properties and typical reactions

A

C-X

polar C-X bond

typically nucleophilic substitution and elimination

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
11
Q

Nitrile functional group, properties and typical reactions

A

C-CN

electron deficient carbon centre

typically reduction and hydrolysis

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
12
Q

Amine functional group, properties and typical reactions

A

C-NH2

lone pair on N is basic, can act as a nucleophile

typically undergo nucleophilic substitution and neutralisation

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
13
Q

Aldehyde and ketone functional group, properties and typical reactions

A

C=O

polar C=O bond

typically undergo nucleophilic addition, oxidation, reduction

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
14
Q

Carboxylic acid functional group, properties and typical reactions

A

COOH

electron deficient carbon centre

typically esterification and neutralisation

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
15
Q

Ester functional group, properties and typical reactions

A

RCOOR

electron deficient carbon centre

typically undergo hydrolysis

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
16
Q

Acid anhydride functional group, properties and typical reactions

A

RCOOCOR

electron deficient carbon centre

typically esterification

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
17
Q

Acyl chloride functional group, properties and typical reactions

A

COCl

electron deficient carbon centre

nucleophilic addition-elimination, friedel crafts acylation

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
18
Q

What is an addition reaction and what functional groups can this occur in

A

double bond is broken and 2 molecules join to form a single product

C=C

C=O

COOH

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
19
Q

What is a substitution reaction and what functional groups can this occur in

A

A functional group is exchanged for another

C-X

C-OH

Benzenes

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
20
Q

What is an elimination/Dehydration reaction and what functional groups can this occur in

A

A double bond usually formed when functional group is removed and released as part of a smaller molecule

C-X eliminates HX

C-OH eliminates H2O

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
21
Q

What is a condensation reaction and what functional groups can this occur in

A

2 molecules join and a small molecule is released (H2O or H-Cl usually)

COCl

COOH

CONH2

C-OH

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
22
Q

What is a hydrolysis reaction and what functional groups can this occur in

A

2 smaller molecules are formed by splitting a larger one with water

polyamides, polyesters

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
23
Q

What is an oxidation reaction and what functional groups can this occur in

A

Gaining of oxygen or loss of a hydrogen (theoretically loss of electrons)

C-OH –> C=OH –> COOH

24
Q

What is a reduction reaction and what functional groups can this occur in

A

Normally loss of oxygen or gain of hydrogen (theoretically gain of electrons)

COOH –> C=OH –> C-OH

25
Q

Alcohol –> aldehyde

A

K2Cr2O7, H2SO4

heat primary alcohol under distillation

26
Q

Aldehyde –> alcohol

A

NaBH4 in methanol and water

27
Q

Aldehyde –> Carboxylic acid

A

K2CR2O7, H2SO4

heat under reflux

28
Q

Alcohol –> ketone

A

K2CR2O7, H2SO4

heat secondary alcohol under distillation

29
Q

Alcohol –> haloalkane

A

NaX, H2SO4

20 degrees

30
Q

Alcohol –> alkene

A

Conc H2SO4/H3PO4

heat

31
Q

Alkene –> alcohol

A

Steam, H3PO4 catalyst

60 atm

300 degrees

32
Q

Alkene –> dihaloalkane

A

X2

20 degrees

33
Q

Alkene –> haloalkane

A

HX

20 degrees

34
Q

Haloalkane –> alkene

A

KOH, ethanol

heat under reflux

35
Q

Haloalkane –> alcohol

A

Warm NaOH, H2O

heat under reflux

36
Q

Alkane –> haloalkane

A

X2

UV light

37
Q

ketone –> alcohol

A

NaBH4, methanol, water

38
Q

Alkene –> alkane

A

Hydrogen, Nickel catalyst

150 degrees

39
Q

Haloalkane –> primary amine

A

NH3

heat

40
Q

Haloalkane –> 2nd/3rd amine

A

NH3

heat

41
Q

Carboxylic acid –> ester

A

Alcohol, Conc H2SO4

heat

42
Q

COOH –> Acid chloride

A

SOCl2

43
Q

Acid chloride –> COOH

A

H2O

20 degrees

44
Q

Acid chloride –> ester

A

Alcohol

20 degrees

45
Q

Aldehyde/ketone –> Hydroxynitrile

A

KCN, H2SO4

20 degrees

46
Q

Hydroxynitrile/nitrile –> amine

A

LiAlH4 + dilute H2SO4

or

Hydrogen, nickel catalyst

high temp and pressure

47
Q

Haloalkane –> nitrile

A

KCN, ethanol

heat under reflux

48
Q

Acid chloride –> primary amide

A

NH3

20 degrees

49
Q

ester –> COOH

A

Dilute H2SO4, H2O

heat under reflux

or

NaOH

heat under reflux

50
Q

Benzene –> nitrobenzene

A

Nitration

Conc H2SO4 + HNO3

less than 55 degrees

51
Q

Nitrobenzene –> phenylamine

A

Reduction

Conc HCl, Sn

heat under reflux with NaOH

52
Q

Benzene –> Phenylketone

A

Acylation

Acyl chloride, AlCl3 catalyst, heat under reflux in anhydrous conditiions

53
Q

Benzene –> Halobenzene

A

Halogenation

X2, AlCl3 catalyst in warm conditions

54
Q

Benzene –> alkylbenzene

A

Alkylation

Haloalkane, AlCl3 catalyst

heat under reflux

55
Q

Phenol –> sodium phenoxide

A

NaOH

20 degrees

56
Q

Phenol –> 2,4,6 tribromophenol

A

Br2

20 degrees

57
Q

Phenol –> Phenyl ester

A

Acyl chloride

20 degrees