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chemistry > topic 17,1-4- further organic > Flashcards

topic 17,1-4- further organic Flashcards

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1
Q

what is an arene

A

ring compounds in which there are delocalised electrons

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2
Q

aromatic compounds

A

the bonding in a compound which has delocalized elctrons forming π bonding in a hydrocarbon ring

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3
Q

aliphatic molecules

A

chains of carbon atoms with rings that are not aromatic

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4
Q

benzene

A

arene
colourless liquid boiling point of 80 *c
C6H6
carcinogenic
more stable than expected
resonance hybrid

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5
Q

hydrogenation of benzene

A

heat under pressure with a nickel catalyst
C6H6 + 3H2 –> C6H12
can form cyclohexane

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6
Q

bromination of benzene

A

bromine
headed under reflux with a catalyst ( a halogen carrier)

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7
Q

nitration of benzene

A

conc nitric and conc sulfuric acid
warm but not over 50*

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8
Q

friedel crafts alkylation

A

adding an alkyl group
product is methylbenzene (toluene)
aluminum chloride and Lewis acid catalyst
if lewis acid need anhydrous conditions

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9
Q

problems with kekule structure

A

1- should decolourise bromine water as has c-c double bond however it does not
2- should be 4 isomers however only 3 are known to exist
3-bond lenths should not all be the same
4- lower enthlapy change than expected

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10
Q

freidel - crafts alkylation with chloromethane

A

products are an alkylbenzene methylbenzene and hydrogen chloride

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11
Q

freidel - crafts acylation

A

products are keytone phenylethanone and hydrogen chloride

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12
Q

mechanism for bromination

A
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13
Q

mechanism for nitration

A
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14
Q

mechanism for Alkylation

A
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15
Q

mechanism for Acylation

A
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16
Q

bromination of phenol

A

room temp no catalyst
bromine water discolored
white precipitate formed

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17
Q

why does brominination happen more readily in phenols than benzene

A

in Phenol
Benzene requires catalyst of FeBr3
oxygen in OH group has a lone pair which can merge with the electrons in delocalised pi bond
electron density of ring is increased molecule is now more reactive towards electrophiles
bromine polarised as they approach
this breaks Br - Br bond
Br+ electrophile attacks the ring

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18
Q

chiral

A

when a carbon centre is attached to 4 different groups so the mirror image cannot be superimposed onto itself

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19
Q

enantiomer
lactic acid - CH3CH(OH)COOH

A

optical isomers if it has a chiral centre

20
Q

SN1

A

substitution
nucleophilic
unimolecular - 1 species in rds
can attack from either side so two enantiomers can be formed
product has no optical activity
generally tertiary halogenoalkanes
racemic mixture formed

21
Q

SN2

A

substitution
nucleophilic
can only attack from one side
bimolecular- 2 species in rds
arrangement inverted -inversion
so optical activity of product different
generally primary halogenoalkanes
only 1 enantomer formed

22
Q

nucleophilic addition to carbonyls mechanism

A
23
Q

carbonyl reaction with hydrogen cynanide

A

hydrogen attaches to oxygen atom of carbonyl group and a cyanide group attaching to the carbon atom of the carbonyl
planar compound so forms a racemic mixture ie no optical activity.

24
Q

condensation polymerisation

A

joining of two monemers with the elimination of a small molecule

25
Q

polyesters

A

polymers that have monomers bonded with an ester link

26
Q

polarimetry

A

use of a polarimeter to measure optical activity
light passes through a polariser which converts unpolarised to polarised.
then through sample tube containing substance.
if optically activated plane will be rotated. analyser is rotated

27
Q

monochramatic light source

A

light of one colour or frequency

28
Q

racemic mixture

A

a mixture containing equal amounts of two enantiomers
carbonation in triagonal planar around central carbon so equal prob of attack by nucleophile from each side

29
Q

properties of chains

A

increase chain length
- increase boil temp
- decrease solublility

30
Q

carboxylic acids reactions

A

reduction - to primary alchohols
neutralisation - completely with aqueous alkali forms carboxylate salts
halogenation - OH is replaced by halogen forms aceyl halogenides
esterfacation- alcohol and acid catalyst forms ester

31
Q

acyl chlorides

A

RCOCl
contain carbonyl group
replaced the oh in cooh with cl

32
Q

acyl reaction with water

A

vigorous reaction
form carboxylic acid and HCl gas

33
Q

acyl reaction with alcohols

A

form Esther and HCl gas

34
Q

acyl reaction with conc ammonia

A

ammonium chloride and HCl formed

35
Q

acyl reaction amines

A

substitued amide e.g N-substitued amide and HCl
secondary amine form two alkyl groups

36
Q

esters

A

naming -
-thyl -oate
RCOOR
double bonded O
colourless liquids
low melting and boiling
insoluble in water
smells of fruit

37
Q

hydrolysis of esters

A

opposite of esterification
acidic- acid speed up as a catalyst
alkaline - goes onto completion rather than equilibrium
-produces carboxylate salt

38
Q

test for aldehydes and keytones

A

oxidation with fehlings , benedicts or tollens
positive result aldehyde
negative keytone
fehlings + benedicts - blue > red
tollens - colourless > silver

39
Q

esther and acyl chloride reactivity

A

acyl chlorides more reactive
as more suseptable to attack from nucleophiles

40
Q

differences in esterfacation with oyl and carboxylic acid

A

irreversable - reversable
HCl formed - H2O formed
faster
no acid catalyst needed - needed

41
Q

cyclicalcohol to cyclicalkene

A

elimination experiement
phosphoric acid
heat
use distilation and seperating funell
then dry

42
Q

amyl acetate

A

pentyl ethanoate

42
Q

formation of isoamyl acetate

A

3-methylbutan-1-ol

42
Q

hydrolsis of amyl acetate
compare

A

2 methods
aqeous acid or alkali
s - both make same alcohol
d
-acid is reversible alkaline is irriversable
-acid produce carboxylic acid alkaline produce carboxylate ion
-acid catalyst alkaline reactant

43
Q

how can samples of enatiomers be distinguished

A

rotate plane polarised light in different directions

44
Q

no of optical isomers

A

number of chiral centres x2

45
Q

iodoform test

A

CH3CO feature
react with I2 OH- to form a yellow precipitate
triiodomethane - CHI3

chemistry (25 decks)

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