ORGANIC CHEMISTRY #I
BENZENE
U ACTUALLY
MAKING ALIPHATIC AMINES
-
same bond length
↳ - - - - - - -
J he at V R R
6 S
Kenule's shichrt · I shows delocanised * naloalone
? R - N- · - -in
system emos
-
2 ~
H
↓ -
-
alternating double/single
reactive
bond
Excess
anmania
U -R
n
X wrong ---are delocalised + heat
↑ Orbital forms a dclocanised
ring of e- * doesn't decolonise bromine war ess
nalamone
e .
. 2CKzNUz
g +
CUy(H2Cl
emonol
Danmonid
BENZENE STABILITY
-H-c
MDURE : primary avines pair
i
in
1 - lone e-
compared enthalpy
acts as a mcleophile
COMBUSTION OF BENZENE ↳ react with renaming halogeromones
change of hydrogenation UzN :
J
Secondary
=
benzene
=
tertiary salts
in and cyclohexa-1 3 5-triene
1502 6H20
,
2CHo + >
12CO2 smoky
-
,
+ black =
quartenay
flame
complete combustion OR
N
cyclonexene benzene unreached
CATALYTIC HYDROGENATION M
#Y EY
carban
realistically incomplete combustion >
- +
(15)
reduce nitriles >
->
primary anives
PURE :
nickle caracyst
(or Pt)
W
R-CH2- CN +
212 -
> R- CH2-CHzNU2
Neup
THEORETICAL -
120 usmoi -
360 u/mol- ↑ pressure
dissolved in
non-aqueous
EXPERIMENTAL
-h)
208 moli] everya
Move ARENES R-CH2
Steg-C-CUN
see _
SE
Br
[
than 12 Pt/Ni catalyst
I
ADDITION OF BROMINE to amenes
colourless ! AMINES AND COMPLEX IONS
M on NUz
·
f
Y
U I
TOP Tamine
-
-
c
Ia
Br C Br OHz
- -
-
H
i' H20.. ↓
-
a
: Br
-
>
-
[colonicIn20u] +
more ! ->
H20 -
pale blue ppt.
-
ELECTROPHILIC SUBSTITUTION copper(II) sulfate
high e-density attracts electrophiles
↳ too stable for electrophilic addition
! to add on to me
AMINES AND ACYLCHLORIDES
benzene ring must
e-are attacked substituted for N
delocated C-H +live
-
II is
to me carbocation
c - in have
very strong
t more to neurraise -
R H livering
change groups
+
[
+
U
n-c-cannca
-
not the enough
Ht ! halogen
use a carrier
↳ AlCB ! i utylamine
-
> butylammonium chloride
([KaNUs] ci
+
his substituted +
2e
moveto
date
a
ChsCOll + 2GUaNUe-
> CUsCONNCula +
[CxUaNUg] C1
↑
AMINES AND ACIDS
PlIENOLS
-
CHaNH2 + HClS CuHqNUz
+
Cl
amine + acid Salt /no water
NITRATION OF BENZENE C+
HqNU2 + U20 >
- CYqNUg
+
+ On-
-
more reactive
-electrophilic
than benzene (e density
substitution reactions
-
are more
/ orbital
on group
likely
overlap
to occur conditions
55
°
C
:
1 substitution
↳ explosives
Layes
small
anines
+ water
alkane sortia
-
b
=
+
reflux ! H +
NHz
+
CH , 200
>
-
NH g C , COOH
-
catalyst
Overa +
↑So =
Multiple substitutions
lose
with the
pair overlaps
delocalised e-
UNO3 +
12SO4
-Not + 1504- OH + NH3 + CH2C00
- -
> NHzCH2COO
-
+ H20
decanoes
a
&
↳ partially delocorised into
H
the pi-system M"
120 NHz
+ +
COO NUs CHICO Ou
-
+
+ Ch , >
-
AMD
·
- H
carboya
as
NUs" CH2C00 NHCH2COO no
-
>
-
On +
↳ reacts with 2
USO4-
-
--
BROMINATIO M nimonium ic uU
-d
O
BHB
>
-
i in
-
u
water I
R
orange ppt.
- Whitep Anophenol HALOGENATION OF BENZENE N-substituted anide
↳ smells of antiseptic
↳ insoluble
of
NITRATION MAKING AMIDES
o
"We
↑ white
mishs
sures
+
-reduces e-ousity M
U O
e .
.
g
Br +
Febr >
-
Brt +
FeBry WRITE LIVE :
Nhn-c + HCl (g)
+ Brea
conditions :
rtp ! ↓ ammonia i Wrz
Nz ethanoyl
AMINO ACIDS
chloride ethanamide
& Bu
FRIEDEL-CRAFTS REACTIONS
white is
mis,
600C 3
HO-c-c
reflux U O ↑
I
1
anhydrous + CHN12- - n -C -
+ HCl (g)
primary n urchs
carbony =
carboxylic aci
ACYLCHLORIDE IRCO-) BENZENE
amine
+ N-methy emaanide carbonz = animo
>
-
benzene becomes weaker 2-amino propanoic acid
↳ easier to modify
↳ useful products
R -
+
C
Al - R
C
o - THIN LAYER CHROMATOGRAPHY
GRIGNARD REAGENTS
-
CHROMATOGRAM
-
a ↳ organomagnesium compound
*sourt
any
D
⑧
0 Catalyst
reformed
halogenoalkane + magnesium
I
O ① dry eth
> move once the
i
-
t
R-MgBr-
② dilute
#C
less stable
(protonates
d
aldehydes/ +
grigandsa
]
travelled netones
distance by spot
diffent sombility emobilepeaeas
in
Rf =
distance travelled by solvent
fixed for each chemical
HALOGENOALKANES /C-CHALKYL) + BENZENE
factors :
- tempera
a
TLC plate
-
make up of
>
-
benzene becomes weaker
C) ↳ easier to modify
-Al SEPARATION
·
+
Al(4
-
↳ NOTES ON
>
-
R +
useful products
↳ remove impurities
ASPIRIN
dissolved in wa
L
S
/2
CI (
- al fo See
-
aqueous layer containing
~ water-soluble impurities
Catalyst REACTANTS AND PRODUCTS
↳
R a reformed impure product
↳ arain off
OH
nx-
x
salicylica aspirit etonoic
ethanoic acid
anhydride
↳ used instead : safer-doesn't produce Hl gas
of emanoyl less corrosive
O Al [13 chloride
# 0 AlC3-
PURITY AND MELTING/BOLLING
1 C + C Catalyst POINTS
,
& reformed
BENZENE
U ACTUALLY
MAKING ALIPHATIC AMINES
-
same bond length
↳ - - - - - - -
J he at V R R
6 S
Kenule's shichrt · I shows delocanised * naloalone
? R - N- · - -in
system emos
-
2 ~
H
↓ -
-
alternating double/single
reactive
bond
Excess
anmania
U -R
n
X wrong ---are delocalised + heat
↑ Orbital forms a dclocanised
ring of e- * doesn't decolonise bromine war ess
nalamone
e .
. 2CKzNUz
g +
CUy(H2Cl
emonol
Danmonid
BENZENE STABILITY
-H-c
MDURE : primary avines pair
i
in
1 - lone e-
compared enthalpy
acts as a mcleophile
COMBUSTION OF BENZENE ↳ react with renaming halogeromones
change of hydrogenation UzN :
J
Secondary
=
benzene
=
tertiary salts
in and cyclohexa-1 3 5-triene
1502 6H20
,
2CHo + >
12CO2 smoky
-
,
+ black =
quartenay
flame
complete combustion OR
N
cyclonexene benzene unreached
CATALYTIC HYDROGENATION M
#Y EY
carban
realistically incomplete combustion >
- +
(15)
reduce nitriles >
->
primary anives
PURE :
nickle caracyst
(or Pt)
W
R-CH2- CN +
212 -
> R- CH2-CHzNU2
Neup
THEORETICAL -
120 usmoi -
360 u/mol- ↑ pressure
dissolved in
non-aqueous
EXPERIMENTAL
-h)
208 moli] everya
Move ARENES R-CH2
Steg-C-CUN
see _
SE
Br
[
than 12 Pt/Ni catalyst
I
ADDITION OF BROMINE to amenes
colourless ! AMINES AND COMPLEX IONS
M on NUz
·
f
Y
U I
TOP Tamine
-
-
c
Ia
Br C Br OHz
- -
-
H
i' H20.. ↓
-
a
: Br
-
>
-
[colonicIn20u] +
more ! ->
H20 -
pale blue ppt.
-
ELECTROPHILIC SUBSTITUTION copper(II) sulfate
high e-density attracts electrophiles
↳ too stable for electrophilic addition
! to add on to me
AMINES AND ACYLCHLORIDES
benzene ring must
e-are attacked substituted for N
delocated C-H +live
-
II is
to me carbocation
c - in have
very strong
t more to neurraise -
R H livering
change groups
+
[
+
U
n-c-cannca
-
not the enough
Ht ! halogen
use a carrier
↳ AlCB ! i utylamine
-
> butylammonium chloride
([KaNUs] ci
+
his substituted +
2e
moveto
date
a
ChsCOll + 2GUaNUe-
> CUsCONNCula +
[CxUaNUg] C1
↑
AMINES AND ACIDS
PlIENOLS
-
CHaNH2 + HClS CuHqNUz
+
Cl
amine + acid Salt /no water
NITRATION OF BENZENE C+
HqNU2 + U20 >
- CYqNUg
+
+ On-
-
more reactive
-electrophilic
than benzene (e density
substitution reactions
-
are more
/ orbital
on group
likely
overlap
to occur conditions
55
°
C
:
1 substitution
↳ explosives
Layes
small
anines
+ water
alkane sortia
-
b
=
+
reflux ! H +
NHz
+
CH , 200
>
-
NH g C , COOH
-
catalyst
Overa +
↑So =
Multiple substitutions
lose
with the
pair overlaps
delocalised e-
UNO3 +
12SO4
-Not + 1504- OH + NH3 + CH2C00
- -
> NHzCH2COO
-
+ H20
decanoes
a
&
↳ partially delocorised into
H
the pi-system M"
120 NHz
+ +
COO NUs CHICO Ou
-
+
+ Ch , >
-
AMD
·
- H
carboya
as
NUs" CH2C00 NHCH2COO no
-
>
-
On +
↳ reacts with 2
USO4-
-
--
BROMINATIO M nimonium ic uU
-d
O
BHB
>
-
i in
-
u
water I
R
orange ppt.
- Whitep Anophenol HALOGENATION OF BENZENE N-substituted anide
↳ smells of antiseptic
↳ insoluble
of
NITRATION MAKING AMIDES
o
"We
↑ white
mishs
sures
+
-reduces e-ousity M
U O
e .
.
g
Br +
Febr >
-
Brt +
FeBry WRITE LIVE :
Nhn-c + HCl (g)
+ Brea
conditions :
rtp ! ↓ ammonia i Wrz
Nz ethanoyl
AMINO ACIDS
chloride ethanamide
& Bu
FRIEDEL-CRAFTS REACTIONS
white is
mis,
600C 3
HO-c-c
reflux U O ↑
I
1
anhydrous + CHN12- - n -C -
+ HCl (g)
primary n urchs
carbony =
carboxylic aci
ACYLCHLORIDE IRCO-) BENZENE
amine
+ N-methy emaanide carbonz = animo
>
-
benzene becomes weaker 2-amino propanoic acid
↳ easier to modify
↳ useful products
R -
+
C
Al - R
C
o - THIN LAYER CHROMATOGRAPHY
GRIGNARD REAGENTS
-
CHROMATOGRAM
-
a ↳ organomagnesium compound
*sourt
any
D
⑧
0 Catalyst
reformed
halogenoalkane + magnesium
I
O ① dry eth
> move once the
i
-
t
R-MgBr-
② dilute
#C
less stable
(protonates
d
aldehydes/ +
grigandsa
]
travelled netones
distance by spot
diffent sombility emobilepeaeas
in
Rf =
distance travelled by solvent
fixed for each chemical
HALOGENOALKANES /C-CHALKYL) + BENZENE
factors :
- tempera
a
TLC plate
-
make up of
>
-
benzene becomes weaker
C) ↳ easier to modify
-Al SEPARATION
·
+
Al(4
-
↳ NOTES ON
>
-
R +
useful products
↳ remove impurities
ASPIRIN
dissolved in wa
L
S
/2
CI (
- al fo See
-
aqueous layer containing
~ water-soluble impurities
Catalyst REACTANTS AND PRODUCTS
↳
R a reformed impure product
↳ arain off
OH
nx-
x
salicylica aspirit etonoic
ethanoic acid
anhydride
↳ used instead : safer-doesn't produce Hl gas
of emanoyl less corrosive
O Al [13 chloride
# 0 AlC3-
PURITY AND MELTING/BOLLING
1 C + C Catalyst POINTS
,
& reformed
