Chemistry Unit 2 Revision Notes

Enthalpy
Enthalpy (H) is a type of potential energy (heat).
Breaking bonds re!ires energy and is an endothermi" rea"tion.
#aking bonds releases energy and is an e$othermi" rea"tion.
Endothermi" % positive enthalpy "hange
E$othermi" % negative enthalpy "hange
&n an e$othermi" rea"tion' heat is released. (his leaves the prod!"ts of the rea"tion )ith less
potential energy than the rea"tants.
ΔH % H
*R+,UC(-
. H
RE/C(/N(-
ΔH
O
: (he enthalpy "hange for a rea"tion' !nder standard "onditions' )ith all s!bstan"es in
their standard states. Conditions0 ( % 2123' * % 4553*a' Con"entration % 4mol6dm
7
-pe"ifi" Heat Capa"ity
(he spe"ifi" heat "apa"ity of any s!bstan"e is the amo!nt of heat energy re!ired to raise the
temperat!re of 4g of s!bstan"e by 43.
% m"Δ(
% energy given o!t (8) m % mass (g) " % spe"ifi" heat "apa"ity (8g
94
3
94
)
Δ( % "hange in temperat!re (3) :.42 % spe"ifi" heat "apa"ity of )ater
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Enthalpy (H)
Rea"tants
*rod!"ts
(his diagram sho)s the enthalpy of the rea"tants and
prod!"ts of a rea"tion. &t sho)s that the prod!"ts of the
rea"tion have a lo)er enthalpy (and are therefore more
stable) than the rea"tants and so the rea"tion is
e$othermi".
-tandard Enthalpy of ;ormation
ΔH
f
O
: (he enthalpy "hange for the formation of one mole of a "ompo!nd from its elements'
!nder standard "onditions )ith all s!bstan"es being in their standard states.
<hat is the importan"e of kno)ing the standard enthalpy of formation=
• &t tells yo! the stability of a "ompo!nd relative to its elements (negative val!e means
more stable)
• &f ΔH
f
O
is kno)n for all s!bstan"es in an e!ation' ΔH for the rea"tion "an be
"al"!lated.
-tandard Enthalpy of Comb!stion
ΔH
"
O

: (he enthalpy "hange for the "omplete "omb!stion in o$ygen of one mole of a
"ompo!nd !nder standard "onditions' )ith all s!bstan"es being in their standard states.
#aking and Breaking Bonds
(he mean bond enthalpy is the amo!nt of heat energy either re!ired to break or given o!t
from making a bond' averaged over different environments of that bond.
#aking bonds % e$othermi"
Breaking bonds % endothermi"
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Hess's Law
Hess>s la) states that the enthalpy "hange of a rea"tion depends only on the initial and final
states of the rea"tion and is independent of the ro!te by )hi"h the rea"tion may o""!r.
ΔH
/
% ΔH
B
? ΔH
C
Hess> la) only deals )ith heat energy.
;irst @a) of (hermodynami"s
Energy "an neither be "reated or destroyed b!t it "an be "onverted from one form in to
another.
/lso kno)n as >(he *rin"iple of Conservation of Energy>.
Hess>s @a) and Δ H
"
O

2C ? 7H
2
→ C
2
H
A
Comb!stion of individ!al rea"tants and prod!"ts from rea"tion above0 2C ? 2+
2
→ 2C+
2
7H
2
?
3
2
+
2
→ 7H
2
+ C
2
H
A
?
7
2
+
2
→ 2C+
2
? 7H
2
+
Ba"k to original e!ation0
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2C ? 7H
2

C
2
H
6
C+
2
? 7H
2
+
2BΔH
"
Ө
(C)C
7BΔH
"
Ө
(H
2
)C 7BΔH
"
Ө
(H
2
)C 9BΔH
"
Ө
(C
2
H
A
)C
Hess>s @a) and Δ H
f
O

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CH
:
? 2+
2

C+
2
? 2H
2
+
C ? 2H
2
? 2+
2

92BΔH
f
Ө
(+
2
)C
9BΔH
f
Ө
(CH
:
)C
ΔH
f
Ө
(C+
2
)
92BΔH
f
Ө
(+
2
)C
Kinetics
Collision (heory
<hen a "hemi"al rea"tion takes pla"e' the rea"tant parti"les m!st "ollide.
No rea"tion )ill o""!r if0
• 2 identi"al mole"!les "ollide
• #ole"!les "ollide too slo)ly
• (he "ollision o""!rs at the )rong angle
(here are 2 definitions for the rate of rea"tion0
4) -peed rea"tants are !sed !p i.e.
2) -peed prod!"ts are formed i.e.
Brea"tantC % "on"entration of rea"tant
Bprod!"tC % "on"entration of prod!"t
Unit % moldm
97
s
94
<hen all rea"tants are !sed !p' Brea"tantC % 5 so rate of rea"tion (R+R) % 5
/"tivation Energy
(he minim!m energy re!ired to start a rea"tion.
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Δ[reactant]
time
Δ[product]
time
Enthalpy (H)
Rea"tants
*rod!"ts
E
a
(his diagram sho)s the a"tivation energy of an
e$othermi" rea"tion.
Rate Draph
(he p!rple line has half the moles of the red line and so it levels off at a smaller vol!me (half
the vol!me of the red line).
(he green line has the same n!mber of moles as the red line' so levels off at the same
vol!me of prod!"t. Ho)ever' the green line has do!ble the "on"entration of the red line and so
it is steeper.
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Enthalpy (H)
Rea"tants
*rod!"ts
E
a
(his diagram sho)s the a"tivation energy of an
endothermi" rea"tion.
E
o
l
!
m
e

o
f

p
r
o
d
!
"
t
time
Red line % F5"m
7
4# HCl
*!rple line % F5"m
7
5.F# HCl
Dreen line % 2F"m
7
2# HCl
#a$)ell9BoltGmann ,istrib!tion
E
a
% a"tivation energy
/rea bet)een "!rve and $ a$is to the right of E
a
% n!mber of parti"les that have eno!gh
energy to rea"t )hen they "ollide.
*ink line % even higher temperat!re
/"tivation energy (E
a
) !naffe"ted by temperat!re.
Higher temperat!re means the Emp is larger.
/t a higher temperat!re' there are the same n!mber of parti"les in a given vol!me. *arti"les
have more energy so they move faster. (his means there are more "ollisions and therefore
more s!""essf!l "ollisions' so rate of rea"tion in"reases.
))).mattsrevision."om
Energy E
a
N
o

o
f

p
a
r
t
i
"
l
e
s
Emp
(his sho)s the distrib!tion of energy for parti"les in a
rea"tion.
Emp % most probably energy
(he area !nder the graph is e!al to the n!mber of
parti"les.
Energy E
a
N
o

o
f

p
a
r
t
i
"
l
e
s
(he diagram sho)s the effe"t of temperat!re on the
distrib!tion of parti"le energies.
(he area !nder ea"h "!rve is the same as it
represents the total n!mber of parti"les.
Bl!e line % original temperat!re
Red line % higher temperat!re
(he area !nder the red "!rve is smaller than the area !nder the bl!e "!rve so there are fe)er
parti"les in the red sol!tion.
(he Emp does not "hange as temperat!re does not "hange.
/t a higher "on"entration' there are more parti"les in a given vol!me and so there are more
"ollisions. (his means there )ill be more s!""essf!l "ollisions. *arti"les have the same energy
as before the "hange in "on"entration and so rate of rea"tion in"reases.
Catalysts
Catalysts provide an alternative >ro!te> for a rea"tion' )ith a lo)er a"tivation energy. Catalysts
are not !sed !p in a rea"tion.
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Energy E
a
N
o

o
f

p
a
r
t
i
"
l
e
s
(his diagram sho)s the effe"t of "on"entration on the
distrib!tion of parti"le energies.
Bl!e line % original "on"entration
Red line % lo)er "on"entration
Enthalpy (H)
Rea"tants
*rod!"ts
(he diagram sho)s "!rves for 2 separate rea"tionsH
one )ith a "atalyst (sho)n by the bl!e line) and one
)itho!t a "atalyst (sho)n by the green line).
(he rea"tion )ith a "atalyst has a lo)er a"tivation
energy than the rea"tion )itho!t a "atalyst.
(he enthalpy "hange for both rea"tions is the same.
/ heterogeneo!s "atalyst is a "atalyst that is in a different phase to the rea"tants e.g. a solid
ni"kel "atalyst for the rea"tion bet)een hydrogen gas and alkene gas.
/ homogeneo!s "atalyst is a "atalyst that is in the same phase as the rea"tants e.g. "hlorine
gas "atalysing the depletion of oGone gas.
/s the "atalyst lo)ers a"tivation energy' "osts of prod!"tion de"rease as less energy is
needed. (his also means fe)er non9rene)able so!r"es of energy are !sed.
(he !se of a "atalyst also means prod!"ts are made more !i"kly.
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Energy
E
a
N
o

o
f

p
a
r
t
i
"
l
e
s
E
a
"atalyst
(his diagram sho)s the effe"t of !sing a
"atalyst on a"tivation energy.
Equilibria
/ dynami" e!ilibri!m is one in )hi"h the for)ard and ba"k)ard rea"tions happen at the same
rate.
Con"entrations of rea"tants and prod!"ts remain "onstant' b!t the "on"entration of the
rea"tants does not have to be e!al to the "on"entration of prod!"ts.
<hen in e!ilibri!m' the e$tent of a rea"tion is kno)n as the position of e!ilibri!m e.g. if
there is a larger "on"entration of prod!"ts than rea"tants' )e say the e!ilibri!m lies to the
right.
@e Chatelier>s *rin"iple
/ system at e!ilibri!m )ill rea"t to oppose any "hange imposed !pon it.
Con"entration
-!ppose the "on"entration of rea"tants in"reases.
(hen the system )ill move to the right to oppose the "hange (a""ording to @e Chatelier) and
so the amo!nt of prod!"ts )ill in"rease.
*ress!re
+nly involves gas mole"!les.
/n in"rease in total press!re shifts the position of e!ilibri!m to the side )ith fe)er gas
mole"!les.
))).mattsrevision."om
E.g.
N
2
(g) ? 7H
2
(g) 2NH
7
(g)
N!mber of gas mole"!les0 4 ? 7 2
% : 2
-o an in"rease in press!re )o!ld "a!se an in"rease in the yield of NH
7
as the system moves
to the side of lo)er press!re and so moves to the right hand side.
(he Haber *ro"ess
N
2
(g) ? 7H
2
(g) 2NH
7
(g)
*rod!"es ammonia )hi"h is !sed for fertiliser.
Conditions0 255 atmospheres' :F5
o
C' iron "atalyst
Higher temperat!re % lo)er yield as for)ard rea"tion is e$othermi".
@o)er temperat!re % higher yield b!t slo) rate of rea"tion.
Higher press!re % high "osts
@o)er press!re % lo)er yield
))).mattsrevision."om
Redox
,efinitions of +$idation
4) /ddition of o$ygen
2) @oss of hydrogen
7) @oss of ele"trons
:) &n"rease in o$idation n!mber
F) ,e"rease in ele"tron density
+$idation -tates
(he n!mber of ele"trons a spe"ies needs to gain or lose to make a ne!tral atom.
E.g. ;e
5
(as atoms by themselves have an o$idation state of 5)' ;e
2
?7
+
7
92
' ;e
?2
+
92
R!les for +$idation -tate
4) Dro!p 4 is al)ays ?4
2) Dro!p 2 is al)ays ?2
7) Charge on ion is !s!ally the same as the o$idation state
:) Hydrogen is al)ays ?69 4
F) ;l!orine is al)ays 94 as it is the most ele"tronegative element
A) +$ygen is !s!ally 92
I) / gro!p I element is 94 if it is more ele"tronegative than the other s!bstan"e
E.g. Cl
2
?4
+
92
(as o$ygen is more ele"tronegative than "hlorine)' H
2
+
2
' Cl
?7
;
7
94
))).mattsrevision."om
Red!"tion is the gaining of ele"trons
/n o$idising agent is an ele"tron a""eptor (it gets red!"ed).
/ red!"ing agent is an ele"tron donor (it gets o$idised).
R!les for Balan"ing Half E!ations
4) +nly one element in ea"h half e!ation sho!ld "hange its o$idation state.
2) (he half e!ation m!st balan"e for atoms.
7) (he half e!ation m!st balan"e for "harges.
:) (he f!ll e!ation m!st balan"e for atoms and "harges.
F) H
?
' +H
9
and H
2
+ are often added to half e!ation to balan"e atoms.
))).mattsrevision."om
Group 7
,iatomi" atoms' kno)n as halogens' )hi"h form ins "alled halides.
;l!orine is a pale yello) diatomi" gas.
Chlorine is a green diatomi" gas.
Bromine is a bro)n diatomi" li!id.
&odine is a grey diatomi" solid.
Boiling *oint0 &n"reases do)n the gro!p. (his is be"a!se the in"reased siGe of the mole"!les
"a!ses in"reased Ean der <aals for"es bet)een the mole"!les and so more energy is needed
to break the intermole"!lar for"es.
Ele"troni" Config!ration0 Highest energy ele"trons in p s!b9shell. (hey are the most rea"tive
non9metals. (hey are strong o$idising agents (god at gaining ele"trons).
/tomi" Radi!s0 &n"reases do)n the gro!p. Higher atomi" n!mber % more ele"trons. (he
ele"trons fill shells f!rther and f!rther from the n!"le!s.
&oni" Radi!s0 &n"reases do)n the gro!p. &ons are larger than their "orresponding atom in gro!p
I as the e$tra ele"tron repels the others so radi!s in"reases.
Ele"tronegativity0 ,e"reases do)n the gro!p. N!"lear "harge in"reases' ho)ever there are
more shells and more shielding so less p!ll on ele"trons. (here is a larger atomi" radi!s so
less p!ll on o!ter ele"trons.
+$idising po)er0 <eaker do)n the gro!p. (his is for the same reasons as ele"tronegativity.
))).mattsrevision."om
,ispla"ement Rea"tions
/ rea"tion in )hi"h a more rea"tive element repla"es a less rea"tive element from an a!eo!s
sol!tion of the latter>s ions.
/ more rea"tive halogen )ill displa"e a less rea"tive one. Halides are salts formed from
halogens.
,ispla"ement of halides0 3Cl )ith bromine % no "hange as bromine doesn>t displa"e "hlorine.
3Cl )ith iodine % no "hange.
*re"ipitation Rea"tion
(he formation of a solid from a sol!tion d!ring a "hemi"al rea"tion.
,isproportionation Rea"tion
(he o$idation and red!"tion of the same element in a redo$ rea"tion.
E.g. Cl
2
5
(g) ? H
2
+ (l) HCl
94
(a) ? H+Cl
?4
(a)
))).mattsrevision."om
(esting for Halide &ons
(here is no pre"ipitate for fl!oride
Halide Colo!r of *re"ipitate -ol!bility
Chloride <hite solid -ol!ble in )eak ammonia
Bromide Cream solid &nsol!ble in )eak ammonia'
sol!ble in "on"entrated
ammonia
&odide Jello) solid &nsol!ble in )eak and
"on"entrated ammonia
Rea"tion0 3K (a) ? /gN+
7
(a) → 3N+
7
(a) ? /gK (s)
Halogen % o$idising agent
Halide % red!"ing agent
Rea"tions )ith -!lf!ri" /"id
;l!oride0 Na; ? H
2
-+
:
→ NaH-+
:
? H;
H
2
-+
:
is a proton donor
Not a redo$ rea"tion as ;
9
is not very good at red!"ing.
Chloride0 NaCl ? H
2
-+
:
→ NaH-+
:
? HCl
Not a redo$ rea"tion as "hlorine is a bad red!"ing agent.
))).mattsrevision."om
Bromide0 NaBr ? H
2
-+
:
→ NaH-+
:
? HBr
HBr rea"ts f!rther as it is a good red!"ing agent0
2HBr ? H
2
-+
:
→ Br
2
? -+
2
? 2H
2
+
HBr % )hite misty f!mes
Br
2
% red6bro)n f!mes
&odide0 Na& ? H
2
-+
:
→ NaH-+
:
? H&
2H& ? H
2
-+
:
→ :&
2
? H
2
- ? :H
2
+
&
2
% bla"k solid
H
2
- % bad eggs smell
H& % steamy f!mes
&odide is the best red!"ing agent' fl!oride is the )orst.
Rea"tion of Chlorine )ith Cold' ,il!te' /!eo!s -odi!m Hydro$ide and <ater
Cl
2
? H
2
+ HCl ? H"l+
Cl
2
? 2Na+H → NaCl ? NaCl+ ? H
2
+
NaCl and NaCl+ are !sed as a blea"h.
))).mattsrevision."om
Group 2
/lkaline earth metals is their other name. &n the LsM blo"k. ;orm basi" o$ides.
/tomi" Radi!s0 &n"reases do)n the gro!p. (here is a ne) shell for ea"h atom as yo! go do)n
the gro!p so an in"rease in shielding so ele"trons are f!rther a)ay from the n!"le!s. /ltho!gh
n!"lear "harge also in"reases' atomi" radi!s still in"reases.
&oni" Radi!s0 &n"reases do)n the gro!p for the same reasons as atomi" radi!s. Ho)ever' ioni"
radi!s is smaller than "orresponding atomi" radi!s as an ele"tron is lost so the o!termost
ele"tron is no) "loser to the n!"le!s. (here is also less shielding if a 2
?
ion is formed.
#elting *oint0 ,e"reases do)n the gro!p. -!rfa"e "harge density de"reasesH every atom
"ontrib!tes 2 ele"trons' b!t the siGe of the ion in"reases so metalli" bonding gets )eaker. /
larger ion has less binding from its ele"tron "lo!d. #agnesi!m does not fit this trend as it has a
"rystalline str!"t!re )hi"h affe"ts melting point.
;irst &onisation Energy0 ,e"reases do)n the gro!p. /tomi" radi!s in"reases' shielding
in"reases. -e"ond ionisation energy greater than first as there is an !npaired ele"tron so
stronger attra"tion to the n!"le!s. (hird ionisation energy signifi"antly greater than se"ond as
there is one less shell so less shielding and smaller ioni" radi!s.
Rea"tivity )ith <ater0 Rea"tivity in"reases do)n the gro!p.
#g (s) ? 2H
2
+ (l) → #g(+H)
2
(a) ? H
2
(g)
-ol!bility of Hydro$ides0 -ol!bility in"reases do)n the gro!p. #etal ions are larger so s!rfa"e
"harge density de"reases. @o)er attra"tion bet)een +H
9
and 2
?
ions so ions split a)ay more
easily so greater "on"entration of +H
9
ions (as they are by themselves).
-ol!bility of -!lfates0 -ol!bility in"reases do)n the gro!p. 2
?
ion gets larger so has lo)er
s!rfa"e "harge density so less attra"ted to the polar )ater mole"!le.
))).mattsrevision."om
Use of #g(+H)
2
is milk of magnesia )hi"h ne!tralises stoma"h a"id.
#g(+H)
2
(s) ? 2HCl (a) → #gCl
2
(a) ? 2H
2
+ (l)
Use of Ca(+H)
2
is for )hen farmers >lime> fields to "ontrol soil a"idity.
Use of Ba-+
:
is that it is opa!e to $9rays so "an be !sed to $9ray the digestive system.
BaCl
2
is !sed to dete"t s!lfate ions as a )hite pre"ipitate forms )hen BaCl
2
is added to a
sol!tion "ontaining s!lfite ions.
))).mattsrevision."om
Extraction of Metals
(here are three )ays to e$tra"t a metal0
4) Use of a more rea"tive "ompo!nd
2) Ele"trolysis
7) +""!r as a native metal
Red!"tion0 (he removal of o$ygen from a "ompo!nd.
/ metal "ompo!nd is !s!ally an o$ide or a s!lphide. Roasting t!rns an o$ide in to a s!lphide.
+ne al!mini!m ore is ba!$ite % /l
2
+
7
% al!mini!m o$ide
+ne iron ore is haematite % ;e
2
+
7
% iron o$ide
-!lfides
Converted in to o$ides by roasting. Ho)ever this prod!"es s!lf!r dio$ide )hi"h "a!ses a"id
rain. (he s!lf!r dio$ide (-+
2
) prod!"ed is "ontained and !sed to make s!lf!ri" a"id by the
contact process Uses in"l!de fertilisers' e$plosives' medi"ines and plasti"s.
-tep 40 -+
2
is o$idised by a vanadi!m (E) . o$idation state % F . "atalyst.
2-+
2
(g) ? +
2
(g) 2-+
7
(g)
-tep 20 -+
7
(s!lf!r trio$ide) is !sed to make s!lf!ri" a"id0
-+
7
? H
2
+ → H
2
-+
:
(he pro"ess of metal e$tra"tion depends on the p!rity re!ired' energy re!irements' "ost of
the red!"ing agent and the position of the metal in the rea"tivity series.
))).mattsrevision."om
Eanadi!m
(E)
&ron' #anganese and Copper
Red!"ed by "arbon or "arbon mono$ide.
&ron0 &ron (&&) o$ide ;e
2
+
7
(s) ? 7C+ (g) → 2;e (l) ? 7C+
2
(g)
#anganese0 #anganese (&E) o$ide #n+
2
? C+ → #n+ (s) ? C+
2

Ho)ever' #n+ is not red!"ed eno!gh' so another rea"tion o""!rs #n+ ? C → #n (l) ? C+
Copper0 #ost "ommonly C!
2?
C!+ (s) ? C (s) → C! (l) ? Co (g)
(itani!m
(itani!m (&E) o$ides. (i+
2
is very "ommon.
+$ide "an be red!"ed by "arbon b!t the titani!m prod!"ed rea"ts )ith "arbon to form titani!m
"arbide )hi"h is not good.
E$tra"tion0
(he o$ide is "onverted to "hloride (i+
2
(s) ? 2Cl
2
(s) ? 2C (s) → (iCl
:
(l) ? 2C+ (g)
&t is then red!"ed )ith Na or #g (iCl
:
(l) ? :Na (s) → (i (s) ? :NaCl (s)
(he red!"tion is "arried o!t in an argon atmosphere as the titani!m rea"ts )ith o$ygen at high
temperat!res.
(!ngsten
(!ngsten (E&) o$ide . <+
7
Carbon is not !sed to red!"e t!ngsten as t!ngsten "arbide is a bi9prod!"t )hi"h affe"ts the
properties of t!ngsten. Hydrogen is !sed as a red!"ing agent as it is more rea"tive than
))).mattsrevision."om
t!ngsten. Narro) metal t!bes are !sed' f!rna"e is heated to 2F5
o
C.
<+
7
(s) ? 7H
2
(g) → < (s) ? 7H
2
+ (g) /ny !nrea"ted H
2
is re!sed.
Ho)ever' H
2
is a flammable gas. Jo! "annot tell if hydrogen has leaked as it is "olo!rless and
does not smell. &t also b!rns )ith an invisible flame.
/l!mini!m
Ele"trolysis of p!rified ba!$ite (/l
2
+
7
) dissolved in molten "ryolite (Na
7
/l;
A
). #elting point of
/l
2
+
7
% 2555
o
C )hereas melting point of ba!$ite dissolved in molten "ryolite % 1I5
o
C so less
energy and therefore ele"tri"ity is !sed. Ele"trodes are made of "arbon. C!rrent % 255555/
Rea"tion at "athode0 /l
7?
(l) ? 7e
9
→ /l (l)
Rea"tion at anode0 2+
29
(l) → +
2
(g) ? :e
9
-ome of the +
2
rea"ts )ith the "arbon anodes0
2C (s) ? +
2
(g) → 2C+ (g) at high temperat!res
C (s) ? +
2
(g) → C+
2
(g)
@ots of ele"tri"ity is !sed (as the "ryolite has to be melted and the /l
2
+
7
has to be
de"omposed) so this pro"ess is only e"onomi"al if ele"tri"ity is "heap.
(here is a potential environmental problem as the )aste "ryolite "a!ses fl!oride poll!tion.
))).mattsrevision."om
Haloal!anes
Haloalkanes "ontain a polar "ovalent bond as there are differen"es in ele"tronegativity.
/ n!"leophile is an ele"tron pair donor.
E$amples of n!"leophiles in"l!de NH
7
' H
2
+' +H
9
and CN
9
("yanide).
N!"leophili" -!bstit!tion
(here are 7 n!"leophili" s!bstit!tion rea"tions needed for this mod!le0
Reaction "
N!"leophile0 +H
9
-o!r"e0 Na+H or 3+H
Conditions0 Refl!$' a!eo!s solvent
E!ation0 C
2
H
F
Br ? Na+H → C
2
H
F
+H ? NaBr
/l"ohol formed
))).mattsrevision."om
c c c
Br
H H H
H H H
H
δ
-
δ
+
c c
Br
H H
H H
H
δ
-
δ
+
OH
-
c c
OH
H H
H H
H
Br
-
Reaction 2
N!"leophile0 CN
9
-o!r"e0 NaCN or 3CN
Condition0 Refl!$
E!ation0 C
2
H
F
Br ? 3CN → C
2
H
F
CN ? 3Br
Nitrile formed.
Reaction #
N!"leophile0 NH
7
-o!r"e0 E$"ess ammonia (to prevent f!rther s!bstit!tion)
Condition0 Refl!$
E!ation0 C
2
H
F
Br ? 2NH
7
→ C
2
H
F
NH
2
? NH
:
Br
/mine formed
))).mattsrevision."om
c c
Br
H H
H H
H
δ
-
δ
+
CN
-
c c c N
H H
H H
H
Br
-
c c
Br
H H
H H
H
δ
-
δ
+
NH
3
c c N
+
H
H H
H H
H
Br
-
H
H
NH
3
c c N
H H
H H
H
H
H
Br
-
NH
4
+
Elimination
Rea"ting spe"ies0 +H
9
-o!r"e0 Na+H or 3+H
Conditions0 Refl!$' al"ohol solvent
E!ation0 C
7
H
I
Br ? Na+H → C
7
H
A
? H
2
+ ? NaBr
;orms an alkene from a haloalkane.
Certain haloalkanes )ill prod!"e more than one prod!"t.
E.g. 29bromopentane
(he 2 "olo!rs sho) the 2 different me"hanisms that "o!ld take pla"e.
))).mattsrevision."om
c c c H
Br H
H H
H
OH
-
H
H
c c c
H H
H H
H
H
H
Br
-
H
2
O
c c c c c H
Br H
H H
H
H
H H H
H H
OH
-
c c c c c H
H
H
H
H
H H H
H H
c c c c c H
H
H H
H
H H H
H H
pent-1-ene pent-2-ene
-tr!"t!re of Halogeoalkanes
;ree Radi"al -!bstit!tion
Chloromethane is formed from methane.
-tep 40 &N&(&/(&+N
Cl9Cl bond breaks. UE light breaks the bond.
-tep 20 *R+*/D/(&+N
radi"al ? rea"tant → prod!"t ? radi"al
(his pro"ess "an "arry on and "a!se a "hain rea"tion.
))).mattsrevision."om
c
H
H
c
Br
c
c
H
c
Br
c
c
c
c
Br
Primary Secondary Tertiary
CH
:
? Cl
2
CH
7
Cl ? HCl
UE
@ight
UE
@ight
Cl
2
2Cl
(his forms a "hlorine free radi"al.

Cl ? CH
:
HCl ? CH
7
CH
7
? Cl
2

CH
7
Cl ? Cl
-tep 70 (ER#&N/(&+N
Ho)ever' f!rther s!bstit!tion "an o""!r0
CH
7
Cl ? Cl
2
→ CH
2
Cl
2
? HCl
CH
2
Cl ? Cl
2
→ CHCl
7
? HCl
CHCl
7
? Cl
2
→ CCl
:
? HCl
/nd so a mi$t!re of prod!"ts are formed )hi"h "an then be separated by fra"tional distillation.
))).mattsrevision."om
2Cl

Cl
2

Cl ? CH
7
CH
7
Cl
2CH
7

C
2
H
A
$l!enes
/lkenes "ontain a "arbon9"arbon do!ble bond (sho)n by C%C) and so are !nsat!rated.
(he C%C bond has a high ele"tron density and so attra"ts positive ions or δ
?
(in a polar bond).
&somerism in /lkenes
-(RUC(UR/@
• ;!n"tional Dro!p0 /lkenes on their o)n don>t e$hibit f!n"tional gro!p isomerism' b!t
alkenes and "y"loalkanes do.
• Chaim0 b!t949ene and 29methylpropene are "hain isomers of ea"h other so alkenes "an
have "hain isomers.
-(ERE+&-+#ER&-#
• Deometri"0 (he C%C bond is planar and so rotation abo!t the C%C bond is restri"ted
)hi"h leads to geometri" isomers. (hey have the same "hemis"al form!la b!t different
spa"ial arrangement of atoms.
&f the bran"hes )ith the highest #
r
are on the same side' then a >N> is pla"ed before the
mole"!le name.
&f the bran"hes )ith the highest #
r
are diagonal to ea"h other' then an >E> is pla"ed before the
mole"!le name.
))).mattsrevision."om
c c
H
Cl Cl
H
c c
Cl
H Cl
H
N9di"hloroethene
+R
"is9di"hloroethene
E9di"hloroethene
+R
trans9di"hloroethene
Carbo"ation -tability

-tability depends on the n!mber of "arbon atoms atta"hed to the C
?
.
Ele"trophili" /ddition
/lkenes rea"t )ith ele"trophiles. Ele"trophiles are ele"tron pair a""eptors.
(here are 2 ele"trophili" addition rea"tions needed for this mod!le.
Reaction "
Ele"trophile0 HBr
E!ation0 C
2
H
:
? HBr → C
2
H
F
Br
(he polar H9Br bond is attra"ted to the ele"tron density in the C%C bond. / "arbo"ation
intermediate is formed after the first step of the rea"tion. (he final prod!"t is a haloalkane.
))).mattsrevision."om
c
+

H
H
c c
+

c
H
c
c
c
c
*rimary -e"ondary (ertiary
c
+

&n"reased stability
c c
H
H H
H
H Br
δ
+
δ
-
c c
+
H
H
H H
H
Br
-
c c H
H
H H
H
Br
Reaction 2
Ele"trophile0 Br
2

E!ation0 C
2
H
:
? Br
2
→ C
2
H
:
Br
2
Bromine "an be !sed to test for !nsat!ration.
&nitially' the Br9Br bond is non9polar. /s the C
2
H
:
gets "loser to Br
2
' the ele"tron density in the
bond is repelled by the C%C bond' forming an ind!"ed dipole.
/ haloalkane is formed.
))).mattsrevision."om
c c
H
H H
H
Br
Br
δ
+
δ
-
c c
+
H
Br
H H
H
Br
-
c c H
Br
H H
H
Br
c c
H
H H
H
Br Br
Reaction #
Ele"trophile0 H
2
-+
:
(s!lph!ri" a"id)
E!ation0 C
2
H
:
? H
2
-+
:
→ C
2
H
F
(+-+
7
H)
(he final prod!"t "an then rea"t )ith )ater to form ethanol and s!lph!ri" a"id' so s!lph!ri"
a"id is a "atalyst in this rea"tion )hi"h is !sed to prod!"e al"ohols.
Ele"trophili" /ddition to a -ymmetri"al /lkene
Regardless of the "arbon atom that the hydrogen is added to' the same prod!"t )ill al)ays be
formed.
))).mattsrevision."om
c c
H
H H
H
H OSO
3
H
δ
+
δ
-
c c
+
H
H
H H
H
OSO
3
H
c c H
H
H H
H
OSO
3
H
c c
H
H H
H
H Br
δ
+
δ
-
c c
+
H
H
H H
H
Br
-
c c H
H
H H
H
Br
Ele"trophili" /ddition to an Unsymmetri"al /lkene
E.g. propene
(here are 2 different prod!"ts of this rea"tion and 2 different me"hanisms0
29bromopropane is the maOor prod!"t and 49bromopropane is the minor prod!"t. (his is
be"a!se 29bromopropane formed the most stable "arbo"ation intermediate (se"ondary rather
than primary for 49bromopropane).
))).mattsrevision."om
c c c
H
H H
H
H
H
c c
H
H H
3
C
H
Br
δ
+
δ
-
H
c c
+
H
H
H H
3
C
H
Br
-
c c H
H
H H
3
C
H
Br
49bromopropane
c c
H
H H
3
C
H
Br
δ
+
δ
-
H
c
+
c H
H
H H
3
C
H
Br
-
c c H
H
H H
3
C
H
Br
29bromopropane
%oly&ers
(here are 2 types of polymerisation0
4) /,,&(&+N0 /ll atoms in the monomer are !sed to form the polymer.
2) C+N,EN-/(&+N0 #onomers Ooin !p )ith the e$p!lsion of small mole"!les.
/lkenes s!"h as ethene are !sed as monomers in addition polymerisation. <hen addition
polymerisation o""!rs' the do!ble bond >breaks open> so many monomers "an add to to the
polymer.
Uses of *olymers
*olyethene is !sed to make t!nnels )hi"h prote"t "rops.
*olypropene is !sed to make fishing nets and ropes.
*roblems )ith *olymers
(hey are !nrea"tive to most "hemi"als and ba"teria so add to the landfill problem.
(hey are e$pensive to re"y"le ("osts of "olle"tion re9pro"essing et").
(hey release to$i" f!mes.
+n the other hand' b!rning )aste polymers "an prod!"e energy and does not take !p landfill
spa"e )hi"h is an advantage.
))).mattsrevision."om
c c
H
H H
H
ethene
c c
H
H H
H
polyethene