SCH4U 1 Organic Chemistry

Part 1 : Alkanes to Aldehydes and Ketones

Saturated Aliphatic Hydrocarbons
Hydrocarbons are compounds that contain only carbon and hydrogen. Alkanes are
hydrocarbons that only contain single bonds. Below are examples of molecular
formula, structural diagrams and ball-and-stick diagrams for the first four alkanes.
methane
I
H-C-H
I
CH4 H
H H
ethane
I I
H-C-C- H
I I
C2H6
H H
H H H
propane
I I I
H-C-C-C-H
C3Hs
I I I
H H H
H H H H
butane
I I I I
H-C-C-C-C-H
C4H10
I I I I
H H H H
Nomenclature
1. Straight-Chained (or Normal) Alkanes, CnH2n+2
Number prefix line structural Number prefix line structural
of C diagram of C diagram
1

t-J.A.
6


e--tV\
;
?..
J\tpt

2 --
7
3
yrop

8
oc\-
/V'VV'
I 3
4
btA+

9
(\ 0 (\
/VVV\
'
5

10
d_Q_c
/VVVV
1
2
2. Branched Alkanes, CnH2n+2
alkyl branches halogen branches
methyl lf flu oro-
-
I+"' c
r-
I
lf
ethyl t]
4 c ->
' (
rl H-
bromo-
Br-
propyl

rt
H
I :

H H ,4
iodo-
T-
isopropyJ.f- fj M rt
-c- c- c-
H {-- I+
cyclopropyl-

. " /7
I C
- ...... c/ \
1-t
Order branches to give them the lowest numbers possible. The longest chain is the
arent. Name the branches al habeticall .
2-methylhexane
Name these:
q- 1-3, 3-d i JCChr\ e
4-ethyl-3-methylheptane
7
/b
).lJ_); 4 -7-
- p R>p ) d e cct ll'\ -e.
3
. Alk C H2
3. CycliC ones,
n n

D
0
0


c\cpert:ln e
dohek:aate
Order branches to give them the lowest numbers possible and number according to
the alphabet if possible:
1, 1-dimethylcyclohexane
1-ethyl-2-methylcyclopenta ne
Name these:
172, y' s-- j- 3,-s.-d.l
. hQ l(ctf\_e_
Chemical Reactions
1. Combustion
Complete combustion:
Incomplete combustion produces a mixture of:
2. Substitution by a Halogen: Only happens in light, as the mechanism needs a radical.
It produces two products- an alkyl halide and a haloacid

hv
/f-c-H +
I
CJ-Cl
l}v H
Cl -t Ct C-+v0o e_ J

CliO) c \-\tt J-J.-c .. + i+ct
t4

I+ - + c l e-
i
r:---1
1-'\
I

I
If
More than one substitution can occur on same molecule:
hv
CCit..t -+
( L{ ClJ-- Cl $ )
A mixture of products (constitutional isomers) can occur when there is more than one
carbon in the molecule:
C4H1o + 2 Cb hv Cy H?:; + ltC I C' ct C/
4
c1 c' ct c
1
c 1 \ 1
1
c1 , , I c I L c-c.-c-c_ e-c-c-e
i C (_;- c-c -c_. C - L -C-- . c- c- (_ - I \
c-c..-c- , 1 ' I ct
1 ct l' \ " . j
Cl d' h\ . :1
1
3
--o\lc\\\oro ) 1
1
L\-c 0"1 )
1
> t-cttcV\\ofO-tA.N<..-; 1,2- 1c oro-t-v\.
1
) ".}.J\ >
1. Fill in the table below for substitution reactions:
reactant(s)
b)
reactant(s)
+ 2 HBr
Type of reactionc:) 5 ct.bsfi-k\-{OUI
hv
1/:,c '---- / CHs -+ 1-lr
I
product(s)
Type of reactionc:)
5
QV:,siitu_ hDt11 .
2. What products would be formed in the reaction between cyclopropane and
chlorine gas in the presence of light?

Without light?
f\0 IX W
m&lca..Ul

5
Textbook: Sect 1.2:Hydrocarbons p. 11-15 Sect 1.3: Reactions of Hydrocarbons p. 24-25
Practice p. 15
1 Write the IUPAC names for the follow1ng hydrocarbons:
a)
CH3
I
CHs CH2
I , I > 1; -,
H3C-CH-CH-CH -CH -CH2-CH3
t 1- I '-t I
CH3 CH3
c) 2- t
CH2-CH3
I ) 6 1
H3C-CH -CH2-CH -CH2-CH -CH3
:, 4 I I
CH3 CH2-CH2-CH3
'i5 cr l ()
2. Draw a structural dia ram for each of the followin h drocarbons:
a) 3,3,5-trimethyloctane b) 4-ethyl-3,4-dimethylheptane
7
c) 2-methyl-4-isopropylnonane d) cyclobutane
D
({ 1
6
7
Unsaturated Aliphatic Hydrocarbons
Unsaturated hydrocarbons have double and triple bonds between adjacent
hydrocarbons in the chain. The electron density of these double and triple bonds make
them a site of chemical reactivity. Interaction of light with the double bonds can
produce vivid colours:
CH3
lycopene- red of tomato, paprika and watermelon
Nomenclature
1. Alkenes, CnH2n. The double bond takes priority when numbering the hydrocarbon. If
there is more than one possible location for the double bond, then locator numbers
must be used.
H H H H H H
'c==c/
" /
" /
/ '
/C=C, /H
H /C=C,
H H
H /c"-
)" H
H H H Br
ethene propene 3-bromopropene
H ~ = = C H - C H 2 - C H 3 H3C -CH ===CH -CH3 H
3
C-CH2-CH==CH-CH
3
1-butene 2-butene 2-pentene
Double bonds are made with one sigma and one pi bond. Pi bonds are formed with
unhybridized p-orbitals which have two lobes- one above and one below the sigma
bond.
The two lobes of the p-orbitals overlap
above and below the C-C sigma- bond.
This forms a pi-bond that prevents the
bond from rotating.
C:[He]
1 1 1 1
sp2 sp2 sp2 P
a bond a bond a bond :rt bond
Because the double bond cannot rotate, the geometry of the bond is locked in place.
This causes the formation of geometric isomers:
trans-2-butene cis-2-butene
Name these alkenes. The longest chain containing a double bond is the parent. A
chain containing two double bonds ends with "diene".

2.. l4;
3,3 _ d \ rY\eth lj 1-i - b GlTel\ e
S - -d - -
- pe_(\\Q_ \'\, !(
Br
'1--#)
4-
-1\ .e rtos\ ed( eO\.(>
2. Cycloalkenes, CnH2n-2. The double bond always takes Cl and C2. When there is
more than one double bond, number the ring to give them the lowest numbers.
8
3. Alkynes, CnH2n-2, remember the linear geometry for four atoms in a row
I 2.
I 2 ]
H-C==C-CH
3
Chemical Reactions
1 . CombustionS
C2H4 + 02 -
2. Addition: Here an entire molecule adds across the double bond, so there is only one
product. The electron density of a double or triple bond makes the bond vulnerable
to attack by:
a) halogens (F2,Cb,Br2,b): are very electronegative so they can attack with no
catalyst or light needed
Cl Cl
I I
J./--c-c-1+
'-) Of\.J
?PGbu.LT
r 1
tl H
C. I --- (l
Cl Cl
i l
H-c-c-14
( I
+l 1-i
C - Cl -7 i+- C.:_=._ --c_ -J-1
I I
rl 1-\
-}
c_ \ J-- etttv..-dcs
c\ C:: c_
11 wru1 \wo
C s t'J i'.v:tiLS
9
I,
-')
,;!..
H
b) haloacids (HF,HCI,HBr,HI): two H+ and x-: the positive H+ ion is the one
attracted to the double bond, so 1t attacks first:
'- /H
c-c
+ HCI
t-t Cl
I I
..,. -C..__ C -I{
/ \
H H
I I
t-1 H
10
W oJ\v...d<'-s douVJI.Q_ bond boih e.- c.(, bu\'\.Li cv...Q_ -fi-r;.n .. .&)

0- -\-\ -)
! I
l-t 11
1-1
G)
H- c- c-it
\ I
H
[ClrDOill -\10 V\
bo We , e- "b 'tt\L 'n bo.'\ll -\t'-l. two .raAlJ(wl- c::u-
-\D 4t\Q HiliM . 141\ bi!V\1
C\ _-to !-\ Ef? cU 1
\)D"''1f.\.W.. Dl\ 1-\W c
--+t\R+ I M + -B-s 11 c -lD --\t0.. f\ILw b 61'(1 iJJ rWW pdch
mt1ov'v C/B
} '
s L l - cct1a_dcl. ,(UAL) o ca*tuVl,
H /GG
T ()
.

1-)
i
H-
I
1-t
e-
/ -f6v1. Cl-

I
c -\+
I
li
When a molecule is asymmetric about d 11
applies (the rich in hydrogen get richer then Markovnikov's rule
Cl 4
HsC
" /H
I \
c h3- c- c_-1+
c==c + HCI
H/ \
H
' l
H
0 [\)l y
}ht<;
ISOt!Y\-e,-

;J. " a .. \-\ cu1cs c cl ou IGI-e bO'i\c\ ; 11 b u'a tu,..
-, wo pos<;'1

---
.- -
f \
c__- C -f -l+ , o R
3 .
I I
H (. H
'-
f
3N\ct \\ere \e&mA
c\ou_d c-
I
H
-1'
e\ec.Wvt
H3 c - c
I
lkts rnrbocaJ!cl'A Is s-taloiU2Q_d
bette!' by Lal!j.e>D e_ie.droil c{GU.[I
?o lasts 3ni
C\- 01 ..
(j;) '.+
H;c- c- c -t+ +

-0
Cl ir-J
I I
I
' ' - c- c -.}{
1SL I )
! I
rt H
rl d
14 S-ttA ---tko. mas.+ i-l
'--14 QK-h t-1 . <3, .e:+ r-Ich e I'-
12
c) water: not able to attack on its own, it needs an acid catalyst
H3C"' H
c===c/
/ \
H H
-I'
0 X [j 3 til. (lj:ul\
1
t
bO'I\Cl'
::. 1'-
11- 0; 4
{ l
H c- c - c +
3 I 1
t
M H

+

f.
13
d) hydrogen: not able to attack on its own, needs a metal catalyst (Pt, Ni, Pd)
HsC'\. H H )-4
c==c/ i ; .
/
+ H2 metal H
\ .. t-\; (_ -- c - C_ -
H H i j
H-H

f'0.- e 1-oJ s Ll t'- f?a.c -'

l-i H
H---
H -1-\ -PcN\'lS LDt- bOV\tD w
(\\ S e c fu c;
-+4 ti H horJ .
) . ffi. 1\LW -to --trAQ. 1-( - -l-1 , wd its It 0iJI\J bV'eaiC!
++
( (

-)
Fill in the blanks for the followin reactions:
1.
)ycl
lvLel
+Cb
product(s)
Type of Reaction Ac\d \hoV\
2.
C) H+
Type of Reaction
P1dcti n\ov1
3.
reactant
Type of Reaction
product(s)
Cl
Cl
14
t\J\a!'I(QUn t l S
l'lk \ -e
Textbook: Section 1.2 Hydrocarbons p. 16-18, Section 1.3 Reactions of Hydrocarbons p.
25-27 Practice p. 18
5. Write the IUPAC names for the compounds with the following structural diagrams:
a) b)
CH
3
7cH
3
t "l. ) ul )- (D I
H ~ - c = = c -CH -CH-CH2
I
CH2-CHJ
15
c) d)
e)
4 3
6 D t t I d" f raws rue ura 1agrams or eac h f th f II d 0 e o ow1ng compoun s:
a) 5-ethyl-2-methyl-2-heptene b) 1,3,5-hexanetriene
2..


'1

({_
I
..,
-::::::---
c) 3,4-dimethylcyclohexene d) 1-butyne
l
Q
t 2.

-
e) 4-methyl-2-pentyne

Practice p. 27
1. What compounds will be produced in the followin addition reactions?
+ HBr
c)

I
+ H20
H
3
C'-...C/CH........_C?CH2
H2 H
d)
0
+Ch
H
Pt
J
It
l
Hs C - c._ -
I
H


tH2CH3
+-1 br---
f I .
-----. J-\3 C- C- c - CHz_ -CHs
I !
It c 3
t"\ ct!t( D V V\ t \(O\l N.JJ J<_
c i-\z. c c th.
H+
I
... H c Y '--t
3
c"'
c_ l (
OH
1-f
t<o\rs
fl {A\ -e
...
C!
C.. I
16
3. Draw structural diagrams to represent addition reactions to produce each of the
following compounds.
a} 2,3-dichlorohexane
b) 2-bromobutane
C/
i
: : : > ~ G
Cl
Br
--) 1 ~ 4
M
M etr- !.{oV 1\ I ko v \:; 7< u ~
c) 2-hydroxy-3-methylpentane
17
Aromatic Hydrocarbons
H
c
HC/
II I
HC........_
c
Aromatic hydrocarbons are based on
benzene ring, C6H6.
H
A benzene ring has a cyclohexane
'skeleton'. Each C-C bond and each C-H
bond is as bond. So each C has three
hybridized sp2 bonds it uses for single
bonds. The result is a planar (flat) ring.
H
H--=o;___ _......;o;;.__ H

H
Each C in the ring also has an
unhybridzed p-orbital. The two lobes of
the unhybridized p-orbital extend above
and below the ring. These p-orbitals are
used to make three p bonds above and
below the si ma bonds of the rin .
The cyclohexane ring is unique in
that it puts the six ring carbons
H-- --H close enough that their p-orbitals
, n are all able to overlap with each
U other.
H--
c
H
18
H H
e e
He
/ ~ e H .b'
..........: H e ~ "'eH
II I ~ ~ , . . . . I II
He, .beH He=--.. eH
........ ~ /
e e
H H
A benzene ring is often drawn as a
cyclohexane ring with a circle in the
middle. The circle represents the
delocalized n bonds.
Note the six Hs are not shown.
19
Because of this the three n -bonds can keep
shifting position. In fact the three n -bonds are
continuously moving. You say that then -bonds of
benzene are delocalized. This delocalized n
bonding gives a great stability to the benzene ring
-it is very much more stable than a simple
cyclohexene ring, and much more stable than a
cyclohexene ring with three ordinary (not shifting)
n bonds would be.
H
A diagram of a benzene ring might look like
the one above. Because then bond has
two lobes, benzene forms two circles of
delocalized n bonds- above and below
the rin .
Nomenclature 1 . Benzene as the parent
0
benzene
1,3-dimethylbenzene
meta-dimethylbenzene
m-dimethylbenzene
methylbenzene
(toluene)
1 ,4-dimethylbenzene
para-dimethylbenzene
p-dimethylbenzene
1,2-dimethylbenzene
ortho-dimethylbenzene
o-dimethylbenzene
1-ethyl-2-methyl benzene
o-ethylmethylbenzene
20
2. Benzene as a branch: When benzene is a branch, it is called a phenyl branch. It is
not iven any special status over other branches.
Br
5-phenyl-2-heptene 3-bromo-2-methyl-4-phenylhexane
CH3 CH3
!- d. -!l l-\i'bOO\zel1 e
D - fY\ e\h 11)\+ro\JJ-eU\:4? II J
N02 ' lr-.
-M -m fltTrci/Jer t\ t?
Cl

- \he \fun e.
o - r. Hn:rto Lu__ en t>
,'-4, e
(T.N.I.J
Chemical Reactions p. 28- 30
1 . Combustion
c6H6 + i o2 - {Q cod.._+ 3A2_o
d c + 1S' o d,_ t). t b\z. 0
Br
2. Addition
Br
Addition cannot happen because
of the strength of the delocalized
pi bonding.
3. Substitution can happen, but only with a catalyst:
of a halogen
11 AICI3
+
It
I
M
1
, , , , 0 , 6
t.\.7e_ tlCjht! C\a >r 7 Cl i- f"i)C\t{ ,
b) of an alkyl group (using an alkyl halide)
+
LJ
J
Cl
Hc1
21
c) of a nitro group (using nitric acid)
H
H
7 I H2S04
ff ' I+ ff /
0
....._ H
H
@ 1'\1.18 n-\ J) 1 I (J
H 1-00
3
-) -run . 1\)oP-' tAi)) H- iroN\ 01,'B
I CL) t\0
Fill in the blanks for the followin reactions:
1.
FeCb
Cl
reactant(s)
Type of reaction Q 5 Ltl)sti+u -Ho ll
2.
@Jr
Cr\:3C\b_CI
FeCb
reactant(s)
Type of reaction Q s l\ \:)sti+u. -ho V\
N02
3.
e t d. Hi'J03
H2S04
reactant(s)
Type of reaction Q
s lJ\ \i o V\
22
+ H;z_O
-1'
H- + frum beff\2ll\e
oH- -RoM HNOs
+ 2 HCI
+ HCI
+ 2 H20
N02
23
Textbook: Section 1.2 Hydrocarbons p. 19-21, Section 1.3 Reactions of Hydrocarbons p.
28-30
Practice p.21
4. Draw a structural diagram for each of the followin hydrocarbons:
a) 1,2,4-trimethylbenzene b) 1-ethyl-2-methylbenzene
0
c) 3-phenylpentane d) o-diethylbenzene
e) p-ethylmethylbenzene
{
@
)
'I
24
Practice p. 30
4. Predict the product or products formed in each of the following reactions:
a)
0
+ Cb AICb
..
..
product(s)
b)

N02


H2S04
.... t-
+

HN03
product(s)
5. Propose a reaction series that would produce 2-phenylbutane, starting with benzene
and 1-butene as reactants.
Ac\d.\h"D
/ ]-\-
-c. [-\- c
I
-l
I+

S lA.\os +LL \io
-t HCI H-
c-
(
It
Cl
I
C- CHz_Crt3
I
H
Ytat"kov 1\ \<'ou's
w
i
c - c

:2. C\13- c
I
Cl
Alcohols
The functional group is the hydroxyl group, -OH. The carbon that the hydroxyl group is
attached to, C-OH, is called the carbanol carbon.
Physical Properties
25
The hydroxyl group enables an alcohol to have hydrogen bonding. A small chain
alcohol dissolves well in water. The R- group of an alcohol is a non-polar hydrocarbon
chain. You need one hydroxyl group for every 5 carbons to enable a large alcohol to
dissolve in water.
The hydrogen bonding of water gives it a higher boiling point than a comparable
hydrocarbon.
Nomenclature
Alcohols rank over alkenes and alkynes in nomenclature.
H
3
C-OH H C-C-OH
3 H2
rn
e l
OH OH
I
!
H
3
C-HC-CH
3

C o\cd\ol)
clopropctf\ o \
OH
HC-HC-C-OH
3 2 H2
l -o I
C n -pi'DP/j l oJcd\Ol J
OH
OH
pn-\ctn e-d
1
3- cHo I
OH
1-/"i\ c -l-
i c\j c\opev1\uncJ)
Chemical Reactivity
The position of the hydroxyl group determines some of its chemical reactivity.
OH
OH
I
H
3
C-CH
2
-0H
I
HC-C-CH
H
3
C-CH-CH
3
3 I 3
CH
3
a primary alcohol a secondary alcohol a tertiary alcohol
(a 1 alcohol) (a 2alcohol) (a 3alcohol)
1. Combustion
2. Elimination: happens in 2and 3alcohols in the presence of concentrated acid,
such as cone. H2S04 to form an alkene.
)0
H -C. - c- c t-h
I ;
H H
cone.
H2SOy
h e-tt
I, 4. Q Oct:

I
1-t
t-l- c_ :::::. c. _., c t\ 3 + r-h __ 0
\ l
/-t c r\;,
26
27
3. Condensation: an elimination reaction between two 1 alcohols only to form an ether,
this again uses concentrated acid as a catalyst. u
.LJ CO(\.( rT
;) + Hz_O
I I
H H
4 --- - 1-l
I 1 ' I 8
c H3 - - c,O- +I + _lf-@)- p -C\-\z_[l-\3 -) CH)-CHz- C-@ -C\--\2_ c
If - - - - H '
li + Hz. o
l t- tl\)1'(\ o. dd r es () H Oh tho oec;J'bo Cbr\t0.1 t.>r, 0'1\1 q '\fAQ_
4. Oxidation: uses an oxidizing agent such as furns from purple to green
to brown as it oxidizes a substance. Oxidizing agents can be written as [0].
+
[o]
-+ 0
1? c a r-b0X Ltc
C

C@ + [oJ -7 -Ol-\
CUJ. t C o]
f'ffi.c-\i:UV\...-
n&_ fR__QC--ttCN\
1
\ t (()'{\_tfcl\ed
1
OJv\.
Co] , lt'&JVV iJJ crx l-6-- n..
0-A Y:fJC ,(\ t_,tc) -
'uJ Cm\pUcoe_d.
_ WuJ0 :
I'") c d.- 3t
I & ti-t + o<. 'a-o, + 3 0 0 f-t -=) Li Cr + 3 CH3 [ 00 t\ i Ji 2- 0

[o] I' olcd\D I
b} of a 2alcohol
OJ+
I
C l-is-- c.. - c H.>
I
c H '"' : J
-1' t\Ua
28
-t C oj
i!e t-on .e
CQf'bo..r\cl tt CL!J
\4JVl'V_ .J.h_
rto MDrz H .
c) of a 3alcohol

i
c -
I
C+t3
Reactions
+
Fill in the blanks for the following reactions involving alcohols:
1.
OH
H+
Type of reaction I:}
+l4zo
I
Product(s}

29
2.
OH
+ (0)
Product(s)
Type of reaction c)
cYX ( ru-n-c))!\_
3.
H+
reactant(s)
Type of reaction c) f f i ~ ~ U ~
4.
/-fz_O +
H+
OH +
\ o ()lco1Jv;{s.
Type of reaction c) CO{'diN\hcUtol)
5.
H+
reactant(s)
Type of reaction c') ~ a.:\ eM..
6.
H +-b.
1-\3( "- I / C '\ 61-\-
C C:
i ( "+i + (0)
OH H
reactant(s)
Type of reaction c') C))<( c\ Q ti 6 Y\
Textbook: Section 1.5 Alcohols and Ethers p. 38-44
Practice p. 41
1. Write IUPAC names for the following compounds:
a) b)
H2 H2
H3c........._ /c.........._ /c.........._
CH C OH
I H2
OH
30
c)
OH
2 E?l'\ I) 3-d 1'0 t
( 3 - f\ CJ pi"'!L not )
2 D t t I d" f raw a s rue ura 1agram or:
a) 3-methyl-1-butanol
(3-methylbutan-1-ol)
!+ 1-1
CN> 4
I
I I
1
11- c.- c-
C- (_-It
I I

1-+
c) glycerol (propane-1,2,3-triol)

1-\
of.\
I
)
I
1+-
c.. - c-)-\--
I
1
I
H
OH H
31
b) 1,2-propanediol
(propane-1,2-diol)
Of-\
H
1'-\-
I
I

J-J-C- c.-
I I
l
M
ou
If
d) phenol (that is its IUPAC name)
Of-\-
@
3. Draw structural diagrams showing:
a) an isomer of butanol that is a secondary alcohol

I
-c-c.-C..-c-
1 I
b) all the pentanols that are isomers Oi-\
01-\ , I r I 1
I . ,c -c -c -c
, c -C I ' I I ' I
ort
\ I \ \
-C- c_-
c_- c_
\
Practice p. 42
4. Explain briefly why methanol has a higher boiling point than methane.
J!l e_ -\it\ a lA e t'il ethel l
M
I
J-t- c- 0 l{
'
1-t
L t t-s
IJoiVc 1---'6fS C\ft\d
5. Arrange the following compounds in order of increasing boiling point, and give
reasons for your answer.
a) butane b) 1-butanol (butan-1-ol)
1" j\
lowes+-
f't est cha ( 1\
5

0
'+ n
H- bOMlY\Ol
L-- b Fs on\y + 1--. bt-c;. -a
32
Practice p. 44
7. Alcohols can be made by addition reactions.
a} Draw structural diagrams to represent the reaction:
2-butene +water- 2-butanol (butan-2-ol}
OH H
I l I
c -c_ --::: c - c..- + Hz_O
1 I 1
1
- c_- c - (__
t '
8. Elimination reactions of alcohols are generally slow, and require an acid catalyst
and heating.
a} Draw structural diagrams to represent the reaction:
6H
I
1-t - c._-
I
H
p i--l
I
c - c -
ll
l
H
1-propanol (propan-1-ol} - propene + water
COif\_(_ f/
, I I + 1\ Ju'
c = c - c_ - )-;- i t.-
H / J
If It
33
)0.1\_u_ jp, o_ (Oi'l I A
fuv'-- t \-\L-0 -1)2r
9. Onlylb few of the simpler alcohols are used in combustion reactions. Alcohol-
gasoline mixtures, known as gasohol, are the most common examples. Write a
balanced chemical equation, using molecular formulas, for the complete
combustion of the following alcohols:
a} ethanol
I \
-c- c - ot-\
b) propanol
I I ( 3
c - c - c -01-f + Q-,
I I d. d
Practice p. 45
10 b) What are the advantages and disadvantages of methanol as a fuel, over
more conventional gasoline or diesel fuels? (Google this)

_ 0\.rlt\DJI!\{yt) o \-\
1
6()
C)d-. to
tvv'\ LM fttJvv\__ f--f.
CCXI\
-- l.1
1
-6 [A_
/) i'Y\d)j__
ll;s
ih
- 1Jooclt , _ t-01'1\ , \-o Mill<'L

1
ifta\-e .
34
i;l; 1o
Ethers
The functional group is an ether linkage, -C-0-C-
Physical Properties
The C-0-C gives a bent geometry. This creates a small area of polarity within an
otherwise non-polar molecule.
35
The bent geometry also hinders ether molecules from getting close to each other
to form good intermolecular bonds. Therefore ethers have a low boiling point and
evaporate easily.
e.g. CH3CH2-0H: bp = 80C CH3-0-CH3: b.p. =-25C
Nomenclature
In an ether, the larger R group is named as the parent, and the smaller R group is
named as an ether branch.
Ether Branches

0
H3C-0 H
3
C-H
2
C-O
I

methoxy ethoxy phenoxy
Br
0"-.--
methoxyetha ne
d-- b{C)YY\0- l:t (\
l
OH
0--o
& -PNL (\ o-x _0- -;- t
Chemical Reactivity:
Combustion: The high volatility (ability to evaporate) of ethers makes them
dangerously flammable. As they mix with 02 in the air, the smallest static
spark can cause an entire room to burst into flame.
36
Other than combustion, ethers tend to be chemically stable. This makes them good
solvents: Since they are fairly non-polar, (only the one oxygen of the ether linkage
contributes any polarity), they dissolve most organic compounds easily- and they don't
react with them. The small polarity of their one oxygen lets them dissolve some polar
substances as well- and not react with them. But their small polarity is not enough to
allow them to dissolve in water, so they can be used to extract non-polar substances
from water. They have no acidic hydrogens, so again they can dissolve substances that
would react with an acid. Because of this, ethers are used as solvents in many reactions.
Textbook: Section 1.5 Alcohols and Ethers p. 45-48
Practice p. 46
11. Write IUPAC names for the following compounds:
a) b)
Practice p. 48
12. Like many organic compounds, alcohols and ether undergo complete
combustion reactions to produce carbon dioxide and water. Select one
alcohol and one ether, and write structural diagrams for their complete
combustion.
Ct-\.3 -(\-\z -0+\ + 30.:{ -) ) CO a -t 3 t-\z.O
C ~ : , - 0 - C ~ - s t 30d ---;:, o<COa -tSI-hD
Aldehydes and Ketones
The functional group is the carbonyl group.
Aldehydes have the carbonyl group at the end
of a chain.
Ketones have the carbonyl group within the
chain.
Physical Properties
0
II

0
II

37
The oxygen is not bonded to a hydrogen, so neither aldehydes nor ketones can
form a hydrogen bond with themselves. Because of this, both have lower boiling
points than a comparable alcohol:
A ketone has a higher boiling point than a comparable aldehyde. You would
think the aldehyde would be more polar than the ketone and so have the higher
bp.
The carbonyl group is more polar than an ether linkage. So small ketones and
aldehydes are soluble in water.
Nomenclature
Aldehydes rank over ketones (perhaps because aldehydes are more reactive)
and both rank over alcohols, alkenes, alkynes and ethers.
Ketones
propanone
L\-r
3 -0\.Q
butanone 4-hydroxybutan-2-one
0 0
A
38
Aldehydes -locator numbers are not needed since the carbonyl is always C
1
0
II
HsC-CH
Br
ethanol 3-bromobutanal
0



I
5

$-\f\ 1-L\ -ll'Xo PQniQ f
T these:
a) b) I
0
0
d) e)
0
0

1- P -J: Cf\ e 3-b u-\.e_V\ -1-oi\.0
[ 1- phl\\j i prtj:tm l1he]

OH
3-hydroxybutanal

o.J
J -rn p rop:tl\ e.d 0J
c)

0
f)
Cl
0
l _ ch -I) 3-d\ me tw XJd -

Chemical Reactivity
1. Combustion
2. Oxidation
Aldehydes: have a carbonyl hydrogen which can leave as part of an oxidation
reaction.
Ketones: no leaving H on carbonyl carbon
+ [0] -+/-:.... f\o t-X
I


3. Addition (Hydrogenation): Addition of H
2
across the C=O double bond. This
needs a catalyst, heat and pressure.
Aldehydes: a primary alcohol is formed:
catalyst

he-al pressure
0 - -- - t--\
I; .
C-- .. H
1-t
0
I
H3C., /Y--- H
c_ J-1
H;)._
39
Ketones: a secondary alcohol is formed:
cat alyst
heat pre.ssure
0 ---
I i I
H3 c c ----
\
-l-1..2 Cti.3
Fill in the blanks for the reactions below:
l.
reactant(s)
2.
OH OH
+ [0]
Type of t:n<'t
+ [0] ...
0
I
0
[I
product(s)
Type of Reaction lOQ -t\01\
40
41
3.
t-k-c-o\-\

+ [0]
HC-:;:::::::.O

reactant(s)
Type of 0 X'lc\O..t\0 VI
Textbook: Section 1.6 Aldehydes and Ketones p. 49-56
Practice p. 51
1 D t t I d" f h f th f II d raws rue ura 1agrams or eac o e o ow1ng compoun s:
a) ethanol b) pentanal
0
0

t
t
r 'ioJ
L tbC t-\
c) hexan-2-one d) phenylmethanal (benzaldehyde)
0
-'lo t I

@
3. Write the IUPAC names for the following compounds:
c)
Practice p. 52
4. Write the IUPAC names for the following compounds:
a) acetone b) formaldehyde c) acetaldehyde
pro }:0-no lf\ --e
D
II
(_
/'
-c.-- -e..-
1
42
5. Arrange the following compounds in increasing order of predicted boiling points and
give reasons for your answer.
a) b) c)


43
Practice p. 56
6. Draw structural diagrams and write IUPAC names to illustrate the controlled oxidation
of the following alcohols. Is the product an aldehyde or a ketone?
a) 2-pentanol
0
+ [o] -)
b) 1-hexanol
-r Co]-)
7. Predict the relative solubility of the following compounds in water, listing the
compounds in increasing order of solubility. Give reasons for your answer.
a) b) c)

cwJ)
polo-r-
rv\rot
{ A YY\_QJJ.. '



.. ))6tD- 0'- )
44
SCH4U: Hydrocarbons Practice Sheet
1. Give the correct name for the followin molecules:
1. 2.
l
3, 4.
s
5. 6.
7. 8.
9.
11.
13.

'-.
2- fs-
&
Lt-bu-\- \- 3 -c -I) L\ -
- h e__-xM Qd \ Ql\ e
I
)- -;A- 1-1; s--
- e
15.
17.
10.
12.
14.
16.
7- b1C5mt) -3- M
, ),_ I
o;
, )
'0
q
l- I - f1 01\ eU\ .Q
18.
45
2. Reactions: Fill in the missing information:
Fill in the missing information for each of the following:
1.

2.
+ HCI
3.
:I
hv
t-M-r
I l)-.t (J{\
Product(s)
Type of Rx: 5
Conditions
necessary for a
Rx Cl
Type of Rx: t\V'\1\;
Product(s)


Reactant(s)
Conditions..,
necessary for a
Rx
Type of Rx: o..._cUi:tbn
Product(s)
46
4.
+
Reatant(s)
5.
Reactant(s)
Br
2
Conditions
Necessary
1h br coot&
Type of Reaction: S
+ HCI
1'\01\9-
Conditions
..
Necessary
Type of Reaction:
00-dit\01\
Product(s)
47
1. Nomenclature
a)
c)
e)
g)
Grade 12 Chemistry: Organic Practice Sheet 2
b)
OH
d)
OH
f)
h)
0 OH
Q
0
OH
0
~
0 ~
OH 0--
48
i)
k)
m)
Br
o)
0 0
,lX),
'L
j)
I)
1- 3--
' 3-eth
n) .
0
p)
0
49
2. Reactions .
Fill in the boxes for the followln reactions:
a)
Reactant(s)
b) Cl
'@>oM +
Reactant(s)
c)
0

(

0 I : :
ll :
c -7 .-c._- 1-l
L " I
necessary
conditions
Type of Reaction:
H+
necessary ..,.
conditions
Type of Reaction:
necessary ..,.
conditions
Product(s)
Cl

Product(s)
Product(s)
Type of Reaction:
50
d)

[0]
Reactant(s)
e)
f\(5\'\Q
necessary
conditiont
Product(s)
Type of Reaction:

necessary
conditions
OH
0 0
Reactant(s) Product(s)
f)
0
+
Reactant(s)
Type of Reaction: ()t<\do_no/\
necessary
conditiont


HaO
Product(s)
Type of Reaction:
:s Q\os+lk \-i of\
51
g)
Reactant(s)
AlCis
necessary
conditions ..,.
Type of Reaction:
+ HCI
Product(s)
5 Gt b0 +1 +u,_t-\Of\
52
3. Order the following substances from lowest to highest boiling point: pentan-2-one,
pentane, pentan-1-ol, hexane.

L
I P.eNt 1ruv\ -;) --o Y\ {)
L
peY\bM_-1-ol
a
H-o-c -c-c -c-c
--e -c -c -c
II
C-C-C -c-C.
c__ -c -c -c -c
LDFs

QipoG_- cDp0U



L \) "fS,