Download SCH4UOrganicWS ans - SCH4U1-CCVI

ALKANES
1. Draw structural formula for:
a) 2,2,4-trimethylpentane
CH3
CH3
CH
b) 3,4-diethylheptane
CH3
CH2
CH3
C CH3
CH2
CH
CH
CH2
CH3
CH2 CH2 CH3
CH2
CH3
CH3
c) 3-methylheptane
d) 4-ethyl-3-methylheptane
CH3
CH3 CH2 CH2 CH2 CH CH3
CH2
e) 3-chloro-2-methylhexane
CH
CH2
CH2
CH3
CH3
CH3
C CH2
CH2
CH3
CH3
g) 4-bromo-5-iodo-2,2,3-trimethylhexane
h) 5,6-dichloro-3-ethyl-2,3-dimethyloctane
CH3 CH3 Br
C
CH2
Cl
CH3
CH3
CH2
f) 2-chloro-2-methylpentane
Cl
CH
CH
CH3 CH2 CH3
CH3 CH2
CH3
CH
CH
CH3
CH
CH3 CH2
CH
CH3
CH3
I
CH
C
Cl
CH2
CH
CH3 CH3
CH
CH2
Cl
2. Draw and name 3 isomers of C5H12.
• have the same chemical formula, but different structures – different branching.
C
C C C C C
C C C C
C C C
C
n - pentane
2 – methylbutane
C
2,2-dimethylpropane
3. Which compound has the higher melting point: propane or pentane? Explain.
n – pentane has the higher melting point as the molecule can pack closer together causing stronger
London Dispersion forces. More energy is needed to overcome these forces and allow the molecules to
move further apart and melt.
CH3
ALKENES
1. Draw structural formula for the following:
a) 2-methylpropene
CH3
C
b) trans-2,3-dibromobut-2-ene
Br
CH2
CH3
C
CH3
C
CH3
c) cis-hex-3-ene
CH3
Br
d) 2-ethylpent-1-ene
CH2
C
C
H
H
CH2
CH2
CH3
CH3
e) cis-4-chloro-5-methylhex-2-ene
CH2
CH
CH2
CH2
CH3
f) 4,4-dimethylhex-1-ene
Cl
CH3
C
CH2 CH3
CH
C
H
CH3
C
H
CH3
CH3
C
CH2
CH
CH2
CH3
g) trans-3-bromo-2-iodo-4,5,5-trimethylhex-2-ene h) trans-3,4-dichloro-6-ethyl-6,7-dimethyloct-3-ene
H3C
CH3 CH3
Br
C
C
CH
CH3
C
CH3
CH3
I
CH3
CH2
CH
C
CH3
CH3
Cl
CH2
C
C
CH2
Cl
2. a) Draw and name the geometric isomers of C2H2Cl2.
H
H
C
Cl
Cl
H
C
C
Cl
cis-1,2-dichloroethane
Cl
C
H
trans-1,2-dichloroethane
b) Which of the two compounds above has the higher melting point? Explain.
cis-1,2-dichloroethane has the higher melting point as it is more polar than the trans isomer.
CH3
ALKYNES
1. Draw structural formula for the following:
a) 4,5-dimethylhept-2-yne
CH3
C
C
b) 3,3-dimethylbut-1-yne
CH
CH
CH3
CH3
CH2
CH3
CH3
HC
C
C
CH3
CH3
c) 4-methylpent-2-yne
d) 4-ethylhex-2-yne
CH3
CH3
C
C
CH
CH3
CH3
e) 4-chloro-5-methylhex-2-yne
CH2
CH
CH2
CH
C
C
CH3
CH3
C
CH3
CH
C
C
CH3
CH3
CH2
CH2
C
CH
CH3
g) 1-iodo-3,4,4-trimethylpent-1-yne
h) 6-ethyl-6,7-dimethyloct-3-yne
CH3 CH3
CH3
CH3
f) 5,5-dimethylhept-1-yne
Cl
CH3
CH2
C
CH3
CH
C
C
CH3
I
CH3
CH2
CH
C
CH2
CH3
CH3
C
C
CH2
CH3
2. a) Draw and name the isomers of C4H5Cl.
There are several, here are a few:
Cl C
C
H
H
C
C
H
H
Cl H
H
H C
1-chlorobut-1-yne
C
C
C
H
H
H
H
3-chlorobut-1-yne
C
C
H
H
C
C
H
H
H
C
C
C
C
H
H
H
H
Cl
1-chlorobuta-1,3-diene
H
C
H
C
C
C
Cl
H
C
C
C
H
4-chlorobut-1-yne
H
H
H
Cl H
3-chlorobuta-1,2-diene
H
C
H
C
C
C
H
H
Cl
H
1-chlorobut-2-yne
H
H
H
C
Cl
H
C
Cl
C
C
C
H
H
H
4-chlorobuta-2,3-diene 1-chlorobuta-1,2-diene
b) Which of the isomer compounds above has the higher melting point? Explain.
1-chlorobuta-1,3-diene has the closest packing as it exists in a flat plane.
Nomenclature for Alcohols
Draw the following molecules:
a). 2-chlorobutan-2-ol
OH
CH2
C
H3C
CH3
Cl
b) 2-methylheptan-2-ol
C
C
C
C
C
C
C
C
OH
c) octane-1,4-diol
OH
HO
CH2
CH
CH2
CH2
CH2
CH2
CH3
CH2
d) cyclopentanol
OH
C
C
C
C
C
e) 2,3,4-trichloro-5-methylundecan-1-ol
CH2
HO
Cl
CH3
CH
CH
CH
CH
Cl
Cl
CH2
CH2
CH2
CH2
CH3
CH2
Nomenclature for Ethers
Draw the following molecules:
a) 1-chloro-1-ethoxypropane
C
C
O
C
C
C
Cl
b) 2-methyl-1-propoxyoctane
CH2
O
CH2
H2C
CH2
CH2
CH2
CH2
CH
H3C
CH3
CH3
c) 1-propoxypropane
CH2
H3C
O
CH2
CH2
CH2
CH3
d) 2-methoxypropane
C
C
O
C
C
e) 7-methyoxyoctan-2-ol
CH3
H3C
CH2
CH
OH
CH2
CH2
CH2
CH
CH2
O
CH3
Nomenclature for Aldehydes
Draw the following molecules:
a) 3,3-dimethylbutanal
O
CH
CH2
CH3
C
H3C
CH3
b) 4-bromo-3-chloro-5-ethyl-2-methylheptanal
CH2
H3C
Br
CH3
CH
CH
CH
CH
CH2
Cl
O
CH
H3C
c) 2-bromo-3-ethylhexanal
C
C
C
C
Br
O
C
C
C
C
d) 4-chloropentanal
e) 2,2,4-trichlorooctanal
Cl
O
C
C
Cl
C
C
C
Cl
CH
O
C
Cl
CH
CH2
CH2
CH2
CH3
CH2
Nomenclature for Ketones
Draw the following molecules:
a) 3-chloro-4-phenylpentan-2-one
CH3
O
HC
C
CH3
CH
Cl
b) 3-bromohexan-2-one
O
C
C
C
C
C
C
Br
c) 3-ethyl-2,5,7-trimethyloctan-4-one
CH3
CH2 CH3
CH2 HC
H3C
HC
C
CH3
HC
CH
O
CH3
H3C
d) 2,2-dimethyldecan-4-one
CH3
H3C
C
O
CH2 CH2
H3C
CH2
CH2 CH2
e) 1,3,5-trichlorohexane-2,4-dione
O
C
C
Cl
Cl
C
C
C
O
C
C
Cl
CH2
CH3
Nomenclature for Carboxylic Acids
Draw the following molecules:
a) 3-fluoropentanoic acid
O
C
C
C
C
C
OH
F
b) 2,2-dimethylbutanoic acid
C
C
C
O
C
C
OH
C
c) 2,3,3,5-tetrachlorooctanoic acid
O
HO
C
Cl
C
C
Cl
Cl
C
C
C
Cl
d) trans-4,4-dimethylhex-2-enoic acid
C
C
C
C
O
C
C
C
e) propanedioic acid
O
HO
C
O
C
C
OH
C
OH
C
C
Nomenclature for Esters
Draw the following molecules:
a) 1-butyl ethanoate
O
C
C
C
C
O
C
C
C
C
C
C
C
C
C
b) 2-butyl propanoate
O
C
C
C
O
C
C
c) 3-pentyl 2-methylbutanoate
O
C
C
C
O
C
C
C
C
d) 3-methyl-1-butyl propanoate
O
C
C
C
O
C
C
C
e) dichloromethyl ethanoate
O
C
C
Cl
O
C
Cl
Nomenclature for Amines
Draw the following molecules:
a) N-ethyl-1-aminopropane
C
C
N
C
C
C
C
C
C
C
C
C
b) 2-aminohex-1-ene
N
C
C
c) 4-chloro-2-aminoheptane
Cl
C
C
C
C
N
d) N-ethyl-N-methyl-2-aminobutane
C
C
C
C
N
C
C
e) N-methylaminomethane
C
N
C
C
C
Nomenclature for Amides
Draw the following molecules:
a) N-propyl propanamide
O
C
C
C
N
C
C
C
b) N-bromo-N-methyl hexanamide
O
C
C
C
C
C
C
N
C
Br
c) N,N-dimethyl pentanamide
O
C
C
C
C
C
N
C
C
d) 3,N-dimethyl-N-propyl butanamide
O
C
C
C
C
C
N
C
C
e) ethyl-N-methyl butanamide
O
C
C
C
C
C
C
N
C
C
C
Name the following compounds:
10.
O
1.
H3C CH2
C O CH3
methyl propanoate
1-propoxypentane
2.
H3C
11.
Br
O
CH CH2
C
O
OH
3-ethylhexan-2-one
3-bromobutanoic acid
3.
O
12.
O
H3C C
Cl
H3C C CH2 CH3
C CH3
Br
cis-2-bromo-3-chlorobut-2-ene
butanone
4.
H3C CH
13.
CH2 OH
O
H3C CH2
C N CH2
Cl
Cl
2-chloropropan-1-ol
5.
N,N-chloroethyl propanamide
O
H3C C C CH2
14.
CH
H3C CH2
CH2
pent-3-ynal
6.
CH3
O
CH2
CH3
O
CH3
15.
CH3
H3C C O
CH
CH2
CH3
H3C
N-methyl-2-methyl-2-aminobutane
2-butyl ethanoate
7.
16.
O
O
OH
2-ethylpentanal
H3C CH CH2 CH
CH3
H2C
CH2
CH3
CH2
CH2
H3C
CH2
4-ethyl-2-methylnonane
9.
CH
2-ethoxypentane
HN CH3
H3C C CH2
8.
CH3
OH
H3C C
3-methylhexanoic acid
17.
Cl
H3C CH
C C CH2
O
CH
CH3 OH
trans-3-chloro-4-hydroxy-5-methylhex-3-enal
CH3
CH3
2-methylpropan-2-ol
Comparing Organic Compounds
Draw the following 5 molecules and place them in order of highest boiling point to lowest
boiling point. Research their boiling points and confirm your answers. Explain your
reasoning fully:
a) pentan-1-ol
(138 °C)
d) pentan-2-one
H3C
H3C
CH2
CH2
e) pentanal
CH2
CH2
b) 2-methylbutan-2-ol
O
CH
c) 1-ethoxypropane
H3C
O
CH2
C
CH3
(103 °C)
CH2
O
CH2
OH
H3C
H3C
CH2
CH2
CH2
(110 °C)
CH2
CH2
C
(102 °C)
CH3
HO
CH3
(64 °C)
CH2
CH2
CH3
Draw the following 7 molecules and place them in order of highest boiling point to lowest
boiling point. Explain your reasoning:
c) hexanoic acid (204 °C)
a) hexan-3-ol
(135 °C)
OH
O
CH2
CH2
C
H3C
OH
CH2
CH2
H3C
d) hexan-3-one
e) 1-propyl propanoate (123 °C)
(123 °C)
CH
CH2
CH2
CH2
O
O
H3C
C
CH2
H3C
CH2
CH2
CH2
CH3
CH
CH2
CH2
CH2
H3C
CH2
f) 2-methylpentane
H3C
CH2
b) 1-methoxy-2-methylbutane (81 °C)
NH2
CH2
CH3
C
O
CH2
CH3
g) 3-aminohexane (115 °C)
H3C
CH3
CH3
(69 °C)
CH3
CH
CH3
O
CH
CH2
CH2
CH3
Organic Reactions Worksheet
Note – Use HCl, H2O, OA such as FeO, CuO, KMnO4,etc. and NH3,, Cl2 when necessary
1. Using an alkene, produce butan-2-one
Need: 2° alcohol; butan-2-ol
C C C C
+
H2O
C C C C
OH
but-1-ene
butan-2-ol
addition
O
C C C C
+
FeO
+
C C C C
H2O
+
Fe
OH
butan-2-ol
butanone
oxidation
2. Using two alcohols, produce methyl butanoate
Need: methanol and butanoic acid
Create the carboxylic acid:
O
C C C C OH
+
CuO
butan-1-ol
C C C C
+
H2O
butanal
O
C C C C
+
Cu
oxidation
O
+
CuO
butanal
C C C C OH
+
butanoic acid
H2O
+
Cu
oxidation
Create the ester:
O
C C C C OH
butanoic acid
O
+
HO C
C C C C O C
methyl butanoate
+
Cu
condensation
3. Using an alkane and an carboxylic acid, produce N-ethyl butanamide
Need: aminoethane and butanoic acid
Create the amine:
+
C C
Cl
Cl
+
C C Cl
ethane
HCl
1-chloroethane
+
C C Cl
NH3
substitution
+
N C C
1-chloroethane
HCl
aminoethane
substitution
Create the amide:
O
O
C C C C OH
+
N C C
butanoic acid
C C C C N C C
aminoethane
+
H2O
N-ethyl butanamide condensation
4. Using an alkane and an alkene, produce methoxyethane
Need: aminoethane and butanoic acid
Create an alcohol from the alkane:
C
+
Cl
Cl
methane
C Cl
+
C Cl
HCl
chloromethane
+
H2O
chloromethane
C OH
+
substitution
HCl
methanol
substitution
Create an alcohol from the alkene:
C C
+
H2O
ethane
C C OH
ethanol
addition
Create the ether:
C OH
methanol
+
C O C C
HO C C
ethanol
methoxyethane
+
H2O
condensation
5. Using an alcohol and an haloalkane, produce ethyl propanoate
Need: ethanol and propanoic acid
Create the carboxylic acid from the alcohol:
+
C C C OH
MnO2
O
C C C
propan-1-ol
O
+
H2O
+
propanal
O
+
C C C
MnO
C C C OH
propanal
MnO
oxidation
+
Mn
propanoic acid
oxidation
Create the alcohol from the haloalkane:
+
C C Cl
H2O
C C OH
chloroethane
+
HCl
ethanol
Create the ester:
O
substitution
O
+
C C C OH
propanoic acid
HO C C
C C C O C C
ethanol
ethyl propanoate
+
H2O
condensation
6. Using an alcohol, produce an aminoethane
Need: ethanol
Create an alkene from the alcohol:
H2SO4
C C OH
ethanol
C C
+
H2O
ethene
elimination
Create the haloalkane:
C C
ethene
+
HCl
C C Cl
chloroethane
substitution
C C Cl
+
NH3
C C N
chloroethane
+
HCl
aminoethane
substitution
7. Using an alkene, produce pentan-2-one
Need: pentan-2-ol
+
C C C C C
H2O
C C C C C
OH
pentan-2-ol
pent-1-ene
addition
O
C C C C C
+
ZnO
C C C C C
+
H2O
+
OH
pentan-2-ol
pentan-2-one
oxidation
Zn
ALIPHATIC HYDROCARBON ASSIGNMENT
1.
(a) Look up the boiling points for the alkanes, methane through decane.
C1 -164°C
C5 31°C
C9 151°C
C2 -89°C
C6
69°C
C10 174°C
C3
C7
-42°C
98°C
C4
C8
-0°C
126°C
(b) Explain the trend in their boiling points.
As the C chain length increases, the number of electrons increase and the London
Dispersion Force increases due to the greater temporary dipoles.
2.
(a) Lookup the boiling points for 2-methyl pentane and 2,2-dimethyl butane.
60.3°C
49.7°C
(b) Draw their structural formulae.
C
C
C
C
C
C
C
C
C
C
C
C
(c) Name their straight chain alkane isomer.
Hexane
(d) Explain the trend in boiling points within this series of isomers.
Branching increases distance of closest approach between molecules and therefore
weakens interparticle forces. Branching decreases magnitude of temporary dipoles
and therefore weakens London Dispersion forces.
3.
Explain why reactions involving alkanes are often quite slow in spite of being
significantly exothermic.
Collision geometry is complex and the mechanism will involve the breakage of
numerous strong covalent bonds. The C’s have a negative oxidation number which
stabilizes the atoms and makes it more difficult to break the strong bonds.
4.
Construct models, give structural formulae and condensed formulae and IUPAC names
for as many isomers of C6H12 as possible. Use straight chain branches only.
Answers variable and would include
C
C
C
C
C
C
C
C
C
C
C
CH2CHCH2CH2CH2CH3
hexene
CH3CHCHCH2CH2CH3
2-hexene
CH3CHC(CH3)CH2CH3
3-methyl-2-pentene
C
C
C
6.
C
C
C
C
Give structural and projection formulae for the geometric isomers of 3-hexene.
H
H
C
H
H
H
H
H
C
H
C
C
H
C
C
H
H
H
H
C
H
H
H
C
C
H
H
TRANS
Using structural formulae, illustrate the following reactions
(a) propane + chlorine
(b) but-1-yne + oxygen
(c) but-1-ene + hydrochloric acid
C
C
C
C
H
C
H
CIS
7.
H
C
+ HCl
C
C
Cl
C
C
H
C
H
H
SOME FUNCTIONAL GROUPS AND THEIR REACTIVITY
1.
List the functional groups for the following classes of compounds; alcohols, ethers
aldahydes, ketones, carboxylic acids, esters, amines and amides.
Common groups of atoms which result in common properties and allow
classification of compounds into groups with similar properties.
2.
For each of the following sets of compounds and their boiling points
(ii) Name the compounds and (ii) Explain the trend in boiling point.
(a) CH4 (-164 °C)
methane
HCHO (-21 °C)
CH3OH (65 °C)
HCO2H (101 °C)
methanal
methanol
methanoic acid
London dispersion, dipole-dipole, H-bonding, stronger H-bonding due to degree of
polarity
(b) CH3OH (65 °C)
methanol
C2H5OH (79 °C)
C3H7OH (98 °C)
ethanol
propan-1-ol
Larger molecules with more electrons, result in larger London dispersion and dipoledipole forces
(c) C2H6 (-89 °C)
ethane
CH3OCH3 (-25 °C)
C2H5OC2H5 (35 °C)
methoxymethane
ethoxyethane
London dispersion, slight dipole-dipole and London dispersion forces, slightly larger
dipole-dipole and dispersion forces due to greater size and number of electrons.
(d) C3H8 (-42 °C)
propane
CH3COCH3 (56 °C)
C2H5COC2H5 (102 °C)
propanone
pentan-3-one
London dispersion, dipole-dipole, dipole-dipole with larger London dispersion
forces due to greater size and more electrons.
(e) CH3CO2H (118 °C)
ethanoic acid
C2H5CO2H (141 °C)
C3H7CO2H (164 °C)
propanoic acid
butanoic acid
Stronger H-bonding & increasing London dispersion forces due to greater size and
number of electrons
(f) CH3CO2CH3 (57 °C)
methyl ethanoate
C2H5CO2C2H5 (99 °C)
ethyl propanoate
Increasing dipole-dipole and London dispersion forces due to greater size and
number of electrons.
3.
H
H
Give the structural diagrams, condensed formulae and the names for the primary,
secondary and tertiary isomers of C6H13OH.
H
H
H
H
H
H
C
C
C
C
C
C
H
H
H
H
H
H
H
H
H
H
H
H
C
C
C
C
C
C
H
H
H
H
OH H
O
H
CH3-CH2-CH2-CH2-CH2-CH2-OH
hexan-1-ol
H
CH3-CH2-CH2-CH2-CH(OH)-CH3
hexan-2-ol
H
H
H
4.
C
H
H
H
H
H
C
C
C
C
H
H
H
OH H
C
H
CH3-CH2-CH2-C(CH3)(OH)-CH3
2 methylpentan-2-ol
Using an alcohol with a two carbon main chain, illustrate end explain the differences in
oxidation of primary, secondary and tertiary alcohols. In each case, name the product of
the reaction and use oxidation numbers to confirm that oxidation has occurred.
Primary:
-
O
MnO 4
C
C
+
OH
C
C
+ 2H
H
-1
+1
ethanol
ethanol
O
C
C
O
+
C
H
+1
ethanal
-
MnO 4
C
+ 2H
OH
+3
ethanoic acid
+2 e
+2 e
Secondary:
C
C
-
O
C
C
MnO 4
+
C
C
C
+ 2e
O
H
C
+ 2H
0
+2
propanone
propan-2-ol
Tertiary: No further oxidation due to the lack of any remaining hydrogen atoms on the
functional group carbon.
5.
Illustrate using structural formulae and balanced equations, each of the following. Name
all products and types of reaction.
(a) methanoic acid + water
H
H
H
C OH
+
H
H2O
H
C O
-
+
H3O+
H
(b) 2-methylbutanoic acid + sodium carbonate
O
H H H
H C C
+
C OH
C
O
H H H
Na2CO3
H C C
H H CH
3
C
C O Na
+
+ H2O
CO2
H H CH
3
(c) ethanoic acid + propan-1-ol
C
O
H+
O
+ H
C
O
C
C
C
C
C
O
C
C
+ H2 O
C
OH
(d) propyl ethanoate + sulfuric acid
O
C
C
O
H2 SO4
O
C
C
C
+ H2 O
C
+
C
OH
H
O
C
C
C