Download SCH4UOrganicWS - SCH4U1-CCVI

ALKANES
1. Draw structural formula for:
a) 2,2,4-trimethylpentane
b) 3,4-diethylheptane
c) 3-methylheptane
d) 4-ethyl-3-methylheptane
e) 3-chloro-2-methylhexane
f) 2-chloro-2-methylpentane
g) 4-bromo-5-iodo-2,2,3-trimethylhexane
h) 5,6-dichloro-3-ethyl-2,3-dimethyloctane
2. Draw and name 3 isomers of C5H12.
3. Which compound has the higher melting point: propane or pentane? Explain.
4. Name the following:
a)
CH3
CH3
CH
CH3
CH2
C CH3
CH3
b)
c)
CH3
CH2
CH
CH
CH2
CH3
CH2 CH2 CH3
CH2
CH3
CH3 CH2 CH2 CH2 CH CH3
CH3 CH2
d)
CH3
CH2
CH
CH
CH2
CH2
CH2
CH3
CH3 CH2 CH3
Cl
e)
CH3
CH
CH
CH2
CH2
CH3
CH3
Cl
f)
CH3
C CH2
CH2
CH3
CH3
g)
CH3 CH3 Br
CH3
C
CH
CH
CH3
CH3
CH
CH3
I
CH3 CH2
h)
CH
C
CH3 CH3
Cl
CH2
CH
CH
Cl
CH2
CH3
ALKENES
1. Draw structural formula for the following:
a) 2-methylpropene
b) trans-2,3-dibromobut-2-ene
c) cis-hex-3-ene
d) 2-ethylpent-1-ene
e) cis-4-chloro-5-methylhex-2-ene
f) 4,4-dimethylhex-1-ene
g) trans-3-bromo-2-iodo-4,5,5-trimethylhex-2-ene
ene
h) trans-3,4-dichloro-6-ethyl-6,7-dimethyloct-3-
2. a) Draw and name the geometric isomers of C2H2Cl2.
b) Which of the two compounds above has the higher melting point? Explain.
3. Name the following:
a)
CH3
C
CH2
CH3
b)
Br
CH3
C
C
CH3
c)
CH3
Br
CH2
C
C
H
H
CH2
CH3
CH2
d)
CH3
CH2
C
CH2
CH2
CH3
Cl
e)
CH3
CH
CH
C
H
C
H
CH
CH2
CH3
f)
CH3
CH2 CH3
CH3
C
CH2
CH3
g)
H3C
CH3 CH3
Br
C
C
CH
CH3
h)
CH3
C
CH3
I
CH3
CH2
CH
C
CH3
CH3
Cl
CH2
C
C
Cl
CH2
CH3
ALKYNES
1. Draw structural formula for the following:
a) 4,5-dimethylhept-2-yne
b) 3,3-dimethylbut-1-yne
c) 4-methylpent-2-yne
d) 4-ethylhex-2-yne
e) 4-chloro-5-methylhex-2-yne
f) 5,5-dimethylhept-1-yne
g) 1-iodo-3,4,4-trimethylpent-1-yne
h) 6-ethyl-6,7-dimethyloct-3-yne
2. a) Draw and name the isomers of C4H5Cl.
b) Which of the isomer compounds above has the higher melting point? Explain.
3. Name the following:
a)
CH3
C
C
CH
CH
CH3
CH3
CH2
CH3
CH3
b)
HC
C
C
CH3
CH3
CH3
c)
CH3
C
C
CH
d)
CH3
CH2
CH3
CH2
CH3
CH
C
C
CH3
Cl
e)
CH3
CH
CH
C
C
CH3
CH3
CH2
f)
CH3
C
CH3
CH2
CH2
C
CH
CH3
CH3 CH3
g)
CH3
C
CH
C
C
I
CH3
h)
CH3
CH3
CH2
CH
C
CH3
CH3
CH2
C
C
CH2
CH3
Nomenclature for Alcohols
Draw the following molecules:
a). 2-chlorobutan-2-ol
b) 2-methylheptan-2-ol
c) octane-1,4-diol
d) cyclopentanol
e) 2,3,4-trichloro-5-methylundecan-1-ol
Name the following structures (left to right, top to bottom):
CH2
HO
Cl
CH3
CH
CH
CH
CH
Cl
Cl
CH2
CH2
CH2
CH2
C
C
CH2
OH
OH
C
CH3
HO
C
CH2
CH
CH2
C
OH
CH2
H3C
CH3
CH2
CH2
CH2
CH2
C
Cl
CH3
C
C
C
C
C
C
C
OH
C
Nomenclature for Ethers
Draw the following molecules:
a) 1-chloro-1-ethoxypropane
b) 2-methyl-1-propoxyoctane
c) 1-propoxypropane
d) 2-methoxypropane
e) 7-methyoxyoctan-2-ol
Name the following structures (from left to right, top to bottom):
CH2
C
C
O
C
H3C
O
CH2
CH2
CH2
CH3
C
CH2
O
CH2
H2C
CH2
CH2
CH
H3C
CH2
CH2
CH2
CH3
CH3
CH3
C
C
Cl
O
C
C
C
H3C
CH2
CH
OH
CH2
CH2
CH
CH2
O
CH3
Nomenclature for Aldehydes
Draw the following molecules:
a) 3,3-dimethylbutanal
b) 4-bromo-3-chloro-5-ethyl-2-methylheptanal
c) 2-bromo-3-ethylhexanal
d) 4-chloropentanal
e) 2,2,4-trichlorooctanal
Name the following structures (left to right, top to bottom):
O
Cl
Cl
CH
C
C
C
C
C
O
C
CH2
Cl
Cl
CH2
H3C
Br
CH3
CH
CH
CH
CH
CH2
Cl
CH
CH2
CH2
CH3
CH2
O
CH
H3C
O
C
CH
CH2
CH3
C
C
C
C
C
H3C
C
CH3
Br
O
C
C
Nomenclature for Ketones
Draw the following molecules:
a) 3-chloro-4-phenylpentan-2-one
b) 3-bromohexan-2-one
c) 3-ethyl-2,5,7-trimethyloctan-4-one
d) 2,2-dimethyldecan-4-one
e) 1,3,5-trichlorohexane-2,4-dione
Name the following structures (left to right, top to bottom):
O
C
C
CH3
H3C
Cl
C
Cl
C
C
C
O
C
CH2 CH2
Cl
O
H3C
CH2
CH2
C
CH3
CH2 CH2
CH3
H3C
HC
C
CH3
CH3
CH2 CH3
CH2 HC
HC
HC
CH3
Cl
H3C
O
C
C
CH
CH
O
C
C
Br
C
C
C
O
CH3
Nomenclature for Carboxylic Acids
Draw the following molecules:
a) 3-fluoropentanoic acid
b) 2,2-dimethylbutanoic acid
c) 2,3,3,5-tetrachlorooctanoic acid
d) trans-4,4-dimethylhex-2-enoic acid
e) propanedioic acid
Name the following structures (from left to right, top to bottom):
O
HO
Cl
C
C
C
C
Cl
Cl
C
C
C
C
Cl
O
O
C
C
C
C
C
OH
HO
C
O
C
C
OH
F
C
C
C
O
C
C
C
C
OH
C
C
C
C
O
C
C
C
OH
Nomenclature for Esters
Draw the following molecules:
a) 1-butyl ethanoate
b) 2-butyl propanoate
c) 3-pentyl 2-methylbutanoate
d) 3-methylbutyl propanoate
e) dichloromethyl ethanoate
Name the following structures (from left to right, top to bottom):
O
O
C
C
C
O
C
C
C
C
C
C
O
C
C
C
C
C
O
O
C
C
C
C
O
C
C
C
O
C
C
C
C
C
O
C
C
C
C
C
C
Cl
O
C
Cl
C
Nomenclature for Amines
Draw the following molecules:
a) N-ethyl-1-aminopropane
b) 2-aminohex-1-ene
c) 4-chloro-2-aminoheptane
d) N-ethyl-N-methyl-2-aminobutane
e) N-methylaminomethane
Name the following structures (from left to right, top to bottom):
N
C
C
C
C
C
C
C
C
N
C
C
C
Cl
C
N
C
C
C
C
C
C
C
N
C
C
C
C
N
C
C
C
C
Nomenclature for Amides
Draw the following molecules:
a) N-propyl propanamide
b) N-bromo-N-methyl hexanamide
c) N,N-dimethyl pentanamide
d) 3,N-dimethyl-N-propyl butanamide
e) 2-ethyl-N-methyl butanamide
Name the following structures (from left to right, top to bottom):
O
C
C
C
C
C
C
O
N
C
C
C
C
Br
C
N
C
C
C
O
C
C
C
N
C
C
C
O
C
C
C
O
C
C
C
C
C
N
C
C
C
C
N
C
C
C
C
Name the following compounds:
10.
O
1.
H3C
Br
O
CH CH2
C
OH
O
H3C CH2
C O CH3
11.
2.
O
O
H3C CH
12.
3.
H3C C CH2 CH3
H3C C
Cl
4.
CH2 OH
13.
Cl
C CH3
Br
O
H3C CH2
C N CH2
CH3
Cl
O
H3C C C CH2
CH
14.
H3C CH2
CH2
CH
CH3
O
CH2
6.
HN CH3
H3C C CH2
5.
CH3
O
CH3
15.
H3C C O
CH
CH2
CH3
H3C
7.
O
16.
H3C CH CH2 CH
CH3
H2C
CH2
CH3
CH2
CH2
H3C
9.
O
OH
8.
CH2
17.
OH
H3C C
Cl
H3C CH
CH3
CH3
C C CH2
CH3 OH
O
CH
CH3
Draw the following compounds:
1. 1-propoxypentane
2. 3-bromobutanoic acid
10. methyl propanoate
11. 3-ethylhexan-2-one
3. butan-2-one
12. cis-2-bromo-3-chlorobut-2-ene
4. 2-chloropropan-1-ol
13. N,N-chloroethyl propanamide
5. pent-3-ynal
14. 2-ethoxypentane
6. N-methyl-2-amino-2-methylbutane
15. 2-butyl ethanoate
7. 2-ethylpentanal
16. 3-methylhexanoic acid
8. 4-ethyl-2-methylnonane
17. trans-3-chloro-4-hydroxy-5-methylhex-3-enal
9. 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
b) 2-methylbutan-2-ol
c) 1-ethoxypropane
d) pentan-2-one
e) pentanal
Draw the following 7 molecules and place them in order of highest boiling point to lowest
boiling point. Explain your reasoning:
a) hexan-3-ol
b) 1-methoxy-2-methylbutane
c) hexanoic acid
d) hexan-3-one
e) propyl propanoate
f) 2-methylpentane
g) 3-aminohexane
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
2. Using two alcohols, produce methyl butanoate
3. Using an alkane and an carboxylic acid, produce N-ethyl butanamide
4. Using an alkane and an alkene, produce methoxyethane
5. Using an alcohol and an haloalkane, produce ethyl propanoate
6. Using an alcohol, produce an aminoethane
7. Using an alkene, produce pentan-2-one
ALIPHATIC HYDROCARBON ASSIGNMENT
1.
(a) Look up the boiling points for the alkanes, methane through decane.
(b) Explain the trend in their boiling points.
2.
(a) Lookup the boiling points for 2-methyl pentane and 2,2-dimethyl butane.
(b) Draw their structural formulae.
(c) Name their straight chain alkane isomer.
(d) Explain the trend in boiling points within this series of isomers.
3.
Explain why reactions involving alkanes are often quite slow in spite of being
significantly exothermic.
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.
6.
Give structural and projection formulae for the geometric isomers of 3-hexene.
7.
Using structural formulae, illustrate the following reactions
(a) propane + chlorine
(b) but-1-yne + oxygen
(c) but-1-ene + hydrochloric acid
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.
2.
For each of the following sets of compounds and their boiling points
(i) Name the compounds.
(a) CH4 (-164 °C)
HCHO (-21 °C)
CH3OH (65 °C) HCO2H (101 °C)
(b) CH3OH (65 °C)
C2H5OH (79 °C)
C3H7OH (98 °C)
(c) C2H6 (-89 °C)
CH3OCH3 (-25 °C)
C2H5OC2H5 (35 °C)
(d) C3H8 (-42 °C)
CH3COCH3 (56 °C)
C2H5COC2H5 (102 °C)
(e) CH3CO2H (118 °C)
C2H5CO2H (141 °C)
C3H7CO2H (164 °C)
(f) CH3CO2CH3 (57 °C)
C2H5CO2C2H5 (99 °C)
(ii) Explain the trend in boiling point.
3.
Give the structural diagrams, condensed formulae and the names for the primary,
secondary and tertiary isomers of C6H13OH.
4.
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.
5.
Illustrate using structural formulae and balanced equations, each of the following. Name
all products and types of reaction.
(a) methanoic acid + water
(b) 2-methylbutanoic acid + sodium carbonate
(c) ethanoic acid + propan-1-ol
(d) propyl ethanoate + sulfuric acid