CHM096-Tutorial 1 (Alkanes & Alkenes)

CHM 096
TUTORIAL 4
Feb 2013
ALKANES
1.
a)
Write the general formula for alkanes
b)
Why are alkanes referred to as saturated hydrocarbons?
c)Give the name and molecular formula for an alkane that has
i)
6 carbon atoms
ii)
9 carbon atoms
2.
Write the condensed structural formulas and skeletal formulas for:

a)
H
|
HC
|
H
b)
H
|
HC
|
H
3.
H
H
H
|
|
|
C
CCH
|
|
|
H C H H
H
|
H
H
|
H C H H
H H
|
|
|
|
C
C C C H
|
|
|
|
H C H H
H H
|
H
What are the IUPAC names of the following alkanes or its derivatives?
a)
b)
c)
d)
e)
CH3CH2CH2CH3
CH3CHCH2CH3
Cl
CH3CHCHCH3
Cl CH2CH3
CH3CHCH2CH2CH2Br
CH2CH3
CH3CHCH2CH2CHCH2CH3
CH3
CH2CH3
4.
Write all possible structural isomers (including cycloalkane) that have the same molecular formula of C 6H14
5.
Write full structural formulas for:

a)
b)
c)
d)
3-bromopentane
3-ethylhexane
2,2,3-trimethylheptane
1-bromo-2-chlorobutane
6.
Give the IUPAC name and the common name for the compound with the skeletal formula of:
7.
For the formula:

CH3CH(CH3)CH2CH3
Identify the carbon atoms as primary (1o), secondary (2o) or tertiary (3o).
8.
Write a balanced equation for the complete combustion of nonane in excess of oxygen.
9.
Draw structural formulas and give IUPAC names for all the isomers of trichloropropanes (C 3H5Cl3).
10.
Give the names and structures of all compounds which are isomeric with 2,2-dimethylpentane.
11.
What do you understand by the terms:

a)
b)
c)
12.
Aromatic hydrocarbons?
Aliphatic hydrocarbons?
Homologous series?
How many secondary carbons are there in the molecule shown below? What is its molecular formula?
CH3
13.
CH2CH3
The reaction between ethane and chlorine produces nine substituted products.
a)
b)
Write the structural formulas of these products.

Briefly describe the mechanism of free radical substitution reaction that leads to the formation of:
i) a monosubstituted chloroethane
ii) two disubstituted chloroethanes
14.
Which of the following molecules is an alkane? Which could be a cycloalkane?

a)
b)
c)
d)
C2H4
C5H10
C12H26
C7H8
15.
Draw and name the three (aromatic) isomers of C 6H3Cl3.
16.
Cl2 and CH4 react in the presence of sunlight. Which of the following represents the propagation step?
A.
Cl2 + H HCl + Cl
B.
Cl + CH4 CH3Cl + H
C.
Cl + CH4 CH3 + HCl
D.
CH3 + CH3 C2H6
Prepared by: Ho Chong Yuen
ALKENES AND ALKYNES

17.
a)
b)
18.
Give the IUPAC name for:
19.
a)
CH3CH CHCH2Cl
b)
CH2 CHC(CH3)2Cl
c)
CH2CH3
|
H2C CCH2CH3
Write the structural formula and the skeletal formula for each of the following compounds.
a)
b)
c)
d)
20.
Why are alkenes and alkynes called unsaturated hydrocarbons ?

What is the functional group for alkenes?
2,3-dimethyl-2-butane
cis-3-hexene
2-methyl-1-pentene
trans-2,3-dichloro-2-butene
Write equations to show the addition reaction of 2,3-dimethyl-1-butene with:

a)
b)
H2
Cl2
21.
Write equations to show the addition reaction of 2-methyl-2-butene with HCl. Describe the mechanism of
the reaction.
22.
Write the structure of the principal organic product formed in the reaction of 1-pentene with each of the
following:
a)
b)
c)
d)
e)
Hydrogen iodide
Acidified water
Bromine in carbon tetrachloride
aqueous bromine
cold, dilute KMnO4
23.
How would you distinguish between propane and propene by a simple chemical test?
24.
Write the equations for the reactions that occur in the following conversions. State the reagents and
conditions for the reactions.
a)
b)
1-butene 1,2-dibromobutane
1-butene 2-chlorobutane
25.
How would you convert an unsaturated hydrocarbon to a saturated hydrocarbon? Give an example for the
conversion.
26.
A substituted alkene has the molecular formula of C4H7Cl. Its IUPAC name is 4-chloro-1-butene.
a)
b)
c)
27.
Draw the structure for this alkene.

What would be the product formed when C 4H7Cl undergoes hydrogenation?
Write equation for the reaction of C4H7Cl with HCl. Name the product formed.
What are the structural formulas for the following alkynes?
a)
C3H4
b)
28.
Compare the reactions of 1-butene and 1-butyne with the following reagents.
a)
b)
29.
H2 (2 moles)
HBr (1 mole)
How would you convert

a)
b)
c)
30.
C4H6
ethene to ethanol?
ethene to Iodoethane (ethyl iodide)?
2-chloropropane to propene
a)
What is the major product of addition reaction occurred between 3-methyl-1-pentene and HBr?
Name the rule you used in determining the major and minor products.
b)
Explain the mechanism of addition reaction in (a) above that leads to the formation of the major
product.
31.
The hydration of alkenes is an acid catalysed addition reaction that produces alcohol (ROH). What is
the alcohol produced from the hydration of 2,3,4-trimethyl-2-pentene?
32.
An alkene, X, forms an addition product CH 3CH(OH)CH3. What should be the name and the structural
formula of X?
33.
What is the major product in the reaction:

a)
2,2,4-Trimethyl-3-hexene + HI
b)
= CH2
HCl
methylenecyclohexane
34.
How many alkenes produce 2,3-dimethylbutane on catalytic hydrogenation?
35.
Specify the reagents suitable for converting 3-methyl-2-pentene to each of the following compounds.
a)3-chloro-3-methylpentane
b)2,3-dibromo-3-methylpentane
36
Give the IUPAC name of the following compound.
37.
When a gas Y reacts with Z, a mixture of CH2BrCH2Br and CH2BrCH2OH are produced. Y and Z are
probably:
Y
A.
B.
C.
D.
HBr(gas)
ethene
ethene
Br2 vapour
Z
ethene
NaBr solution
bromine water
ethene

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CHM 096

Write the condensed structural formulas and skeletal formulas for:

Write full structural formulas for:

For the formula:

What do you understand by the terms:

Write the structural formulas of these products.

Which of the following molecules is an alkane? Which could be a cycloalkane?

Draw and name the three (aromatic) isomers of C 6H3Cl3.

Cl + CH4 CH3 + HCl

CH3 + CH3 C2H6

Prepared by: Ho Chong Yuen

ALKENES AND ALKYNES

Give the IUPAC name for:

Why are alkenes and alkynes called unsaturated hydrocarbons ?

Write equations to show the addition reaction of 2,3-dimethyl-1-butene with:

Draw the structure for this alkene.

What are the structural formulas for the following alkynes?

How would you convert

What is the major product in the reaction:

How many alkenes produce 2,3-dimethylbutane on catalytic hydrogenation?

Give the IUPAC name of the following compound.

Prepared by: Ho Chong Yuen

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