ALKANES PROBLEMS
1.
Give the IUPAC name and, where possible, the common name of each of the following compounds:
a)
CH2I2
b)
CHBr3
c)
CH3Cl
d)
CH3
CH
CH2
CH2
Cl
CH3
e)
CH3(CH2)4CH3
f)
CI4
CH3
g)
CH3
CH2
C
CH3
CH3
h)
CH3
CH
CH3
Br
i)
CH3
CH
CH2
CH3
F
j)
Cl
Br
k)
CH3CH2I
l)
CH3-CH2-CH2-F
page 1
ALKANES PROBLEMS
2.
Draw line bond structures and structural formulas for each of the following compounds:
a) isobutyl bromide
b) methylene chloride
c) 4-chloro-3-methyloctane
d) 3-methylpentane
e) 3,4,5-tribromooctane
f) 2-bromo-1-chloropropane
g) 2,2-dibromo-3-chloro-4-iodoheptane
h) isobutane
i)
2,2-dibromo-1-chloro-4-(1-methylethyl)nonane
j)
1,1,1-trichlorobutane
k) t-butyl bromide
l)
n-amyl iodide
m) 2,4,6-trimethyldecane
n) 4-ethylnonane
o) chloroform
p) sec-butyl fluoride
q) methylcyclohexane
page 2
ALKANES PROBLEMS
3.
Give the IUPAC name of each of the following compounds:
CH3
a)
CH3
CH2
CH
CH
CH3
CH3
CH3
b)
CH3
CH2
CH2
CH
CH2
CH3
CH
CH2
CH3
CH3
c)
CH3
CH2
CH
CH2
CH2
CH2
CH
CH2
CH2
CH3
CH3
CH3
d)
CH3
C
CH2
CH3
CH2
CH3
Cl
Br
e)
CH3
CH2
CH
CH
CH
CH3
CH3
CH
CH
CH3
Br
4.
Identify each of the carbon atoms in question 3 as being primary, secondary, tertiary, or quaternary.
5.
Draw and name structural formulas of at least 4 isomers of:
a) bromopentane (amyl bromide)
b) fluorobutane
c) diiodocyclohexane
page 3
ALKANES PROBLEMS
6.
Which of the following pairs of structural formulas represent identical compounds and which
represent constitutional (structural) isomers?
a)
CH3
b)
CH2
CH
H3C
CH2
CH3
CH2
H3C
C
CH3
CH2
CH
CH2
7.
CH2
CH2
CH
CH3
CH3
and
CH3
CH3
CH
CH
Br
CH
CH3
Br
CH2
CH3
CH3
CH3 CH2
CH2
c)
and
CH3
CH3
and
CH3
CH3
CH2
CH
CH3
H3C
CH
CH
CH3
CH3
Draw line bond and structural formulas of the following compounds:
a) 4-(1-methylethyl)heptane
b) 2,3-dimethyl-6-(2-methylpropyl)decane
c) 2-methyl-5-(1,2-dimethylpropyl)nonane
d) t-butylcyclopentane
e) 1-sec-butyl-4-isobutylcyclohexane
f) neohexyl bromide
page 4
ALKANES PROBLEMS
8.
Draw line bond structures and structural formulas for each of the following compounds:
a) 2,2,3,3-tetramethylpentane
b) 4-ethyl-2,2-dimethylheptane
c) 1-ethyl-2-methylcyclohexane
d) cyclobutylcycloheptane
e) neopentylcyclopentane
9.
Draw structures of the following compounds. Show the geometry of substitutents using wedges and
dashed bonds:
a) (Z)-1,4-dichloro-1-methylcyclohexane
b) (E)-1,3-diethyl-1-isopropylcyclobutane
c) 4-t-butyl-3-cyclopentylheptane
page 5
ALKANES PROBLEMS
10.
Write IUPAC names for the following compounds. State the geometry when possible, i.e., (E) or (Z)
a)
H
Br
F
H3C
b)
c)
CH3
CH2
CH
CH3
Br
d)
CH3
Cl
11.
CH2
F
Write expanded formulas for and name the following compounds:
a) CH3(CH2)2CH3
b) CH3CH(CH3)CH2CH3
c) CH3CH2C(CH3)3
d) CH3CHClCH2Cl
e) CH2BrCH2Cl
f) CH3CH(CH3)CHClCH3
g) CH2Cl(CH2)2CH(CH3)CH(CH3)2
page 6
ALKANES PROBLEMS
12. The following names are incorrect. Write the correct name for each.
a) 3-methylbutane
b) 4-methylhexane
c) 2,3,3-trimethylbutane
d) 3,3-dichlorobutane
e) 2-ethylpropane
f) 2,2,1-trichloroethane
g) 2,2-diethylbutane
h) 1,4-dimethylcyclopentane
i)
1-chloro-1-methylpropane
j)
1,1,2-trimethylbutane
13. Chlorination of methane at high temperatures gives four different products. Write balanced equations
for the preparation of each and give a common and IUPAC name to each product.
14. State whether the following molecules are the same or different.
a)
F
H
H
H
C
C
C
H
H
H
C
F
H
b)
CH3
CH2
and
CH2F
CH2
CH2
CH2F
H
CH2
CH2
and
Cl CH2 CH(CH3)2
Cl
CH3
c)
CH3
C
CH3
and
(CH3)3C
CH3
CH3
page 7
ALKANES PROBLEMS
15. Draw a Newman projection and sawhorse projection for the C2 to C3 bond in butane in its eclipsed
conformation.
16. Rank the following in order of increasing boiling point (without looking up the true values).
2-methylhexane
heptane
2,2-dimethylpentane
2,2,3-trimethylbutane
17. Label 1, 2, and 3 H’s in the following compounds.
CH3
CH3
H3C
18. Explain why 4 H’s do not exist.
19. Write a balanced equation for the complete combustion (excess O2) of
a)
ethyne (ethylene), i.e., welders fuel, C2H2.
b) ethane
20. Redraw the following structural formulas as line bond structures.
H
HOH2C
CH2
O
CH3
C
CH2
C
CH2
CH
O
OH
C
H
H
H
CH
CH
OH
OH
H
N
C
C
N
C
H
C
N
O
H
page 8
ALKANES PROBLEMS
21.
In each group of 3 structures, 2 are the same compound. Circle the one that is different in each set.
OH
OH
a)
CH3
HO
CH3
H3C
b)
NH2
CH3CHCHCH2CH3
CH3 CH3
CH3CHCHCH2
CH3
CH3
CH3
CHCH
CH3
NH2
NH2
CH2CH2OH
c)
CH3CH2CHCH3
CH3CHCH2
CH3CH2CHCH2CH2OH
CH2CH2OH
CH3
CH3
22. Draw the structures of at least 1 constitutional isomer of each of the following:
O
O
O
23. The following names are incorrect. Give the correct IUPAC name.
a) sec-propyl chloride (give correct common name here)
b) neobutyl bromide (give correct common name here)
c) 2-tert-butylpentane
d) 2-methyl-2-propylhexane
e) 1,5-dimethylpentane
f) 3-cyclohexylbutane
g) 2-dimethylpentane
h) 1,2-chlorobutane
i)
2 methyl propane
page 9
ALKANES PROBLEMS
24. Number the following compounds in order of increasing density, i.e., 1 = lowest.
a) octane
propane
icosane
b) carbon tetrachloride
water
c) methyl iodide
methyl chloride
methyl chloride
decane
methyl bromide
25. Draw and name all possible monochlorination and dichlorination products of cyclopentane. Consider
all geometric isomers.
Cl2
hv
26. The following names are incorrect. Write the correct IUPAC names.
a) 3-ethyl-4-methylpentane
b) 1-cylcopropyl-3,4-dimethylcyclohexane
c) 2,2-diethylbutane
d) 2,2-dimethylcyclopropane
e) 1,3-dimethyl-6-ethylcyclohexane
f) 2-methyl-1,1,1-trichloropropane
27.
a) Write the formula for a 16 carbon unbranched, acyclic alkane and give its IUPAC name.
b) Write the formula for a 9 carbon cycloalkane with 2 fused rings
c) How many H’s are removed from an alkane formula for each ring?
page 10
ALKANES PROBLEMS
28.
a) State the type of compounds called “aliphatics”.
b) Give the alternate name for a ‘structural isomer’.
c) Give the alternate name for a ‘geometric isomer’.
d) In an alkyl group, the C attached to the main chain is called the ………………. or ……………..
e) Give the IUPAC name and formula for a 20 carbon, unbranched, acyclic alkane.
f) Define ‘locant’.
g) List 3 hyphenated prefixes and state whether they are alphabetized or not.
h) List 3 nonhyphenated prefixes that are alphabetized.
i)
List 3 nonhyphenated prefixes that are not alphabetized.
j)
An alternate name for ‘alkyl halide’ is …………………………….. .
k) Give the word meaning ‘anaerobic destructive heating’.
l)
Destructive heating in the presence of oxygen is called …………………… .
m) List 3 types of industrial pyrolysis processes for petroleum and explain the differences.
29. Give the common names the following groups:
CH2
CH
CH3CH2
CH3C
30. List 4 different kinds of organic reactions and illustrate each by writing an equation showing reactants
and products.
a)
b)
c)
d)
page 11
ALKANES PROBLEMS
31. Considering the reaction A-B  ?,
a) write the products of homolytic cleavage
b) write the products of heterolytic cleavage
32. Draw the Lewis symbol of
a) a bromine free radical
b) an oxygen free radical
33. List 2 kinds of radical reactions
a)
b)
34. How many electrons are transferred in each step of
a) a radical reaction?
b) a polar reaction?
35. Give the name of the high energy complex temporarily formed during a chemical reaction.
36. Define activation energy and explain its significance with respect to the rate of a reaction.
37. Write the condensed formula of a 9-carbon cycloalkane with
a) 1 ring
b) 2 fused rings
page 12