b.

REVIEW TIME

Exercise1
1. Briefly identify the important distinctions between an
alkane and an alkyl group.
8. What is a substituent? How is the location of a
2. How many carbon atoms are present in each substituent indicated in the IUPAC system?
molecule?
9. Briefly identify the important distinctions between a
a. 2-methylbutane common name and an IUPAC name.
b. 3-ethylpentane
3. How many carbon atoms are present in each Answer1
molecule? 1. An alkane is a molecule; an alkyl group is not an
a. 2,3-dimethylbutane independent molecule but rather a part of a molecule that we
consider as a unit.
b. 3-ethyl-2-methylheptane
 
4. Draw the structure for each compound.
3.
a. 3-methylpentane
a. 6
b. 2,2,5-trimethylhexane
b. 10
c. 4-ethyl-3-methyloctane
 
5. Draw the structure for each compound.
5.
a. 2-methylpentane
a.
b. 4-ethyl-2-methylhexane
c. 2,2,3,3-tetramethylbutane
6. Name each compound according to the IUPAC
system.
a.
  
b.

b.

c.
7. Name each compound according to the IUPAC
system.  
a. 7.
a. 2,2,4,4-tetramethylpentane
b. 3-ethylhexane
 
9. Common names are widely used but not very systematic;
IUPAC names identify a parent compound and name other
groups as substituents.
exercise2
1. Without referring to a table, predict which has a higher
boiling point—hexane or octane. Explain.
2. If 25 mL of hexane were added to 100 mL of water in
a beaker, which of the following would you expect to
happen? Explain.
a. Hexane would dissolve in water.
b. octane (a typical hydrocarbon in gasoline).
8. The density of a gasoline sample is 0.690 g/mL. On
the basis of the complete combustion of octane,
calculate the amount in grams of carbon dioxide (CO2)
and water (H2O) formed per gallon (3.78 L) of the
gasoline when used in an automobile.
9. Draw the structures for the five isomeric hexanes
(C6H14). Name each by the IUPAC system.

b. Hexane would not dissolve in water and would float 10. Indicate whether the structures in each set represent
on top. the same compound or isomers.

c. Hexane would not dissolve in water and would sink a.

to the bottom of the container.
3, Which halogen reacts most readily with alkanes? Which
reacts least readily?
b.

Answer2
1. octane because of its greater molar mass
2. b; hexane is insoluble in water and less dense than
water.
c.
`3. most readily: F2; least readily: I2

Exercise3
1. You find an unlabeled jar containing a solid that melts 11. Consider the line-angle formulas shown here and
at 48°C. It ignites readily and burns readily. The answer the questions.
substance is insoluble in water and floats on the
surface. Is the substance likely to be organic or
inorganic?
2. Give the molecular formulas for methylcyclopentane,
2-methylpentane, and cyclohexane. Which are
isomers?
3. What is wrong with each name? (Hint: first write the
structure as if it were correct.) Give the correct name
for each compound.
a. 2-dimethylpropane
b. 2,3,3-trimethylbutane a. Which pair of formulas represents isomers? Draw
each structure.
c. 2,4-diethylpentane
d. 3,4-dimethyl-5-propylhexane b. Which formula represents an alkyl halide? Name
the compound and write its condensed structural
4. What is the danger in swallowing a liquid alkane? formula.
5. Distinguish between lighter and heavier liquid alkanes
in terms of their effects on the skin. c. Which formula represents a cyclic alkane? Name
the compound and draw its structure.
6. Following is the line formula for an alkane. Draw its
structure and give its name. d. What is the molecular formula of the compound
represented by (i)?

Answer3
1. organic
7. Write equations for the complete combustion of each
 3.
compound.
a. Two numbers are needed to indicate two
a. propane (a bottled gas fuel)
substituents; 2,2-dimethylpropane.
 b. The lowest possible numbers were not used; 2,2,3- 2. Classify each compound as a cis isomer, a trans
trimethylbutane. isomer, or neither.
c. An ethyl substituent is not possible on the second a.
carbon atom; 3,5-dimethylheptane.
d. A propyl substituent is not possible on the fifth
carbon atom; 3,4,5-trimethyloctane.
 5. Lighter alkanes wash away protective skin oils; heavier
alkanes form a protective layer.
 
 7.
b.
a. C3H8 + 5O2 → 3CO2 + 4H2O
b. 2C8H18 + 25O2 → 16CO2 + 18H2O
 
9. CH3CH2CH2CH2CH2CH3; hexane

 
c.

 
d.

 
11. Answer4
a. ii and iii; CH3CH2CH2CH2CH2CH2CH3 and 1. Cis-trans isomers are compounds that have different
configurations (groups permanently in different places
in space) because of the presence of a rigid structure
in their molecule. Alkenes and cyclic compounds can
exhibit cis-trans isomerism.
2.  
b. iv; 3-chloropentane; CH3CH2CHClCH2CH3
c. i; ethylcyclopentane; a. trans
b. cis
c. cis
d. neither
d. C7H14

Key Takeaway
Exercise4  Cis-trans (geometric) isomerism exists when there is
1. What are cis-trans (geometric) isomers? What two restricted rotation in a molecule and there are two
types of compounds can exhibit cis-trans isomerism?
 nonidentical groups on each doubly bonded carbon
atom.
Solution
1. Ten carbon atoms in the LCC makes the compound a
derivative of decane (rule 1), and the OH on the third
Exercise5 carbon atom makes it a 3-decanol (rule 2).

1. Draw the structures of the cis-trans isomers for each

compound. Label them cis and trans. If no cis-trans
isomers exist, write none.
a. 2-bromopent-2-ene
b. hept-3-ene
c. 4-methylpent-2-ene The carbon atoms are numbered from the end closest
to the OH group. That fixes the two methyl (CH3)
d. 1,1-dibromobut-1-ene
groups at the sixth and eighth positions. The name is
e. but-2-enoic acid (CH3CH=CHCOOH) 6,8-dimethyldecan-3-ol (not 3,5-dimethyl-8-decanol).
2. Five carbon atoms in the LCC make the compound a
Answer5 derivative of pentane. Two OH groups on the first and
fifth carbon atoms make the compound a diol and give
the name pentane-1,5-diol (rule 3).
1.  
a.

 
Exercise6
b.
1. Name each alcohol and classify it as primary, secondary, or
tertiary.
a.     CH3CH2CH2CH2CH2CH2OH
 
b.

 c.       none
d.       none
e.

 
c.

Example 1
Give the IUPAC name for each compound.
 
1.

2. Name each alcohol and classify it as primary, secondary, or

2. HOCH2CH2CH2CH2CH2OH tertiary.
 a.

b.
 
 
b.

c.

Exercise7
  1. Why is ethanol more soluble in water than 1-hexanol?
2. Why does 1-butanol have a lower boiling point than 1-
hexanol?

Answer7
c.
1. Ethanol has an OH group and only 2 carbon atoms; 1-
  hexanol has one OH group for 6 carbon atoms and is
thus more like a (nonpolar) hydrocarbon than ethanol
3. Draw the structure for each alcohol. is.
a. hexan-1-ol 2. The molar mass of 1-hexanol is greater than that of 1-
butanol.
b. 3,3-dimethylbutan-2-ol
c. cyclobutanol
Exercise8
 
1. Name each compound.
4. Draw the structure for each alcohol.
a. cyclopentanol
b. 4-methylhexan-2-ol
c. 4,5-dimethylheptan-3-ol

Answer6
a.
1.
 
a. hexan-1-ol; primary
b.
b. hexan-3-ol; secondary
c. 3,3-dibromo-2-methylbutan-2-ol; tertiary
 
3.

 
2. Name each compound.
a.
 
 2. Which is more soluble in water—ethyl methyl ether
(CH3CH2OCH3) or 1-butanol (CH3CH2CH2CH2OH)?
Explain.

Answer9
1. Diethyl ether has no intermolecular hydrogen bonding
a. because there is no OH group; 1-butanol has an OH
and engages in intermolecular hydrogen bonding.
 
2. Ethyl methyl ether (three carbon atoms, one oxygen
atom) is more soluble in water than 1-butanol (four
carbon atoms, one oxygen atom), even though both
can engage in hydrogen bonding with water.

b.
Key Takeaways
   To give ethers common names, simply name the
3. Draw the structure for each compound. groups attached to the oxygen atom, followed by the
generic name ether. If both groups are the same, the
a. m-iodophenol group name should be preceded by the prefix di-.
 Ether molecules have no OH group and thus no
b. p-methylphenol (p-cresol) intermolecular hydrogen bonding. Ethers therefore
  have quite low boiling points for a given molar mass.
 Ether molecules have an oxygen atom and can
4. Draw the structure for each compound. engage in hydrogen bonding with water molecules. An
ether molecule has about the same solubility in water
a. 2,4,6-trinitrophenol (picric acid) as the alcohol that is isomeric with it.
b. 3,5-diethylphenol

Answer8
1.
a. o-nitrophenol Exercise10
b. p-bromophenol 1. How can ethanol give two different products when heated
with sulfuric acid? Name these products.
 
2. Which of these ethers is isomeric with ethanol—
3. CH3CH2OCH2CH3, CH3OCH2CH3, or CH3OCHS3?
3. Name each compound.
a.           CH3OCH2CH2CH3
b.

a.
 

 
4. GIVE THE COMMON Name each compound.
b. a. CH3CH2CH2CH2OCH3
b. CH3CH2OCH2CH2CH3
Exercise9  
1. Why does diethyl ether (CH3CH2OCH2CH3) have a
5. Draw the structure for each compound.
much lower boiling point than 1-butanol
(CH3CH2CH2CH2OH)? a. methyl ethyl ether
 b. tert-butyl ethyl ether
 
6. Draw the structure for each compound.
a. diisopropyl ether
b. cyclopropyl propyl ether

Answer10
1. Intramolecular (both the H and the OH come from the same
molecule) dehydration gives ethylene; intermolecular (the H
comes from one molecule and the OH comes from another
molecule) dehydration gives diethyl ether.
 
3.
a. methyl propyl ether
b. ethyl isopropyl ether
 
5.
a.                    CH3OCH2CH3
 

b.