Exercises 1099a methyl group as a substituent attached to the longest
chain?
013.Name the following compound by the IUPAC system:
CH 3 CH(CH 3 )CH 2 CH 3. Draw a constitutional isomer of
this compound, and give its correct IUPAC name.
014.Give the IUPAC name of each of the following
compounds.
(a) CH 3 CH 2 CH 2 CH(CH 3 )CH 2 CH 3
(b) CH 3 CH 2 CH(CH 2 CH 3 )CH 2 CH 3
(c) CH 3 CH(CH 2 CH 2 CH 3 )CH 2 CH 3
(d) CH 3 CH 2 CH 2 CH(CH 3 ) 2
(e) CH 3 CH(CH 3 )CH 2 CH 2 CH 3
015.Write structural formulas for the isomeric saturated
hydrocarbons having the molecular formula C 6 H 14.
Which one would have the highest boiling point?
016.Write structural formulas for four constitutional isomers
of C 7 H 14 that contain a cyclopropyl substituent. Name
each by the IUPAC system.
017.Write the structural formula for 2,2-dimethylpropane.
018.Write the IUPAC name for each of the following.
019.Write structural formulas for 1,1,2-trimethylcyclohexane,
isopropylcyclobutane, and sec-butylcyclohexane.
020.(a) How does the general formula for the alkenes differ
from the general formula for the alkanes? (b) Why are
the general formulas identical for alkenes and cycloal-
kanes that contain the same number of carbon atoms?
021.(a) What are cycloalkenes? (b) What is their general for-
mula? (c) Provide the structural formulas and names of
three examples.
022.Describe the bonding at each carbon atom in (a) ethene,
(b) propene, (c) 1-butene, and (d) 2-methyl-2-butene.
023.(a) What are geometric isomers? (b) Why is rotation
around a double bond not possible at room temperature?
(c) What do cisand transmean? (d) Draw structures for
cis- and trans-3-methyl-3-hexene. How should their melt-
ing and boiling points compare?
024.How do carbon–carbon single bond lengths and carbon–
carbon double bond lengths compare? Why?
025.(a) What are alkynes? (b) What other name is used to
describe them? (c) What is the general formula for
alkynes? (d) How does the general formula for alkynes
compare with the general formula for cycloalkenes?
Why?
026.Describe the bonding and geometry associated with the
triple bond of alkynes.
*027.Write the structural formulas of the following
compounds: (a) 1-butyne; (b) 2-methylpropene;
(c) 2-ethyl-3-methyl-1-butene; (d) 3-methyl-1-butyne.
CH 3CH 3CH 3CH 3CH 3CH 3(a) (b) (c)*028.Write the structural formulas of the following
compounds: (a) 3-hexyne; (b) 1,3-pentadiene;
(c) 3,3-dimethylcyclobutene; (d) 3,4-diethyl-1-
hexyne.
*029.Write the IUPAC names for the following compounds.*030.Repeat Exercise 29 for(c) CH 3 CmCCH 3*031.Each of the hydrocarbon families has members that
are cyclic hydrocarbons. (a) What is a cyclic hydrocar-
bon? (b) Write the structural formula of one example
of each of the following: (i) cycloalkene; (ii) cycloalkane;
and (iii) cycloalkyne.Aromatic Hydrocarbons
*032.(a) What distinguishes an aromatic compound from other
cyclic compounds? (b) What is the principal source of
aromatic hydrocarbons?
*033.(a) The structure for benzene is sometimes drawn as a
hexagon enclosing a circle; what is the meaning of the
circle? (b) Write the structural formulas of the three most
common aromatic hydrocarbons.
*034.(a) What is a phenyl group? (b) How many isomeric
monophenylnaphthalenes are possible?
*035.There are only three isomeric trimethylbenzenes. Write
their structural formulas, and name them.
*036.(a) How many isomeric dibromobenzenes are possible?
(b) What names are used to designate these isomers?
*037.Write the structural formulas for the following
compounds: (a) p-difluorobenzene; (b) ethylbenzene;
(c) 1,3,5-tribromobenzene; (d) 1,3-diphenylbutane;
(e) p-chlorotoluene.(f )CH 3 CH 2 CHCH 2 CH 3CH 2 CH 2 CH 3(e)CH 3 CH 2 CHCH 3CH 2 CH 3(b)CH 3 CHCH 2 CH 3CH 3CH 3(d)CH 3 C CHCH 3CH 3
(a)(b)CH 2 C(CH 3 ) 2 (d)CH 3(c)CH 3 CHCHCH 2 CH 3CH 3CH 3CH 3 CCH 2 CH 2 CH 3CH 3(a)