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Problem 1a
Using the general molecular formula for alkanes:
a. Predict the molecular formula of the C28 straight-chain alkane.
Problem 2a
Name the following alkanes and haloalkanes. When two or more substituents are present, list them in alphabetical order.
(a)
Problem 2b
Name the following alkanes and haloalkanes. When two or more substituents are present, list them in alphabetical order.
(b)
Problem 2c,d
Name the following alkanes and haloalkanes. When two or more substituents are present, list them in alphabetical order.
(c)
(d)
- All of the following names are incorrect or incomplete. In each case, draw the structure (or a possible structure) and name it correctly. a. 3-ethyl-4-methylpentane b. 2-ethyl-3-methylpentane c. 3-dimethylhexane
Problem 3
- The following names are all incorrect or incomplete, but they represent real structures. Draw each structure and name it correctly. a. 2-ethylpentane b. 3-isopropylhexane
Problem 3
- The heat of combustion of cis-1,2-dimethylcyclopropane is larger than that of the trans isomer. Which isomer is more stable? Use drawings to explain this difference in stability
Problem 3
Problem 3a
Write structures for the following compounds.
a. 3-ethyl-4-methylhexane
b. 3-ethyl-5-isobutyl-3-methylnonane
c. 4-tert-butyl-2-methylheptane
d. 5-isopropyl-3,3,4-trimethyloctane
Problem 4a,b,c
Provide IUPAC names for the following compounds.
a. (CH3)2CHCH2CH3
b. CH3—C(CH3)2—CH3
c.
Problem 4d,e,f
Provide IUPAC names for the following compounds.
(d)
(e)
(f)
Problem 5a,b,c
All of the following names are incorrect or incomplete. In each case, draw the structure (or a possible structure) and name it correctly.
a. 3-ethyl-4-methylpentane
b. 2-ethyl-3-methylpentane
c. 3-dimethylhexane
Problem 5d,e,f
All of the following names are incorrect or incomplete. In each case, draw the structure (or a possible structure) and name it correctly.
d. 4-isobutylheptane
e. 2-bromo-3-ethylbutane
f. 2,3-diethyl-5-isopropylheptane
Problem 6a
Give structures and names for
a. the five isomers of C6H14
Problem 7a
Draw the structures of the following groups, and give their more common names.
a. the (1-methylethyl) group
b. the (2-methylpropyl) group
c. the (1-methylpropyl) group
d. the (1,1-dimethylethyl) group
e. the (3-methylbutyl) group, sometimes called the 'isoamyl' group
Problem 8a
Draw the structures of the following compounds.
a. 4-(1,1-dimethylethyl)octane
Problem 8b
Draw the structures of the following compounds.
b. 5-(1,2,2-trimethylpropyl)nonane
Problem 8c
Draw the structures of the following compounds.
c. 3,3-diethyl-4-(2,2-dimethylpropyl)octane
Problem 9
Without looking at the structures, give molecular formulas for the compounds: (a) 4-(1,1-dimethylethyl)octane and (b) 5-(1,2,2-trimethylpropyl)nonane. Use the names of the groups to determine the number of carbon atoms; then use the (2n + 2) rule.
Problem 10a
List each set of compounds in order of increasing boiling point.
a. hexane, octane, and decane
Problem 10b
List each set of compounds in order of increasing boiling point.
b. Octane, (CH3)3C—C(CH3)3 and CH3CH2C(CH3)2CH2CH2CH3
Problem 11a
Draw Newman projections of the following molecules viewed from the direction of the blue arrows.
(a)
Problem 11b
Draw Newman projections of the following molecules viewed from the direction of the blue arrows.
(b)
Problem 11c
Draw Newman projections of the following molecules viewed from the direction of the blue arrows.
(c)
Problem 12
Draw a graph, similar to Figure 3-9, of the torsional strain of 2-methylpropane as it rotates about the bond between C1 and C2. Show the dihedral angle and draw a Newman projection for each staggered and eclipsed conformation.
Problem 13
Draw a graph, similar to Figure 3-11, of the torsional energy of 2-methylbutane as it rotates about the C2—C3 bond.
Problem 14
Draw a perspective representation of the most stable conformation of 3-methylhexane.
Problem 15a,b,c
Give IUPAC names for the following compounds.
Problem 16a,b
Draw the structure and give the molecular formula for each of the following compounds.
a. 1-ethyl-3-methylcycloheptane
b. isobutylcyclohexane
Problem 16c,d
Draw the structure and give the molecular formula for each of the following compounds.
c. cyclopropylcyclopentane
d. 3-ethyl-1,1-dimethylcyclohexane
Problem 16e,f
Draw the structure and give the molecular formula for each of the following compounds.
e. 3-ethyl-2,4-dimethylhexane
f. 1,1-diethyl-4-(3,3-dimethylbutyl)cyclohexane
