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CHEM 219
Principles of Organic Chemistry
Modules 1-8 Problem Set
Portage Learning
MBOFFIN
Inside You Will Get:
» structural drawing and identification exercises
» nomenclature practice questions
» mechanism writing and prediction of reaction products
» stereochemistry assignments involving chiral centers and
configuration descriptors
» application -based problems requiring interpretation of reaction
conditions and outcomes.
,2. Classify the bonding between the given pairs of atoms as ionic, covalent, or polar
covalent. Use the table of electronegativities shown below to help with the classification.
H=21
Li=10 Be=1.5 B=20 C=25 N=30 0=3.5 F=40
Na=10 Mg=12 Al=15 Si=18 P=21 $=25 Cl=3.0
K=08 Ca=1.0 Ga=16 Ge=18 As =20 Se=24 Br=28
a. Br and Br = covalent
b. K and Cl = Ionic
c. P and Cl= Polar Covalent
d. C and O =Polar Covalent
e. Na and Br = Polar Covalent
,3. Define the term constitutional isomer.
CHANGE WORDING Answer:
Two (or more) different chemical compounds with the same molecular formula but different
connectivity between the atoms in their structural formulae.
4. Explain (using specific evidence) what makes the following two compounds
constitutional isomers of one another:
‘0" H H 0
L]
H—C—C—C—H
[l
H—C—C—C—H
Lo Vo
(a) (b)
Both compounds have a MF of C3H60 — same MF.
Compound “a” has a 3-carbon chain with a C=0 in the middle. No H atom connected to C
of C=0.
Compound “b” has a 3-carbon chain with a C=0 at the end. There is an H attached to the
C of the C=0.
5. What is the relationship between the compounds shown? Are they the same compound,
constitutional isomers, or two different compounds that are not related to one another? Explain.
HooH H ‘o
D S SN AL,
Vo oo
@) ()
Different compounds that are not related. They have different MF — (a) C3H8O, (b)
C3H60.
6. Identify each of the following carbon skeletons as linear (continuous), branched, or
cyclic.
, (a) (b) (©
a) Branched
b) Linear (continuous)
¢) Cyclic
7. On a piece of scratch paper, write out structural formulae for all of the constitutional isomers
possible for the MF C3H6F2. How many isomers are possible for this formula?
Answer:
FOUR (shown below)
F H H F F H F H F H
Hflfclfcfn ufcflfcfn ufc‘flfc‘fn H—(‘:—(‘:—(‘:—H
P ! Vi o
8. Characterize each of the following structural formula representations as either a dash,
condensed, super-condensed, or bond-line formula:
(CH,),COH CH,CH,CH,CH,CH,CH, NN H—C—c—c—H
(a) (b) (c) (d)
Answer:
a) Super-Condensed
b) Condensed
¢) Bond-line
d) Dash
Adobe
CHEM 219
Principles of Organic Chemistry
Modules 1-8 Problem Set
Portage Learning
MBOFFIN
Inside You Will Get:
» structural drawing and identification exercises
» nomenclature practice questions
» mechanism writing and prediction of reaction products
» stereochemistry assignments involving chiral centers and
configuration descriptors
» application -based problems requiring interpretation of reaction
conditions and outcomes.
,2. Classify the bonding between the given pairs of atoms as ionic, covalent, or polar
covalent. Use the table of electronegativities shown below to help with the classification.
H=21
Li=10 Be=1.5 B=20 C=25 N=30 0=3.5 F=40
Na=10 Mg=12 Al=15 Si=18 P=21 $=25 Cl=3.0
K=08 Ca=1.0 Ga=16 Ge=18 As =20 Se=24 Br=28
a. Br and Br = covalent
b. K and Cl = Ionic
c. P and Cl= Polar Covalent
d. C and O =Polar Covalent
e. Na and Br = Polar Covalent
,3. Define the term constitutional isomer.
CHANGE WORDING Answer:
Two (or more) different chemical compounds with the same molecular formula but different
connectivity between the atoms in their structural formulae.
4. Explain (using specific evidence) what makes the following two compounds
constitutional isomers of one another:
‘0" H H 0
L]
H—C—C—C—H
[l
H—C—C—C—H
Lo Vo
(a) (b)
Both compounds have a MF of C3H60 — same MF.
Compound “a” has a 3-carbon chain with a C=0 in the middle. No H atom connected to C
of C=0.
Compound “b” has a 3-carbon chain with a C=0 at the end. There is an H attached to the
C of the C=0.
5. What is the relationship between the compounds shown? Are they the same compound,
constitutional isomers, or two different compounds that are not related to one another? Explain.
HooH H ‘o
D S SN AL,
Vo oo
@) ()
Different compounds that are not related. They have different MF — (a) C3H8O, (b)
C3H60.
6. Identify each of the following carbon skeletons as linear (continuous), branched, or
cyclic.
, (a) (b) (©
a) Branched
b) Linear (continuous)
¢) Cyclic
7. On a piece of scratch paper, write out structural formulae for all of the constitutional isomers
possible for the MF C3H6F2. How many isomers are possible for this formula?
Answer:
FOUR (shown below)
F H H F F H F H F H
Hflfclfcfn ufcflfcfn ufc‘flfc‘fn H—(‘:—(‘:—(‘:—H
P ! Vi o
8. Characterize each of the following structural formula representations as either a dash,
condensed, super-condensed, or bond-line formula:
(CH,),COH CH,CH,CH,CH,CH,CH, NN H—C—c—c—H
(a) (b) (c) (d)
Answer:
a) Super-Condensed
b) Condensed
¢) Bond-line
d) Dash
