Organic Problems
1. Draw and name the isomers of C7H16 .
2. Name the following.
CH3
a.
CH3CHCH2CCH3
CH3
CH2
CH3
CH3
e.
CH3CH2CCH2CCH3
HC
CH3 CH3
c.
CCH2CCH3
CH3
CH3 CH3
b.
CH3 CH3
d.
CH3
CH3
f.
CH3
CH3CCH2CH2CHCHCH3
CH2CH3
CCCH2CH3
CH3
CH3
CH3
CH2
CH2
CH3CHCH2CH2CCH3
CH3
3. Name the following
a.
c.
b.
d.
4. Draw structural formulas for the following.
a. 2,3,5,6-tetramethyloctane
b. cis-3,4-dimethyl-3-hexene
c. 1-ethyl-3-methylcycloheptane
d. 4,4-dimethyl-2-pentyne
e. 6-methyl-2,4-nonadiene
f. ethylcyclopentane
g. 2,3-dimethyl-1,3-butadiene
5. Draw and name 12 isomers that have the formula C6H12.
e.
6. Complete and balance the following.
a. CH3CH=CH2 + HCl →
b. CH3CH=CHCH3 + Br2 →
c. CH3C≡CH + 2 HBr →
d. CH3C≡CCH3 + 2 F2 →
e. 1,3-cyclohexadiene + excess chlorine gas →
AlCl3
f. 1,4-dimethylbenzene + chlorine gas →
7. Name the following.
a.
CH2CH2
OH
f.
CH3
CH3CHCH2CH
Br Br
CH3
b.
O
g.
CH3CHCH2CH3
CH3CCH2CHCH3
NH2
CH3
c.
CH3
h.
CH3
HC
CH3CHCH2CHCHCH3
CCH2CHCH2CH3
CH2CH3 CH3
CH3
d.
CH3CH
i.
CHCH2CCH3
CH3
e.
O
j.
CH3CH2CHCH
CH3
O
CH3CH2CHCH2COH
CH3
8. Draw structural formulas for the following:
a. 3-hexanone
b.
trans-3-hexene
c. iodobenzene
d. propylbutanoate
e.
2,3,4-trimethylhexane
f. 3-methyloctanal
g. 2-pentyne
h.
1,2,3-triethylcyclohexane
i. butylpropanoate
j.
the fat formed by hexanoic acid
k. the oxidation product of 2-pentanol
2
9. Write formulas ``for the products and name all organic compounds in the following reactions:
a. CH3C
CH2 +
HI
CH3
O
b.
CH3CH2CHC
H+
OH + CH3OH
CH3
c.
[O]
CH3CH2CHCH2CH3
OH
d.
+ Cl2
e.
CH3CH2CH2CH2OH
f.
CH3CH2C
CH
[O]
+
[O]
HCl
O
g. CH3CH2C
O
CH3 +
NaOH
10. For the following compound, write a complete, expanded structural formula (with all C-H
bonds, etc. clearly shown). Also, name the compound.
O
CN
Name:
11. In the structure above, the hybridization at the carbon atom of the CN group is
and the bond angles around that carbon are about
3
degrees.
12. Write chemical formulas for each of the following compounds. You may use partially condensed
formulas (e.g. CH3-CH2-OH for ethanol) as long as the correct number of hydrogens are shown
on each carbon and the C-C framework and any functional groups are clearly shown.
a.
b.
c.
d.
aniline
acetone
"MTBE" (methyl tert-butyl ether)
4-amino-3-methylpentanal
13. Consider all possible carbonyl compounds having the formula C4H6O.
a. Write expanded structural formulas for as many carbonyl isomers of C4H6O as you can
(there are more than five). (Note: Points will be deducted if the same structure is drawn more
than once but bonus points are available for each correct one beyond five!)
b. One of the above carbonyl isomers (call it compound A) can be cleanly converted in a twostep sequence of reactions to 1,3-butadiene (compound C). Which carbonyl isomer is
compound A? Write complete structural formulas for compounds A, B, and C in the reaction
sequence below.
A
H2
H+
B
C
∆
14. Write complete, systematic names for:
CH3
CH3 CH CH CH CH3
CH2 CH2
C N
O
H C CH2
CH2
CH
CH2
CH3
CH3
C O CH
O
H2C CH3
CH3
OH
H3C CH2 CH CH CH2 CH CH3
H2C CH2 CH3
4
15. Write complete, specific structural formulas for all of the organic reactants and products in each
reaction.
an ester
2-hexyne
NaOH
H2
sodium acetate
cis-2-hexene
H2O
+
3-pentanol
an alcohol
16. For the following compound, write a complete expanded structural formula (with all C-H bonds, etc.
clearly shown). Also, name the compound.
O
5
Organic Problems (Answers)
Note that all structures are drawn with only skeletal carbons for simplicity in the drawing
program. With pencil and paper you will BE REQUIRED to show the correct number of
hydrogen atoms attached to each carbon. Please see me if you have questions about this.
1. Draw and name the isomers of C7H16 .
Heptane
C C C
C
C
C
C
2-methylhexane
C
3-methylhexane
C
2,2-dimethylpentane
C
C C C C C
2,3-dimethylpentane
C
C
C
C
C
C
C
C
C
C
C
3,3-dimethylpentane
C
C
3-ethylpentane
C C
C
C
C
C
C
C
C
C
C
C
C C C C C
2,4-dimethylpentane
C
C
C
C
C
C
CH3
CH2
C
CH3
e.
HC
CH3 CH3
CCCH2CH3
CH3
2,2,4,4-tetramethylhexane
3,3-dimethyl-1-pentyne
CH3
f.
CH3CCH2CHCHCHCH3
CH2CH3
C
C
2,4,4-trimethyl-1-pentene
CH3 CH3
CH3
C
CH3
CH3CH2CCH2CCH3
c.
C
CCH2CCH3
CH3
2,2,4-trimethylpentane
b.
C
CH3 CH3
d.
CH3CHCH2CCH3
C
CH3
CH3
CH3
CH2
CH2
CH3CHCH2CHCHCH3
2,3,6,6-tetramethyloctane
CH3
3,3,6-trimethyloctane
6
C
2,2,3-trimethylbutane
C
C
2. Name the following.
CH3
a.
C
C
3. Name the following
a. 4-methyl-2-pentene
b. 2,3,4-trimethylhexane
c. 3,6,dimethyl-1,4-cyclohexadiene
d. 2,4-heptadiene
e. 1,2-dimethylcyclopentane
4. Draw structural formulas for the following. (only carbons are usually shown for simplicity in my
drawing program.)
a. 2,3,5,6-tetramethyloctane
C
C
C
C
C
C
C
C
C
C
C
C
b. cis-3,4-dimethyl-3-hexene
C
C
C
C
C
C
C
C
c. 1-ethyl-3-methylcycloheptane
CH3CH2
CH3
d. 4,4-dimethyl-2-pentyne
C
C
C
C
C
C
C
e. 6-methyl-2,4-nonadiene
C
C
C
C
C
C
C
C
C
C
f. ethylcyclopentane
CH2CH3
g. 2,3-dimethyl-1,3-butadiene
C
C
C
C
C
C
7
5. Draw and name 12 isomers that have the formula C6H12.
C
C
C
C
C
C
C
C
1-hexene
cyclohexane
C
C C C
3-hexene
C
C
C
C
C C C C C
2-methyl-1-pentene
C
C
C
C
C
C
C
C
C
C
C
C
3-methyl-1-pentene
C
C
C
C C C C
4-methyl-1-pentene
C
2-hexene
C
C
C
C
C
C C C C
2-methyl-2-pentene
C
C
C
C
2,3-dimethyl-1-butene
C
C
C
C
3,3-dimethyl-1-butene
C
C
C
C
C
C
Cl
→ CH3CHCH3
Br Br
b. CH3CH=CHCH3 + Br2 → CH3CHCHCH3
c. CH3C≡CH + HBr →
H3C-CBr2-CH3
d. CH3C≡CCH3 + F2 → CH3CF2CF2CH3
Cl
Cl
e. 1,3-cyclohexadiene + excess chlorine gas →
Cl
Cl
CH3
Cl
AlCl3
f. 1,4-dimethylbenzene + chlorine gas →
+ HCl
CH3
8
C
2,3-dimethyl-2-butene
6. Complete and balance the following.
a. CH3CH=CH2 + HCl
C
C
C
4-methyl-2-pentene
3-methyl-2-pentene
C
C
C
C
7. Name the following.
CH2CH2
a.
OH
f.
CH3
CH3CHCH2CH
Br Br
1,2-dibromoethane
CH3
4-methyl-2-pentanol
O
b.
CH3CHCH2CH3
g.
CH3CCH2CHCH3
NH2
2-aminobutane
CH3
4-methyl-2-pentanone
c.
CH3
h.
CH3
HC
CH3CHCH2CHCHCH3
CCH2CHCH2CH3
4-methyl-1-hexyne
CH2CH3 CH3
2,3,5-trimethylheptane
CH3
d.
CH3CH
i.
CHCH2CCH3
1,3-cyclopentadiene
CH3
5,5-dimethyl-2-hexene
O
e.
CH3
j.
CH3CH2CHCH
O
CH3CH2CHCH2COH
3-methylpentanoic acid
CH3
2-methylbutanal
8. Draw structural formulas for the following:
b trans-3-hexene
a. 3-hexanone
O
. CH3
CH3
CH2 C CH2 CH2 CH3
d. propylbutanoate
O
CH3 CH2 CH2 C
C
H
e
.
O CH2 CH2 CH3
g. 2-pentyne
CH3
CH2
C CH2 CH3
H
CH2
CH CH CH CH2 CH3
1,2,3-triethylcyclohexane
CH2CH3
CH3CH2
9
I
CH3
CH3 CH3 CH3
CH3CH2
iodobenzene
C
2,3,4-trimethylhexane
CH3
h
.
C
c
.
f. 3-methyloctanal
CH3
O
CH3 CH2 CH2 CH2 CH2 CH CH2 C H
i.
butylpropanoate
j. the fat formed by hexanoic acid
O
CH3 CH2 C
O
O CH2 CH2 CH2 CH3
CH2
O
C
CH2CH2CH2CH2CH3
CH
O
C
CH2CH2CH2CH2CH3
CH2
O
O
C
CH2CH2CH2CH2CH3
O
k. the oxidation product of
2-pentanol
O
CH3
C CH2 CH2 CH3
9. Write formulas for the products and name all organic compounds in the following
I
a. CH3C
CH2 +
HI
CH3C
CH3
methylpropene
CH3
2-iodo-2-methylpropane
O
b.
CH3CH2CHC
O
H+
OH + CH3OH
CH3CH2CHCH2CH3
CH3CH2CHC
OCH3
CH3
methyl-2-methylbutanoate
CH3
2-methylbutanoic acid
c.
CH3
[O]
`
CH3CH2CCH2CH3
O
3-pentanone
OH
3-pentanol
Cl
d.
+ Cl2
Cl
1,2-dichlorocyclohexane
cyclohexene
O
e.
CH3CH2CH2CH2OH
1-butanol
[O]
O
[O]
CH3CH2CH2CH
butanal
10
CH3CH2CH2COH
butanoic acid
reactions:
f. CH3CH2C
CH
+
HCl
CH3CH2CCl2 CH3
2,2-dichlorobutane
1-butyne
O
O
g. CH3CH2C
O CH3 +
methyl propanoate
NaOH
CH3CH2C O Na
sodium propanoate
+ CH3OH
methanol
10. For the following compound, write a complete, expanded structural formula (with all C-H
bonds, etc. clearly shown). Also, name the compound.
H3C
CH2
O
CH
CH3
C
C
H
CH
C
C
CH
C N
C
C
CH3
H
C
H
H
H
Name:
2-cyano-4-methyl-5-phenyl-3-heptanone
11. In the structure above, the hybridization at the carbon atom of the CN group is sp and the bond
angles around that carbon are about 180 degrees.
12. Write chemical formulas for each of the following compounds. You may use partially condensed
formulas (e.g. CH3-CH2-OH for ethanol) as long as the correct number of hydrogens are shown
on each carbon and the C-C framework and any functional groups are clearly shown.
a. aniline
NH2
b. acetone
O
H3C
C
CH3
(c. "MTBE" (methyl tert-butyl ether)
CH3
H3C O C CH3
CH3
11
d. 4-amino-3-methylpentanal
CH3
H3C CH CH CH2
NH2
O
C H
13. Consider all possible carbonyl compounds having the formula C4H6O.
a. .Write expanded structural formulas for as many carbonyl isomers of C4H6O as you can
(there are more than five). (Note: Points will be deducted if the same structure is drawn more
than once but bonus points are available for each correct one beyond five!)
O
H
H C CH2
CH CH2
O C
H C
C
H C
C H
H
O C
C
O CH3
H C C CH2
CH3
C
H
H
H
H
O C C
O
H C
H
cis
O
H
H
CH3
H
trans
C
O
H
C C
H
H
CH CH2
H
H
C C
O
H3C C
CH3
C
C
CH2
CH3
CH3
H
O C C
C H
CH3
H
b..One of the above carbonyl isomers (call it compound A) can be cleanly converted in a twostep sequence of reactions to 1,3-butadiene (compound C). Which carbonyl isomer is
compound A? Write complete structural formulas for compounds A, B, and C in the reaction
sequence below.
H2
A
B
O
H C CH2
CH CH2
H+
C
∆
OH
H2
A
H2C CH2
H+
H2C
CH
12
B
∆
CH CH2
C
CH CH2
14. Write complete, systematic names for:
2-cyano-4-methyl-3-heptene
4-phenylhexanal
2-butyl benzoate
5-ethyl-4-methyl-2-octanol
15. Write complete, specific structural formulas for all of the organic reactants and products in each
reaction.
an ester
O
CH3
C
O
NaOH
sodium acetate
O
CH2CH3
CH3
CH
C
+
O- Na+
+
3-pentanol
OH
CH3
CH2
CH
CH2
CH3
CH2CH3
2-hexyne
CH3
C
C
CH2CH2CH3
H2
cis-2-hexene
an alcohol
OH H
H
H
H2
H2O
C
H2O CH3
C
CH2CH2CH3H
CH3
C
CCH2CH2CH3
H
H
16. For the following compound, write a complete expanded structural formula (with all C-H bonds, etc.
clearly shown). Also, name the compound.
O
4-ethyl-2-methyl-5-phenyl-3-heptanone
13