Organic Problems

1. Draw and name the isomers of C7H16 .

2. Name the following.

a. CH3 d. CH3 CH3

CH3CHCH2CCH3 CH2 CCH2CCH3

CH3 CH3 CH3

b. CH3 CH3 e. CH3

CH3CH2CCH2CCH3 HC CCCH2CH3
CH3 CH3 CH3

c. CH3 CH3 f. CH3 CH3

CH3CCH2CH2CHCHCH3 CH2 CH2
CH2CH3 CH3 CH3CHCH2CH2CCH3
CH3

3. Name the following

a. b.

c. d. e.

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.

6. Complete and balance the following.
a. CH3CH=CH2 + HCl
b. CH3CH=CHCH3 + Br2
c. CH3CCH + 2 HBr
d. CH3CCCH3 + 2 F2
e. 1,3-cyclohexadiene + excess chlorine gas

AlCl3
f. 1,4-dimethylbenzene + chlorine gas

7. Name the following.

a. CH2CH2 f. OH CH3

Br Br CH3CHCH2CH
CH3

b. O g. CH3CHCH2CH3
CH3CCH2CHCH3 NH2
CH3

c. CH3 h. CH3

CH3CHCH2CHCHCH3 HC CCH2CHCH2CH3

CH2CH3 CH3

d. CH3 i.
CH3CH CHCH2CCH3

CH3

e. O j. CH3 O

CH3CH2CHCH 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

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9. Write formulas ``for the products and name all organic compounds in the following reactions:

a. CH3C CH2 + HI
CH3

O
H+
b. CH3CH2CHC OH + CH3OH
CH3

[O]
c. CH3CH2CHCH2CH3
OH

d. + Cl2

[O] [O]
e. CH3CH2CH2CH2OH

f. CH3CH2C CH + 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.

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 degrees.

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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
b. acetone
c. "MTBE" (methyl tert-butyl ether)
d. 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 two-
step 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 H+
A B C

14. Write complete, systematic names for:

CH3 CH CH CH CH3
CH3 CH2 CH2 C N

O
H C CH2 CH2 CH CH2 CH3

O CH3
C O CH
H2C CH3

CH3 OH
H3C CH2 CH CH CH2 CH CH3
H2C CH2 CH3

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15. Write complete, specific structural formulas for all of the organic reactants and products in each
reaction.

NaOH
an ester sodium acetate + 3-pentanol

H2 H2O
2-hexyne cis-2-hexene 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.

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 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 2-methylhexane 3-methylhexane

C C C C C C C C C

C C C C C C C C C C C C
2,2-dimethylpentane 2,3-dimethylpentane 2,4-dimethylpentane
C C C C

C C C C C C C C C C C C C C C
C C
3,3-dimethylpentane 3-ethylpentane 2,2,3-trimethylbutane
C C C C

C C C C C C C C C C C C C C

C C C

2. Name the following.

a. CH3 d. CH3 CH3

CH3CHCH2CCH3 CH2 CCH2CCH3

CH3 CH3 CH3
2,2,4-trimethylpentane 2,4,4-trimethyl-1-pentene

b. CH3 CH3 e. CH3

CH3CH2CCH2CCH3 HC CCCH2CH3
CH3 CH3 CH3
2,2,4,4-tetramethylhexane 3,3-dimethyl-1-pentyne

c. CH3 CH3 f. CH3 CH3

CH3CCH2CHCHCHCH3 CH2 CH2
CH2CH3 CH3 CH3CHCH2CHCHCH3
2,3,6,6-tetramethyloctane CH3
3,3,6-trimethyloctane

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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

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

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5. Draw and name 12 isomers that have the formula C6H12.
C C C C C C C C C C C C
1-hexene 2-hexene

cyclohexane
C C

C C C C C C C C C C C C C C C C
3-hexene 2-methyl-1-pentene 3-methyl-1-pentene

C C C C

C C C C C C C C C C C C C C C C C C C C
4-methyl-1-pentene 2-methyl-2-pentene 3-methyl-2-pentene 4-methyl-2-pentene

C C C C C

C C C C C C C C C C C C
2,3-dimethyl-1-butene 2,3-dimethyl-2-butene
C
3,3-dimethyl-1-butene

6. Complete and balance the following.

Cl

a. CH3CH=CH2 + HCl CH3CHCH3

Br Br

b. CH3CH=CHCH3 + Br2 CH3CHCHCH3

H3C-CBr2-CH3
c. CH3CCH + 2 HBr

d. CH3CCCH3 + 2 F2 CH3CF2CF2CH3
Cl
Cl
e. 1,3-cyclohexadiene + excess chlorine gas

Cl
Cl

CH3
Cl
AlCl3
f. 1,4-dimethylbenzene + chlorine gas + HCl

CH3

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7. Name the following.
CH2CH2 f. OH CH3
a. Br Br CH3CHCH2CH
1,2-dibromoethane
CH3
4-methyl-2-pentanol

b. O g. CH3CHCH2CH3
CH3CCH2CHCH3 NH2
CH3 2-aminobutane
4-methyl-2-pentanone
c. CH3 h. CH3

CH3CHCH2CHCHCH3 HC CCH2CHCH2CH3

CH2CH3 CH3
4-methyl-1-hexyne
2,3,5-trimethylheptane

d. CH3 i.
CH3CH CHCH2CCH3
1,3-cyclopentadiene
CH3
5,5-dimethyl-2-hexene

e. O j. CH3 O

CH3CH2CHCH CH3CH2CHCH2COH
CH3 3-methylpentanoic acid
2-methylbutanal

8. Draw structural formulas for the following:

a. 3-hexanone b trans-3-hexene c iodobenzene
O . CH3 . I
CH2 H
CH3 CH2 C CH2 CH2 CH3 C C
H CH2
CH3
d. propylbutanoate e 2,3,4-trimethylhexane f. 3-methyloctanal
O . CH3 CH3 CH3 CH3 O
CH3 CH2 CH2 C O CH2 CH2 CH3 CH3 CH CH CH CH2 CH3 CH3 CH2 CH2 CH2 CH2 CH CH2 C H

g. 2-pentyne h 1,2,3-triethylcyclohexane
CH3 C C CH2 CH3 . CH2CH3
CH3CH2

CH3CH2

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i. butylpropanoate j. the fat formed by hexanoic acid
O O
CH3 CH2 C O CH2 CH2 CH2 CH3 CH2 O C CH2CH2CH2CH2CH3
CH O C CH2CH2CH2CH2CH3
O
CH2 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 reactions:

I
a. CH3C CH2 + HI CH3C CH3
CH3 CH3
methylpropene 2-iodo-2-methylpropane

O O
H+
b. CH3CH2CHC OH + CH3OH CH3CH2CHC OCH3

CH3 CH3
2-methylbutanoic acid methyl-2-methylbutanoate `

[O]
c. CH3CH2CHCH2CH3 CH3CH2CCH2CH3

OH O
3-pentanone
3-pentanol

Cl
d. + Cl2

Cl
cyclohexene 1,2-dichlorocyclohexane

O O
[O] [O]
e. CH3CH2CH2CH2OH CH3CH2CH2CH CH3CH2CH2COH
1-butanol butanal butanoic acid

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 Cl H
+ HCl
f. CH3CH2C CH + HCl CH3CH2C CH CH3CH2C CH
1-butyne
Cl H Cl H
2-chloro-1-butene 2,2-dichlorobutane

O O
g. CH3CH2C O CH3 + NaOH CH3CH2C O Na + CH3OH
methyl propanoate
sodium propanoate 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
H
CH C CH3
H C
C C CH CH
C C CH3 C N
H C 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)

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 CH3
H3C O C CH3
CH3
d. 4-amino-3-methylpentanal
CH3 O
H3C CH CH CH2 C H
NH2

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 CH3 H H
H C CH2 CH CH2 C C C C
O C H O C CH3
O
H H cis
H3C C CH CH2 trans
O
H C O CH3
O H CH3
H C C H C C CH2
C C
H C C H H H
H
H H O C C
O
CH2 CH3
H C
C H CH3
O C C
H C C H
CH3
H H

b..One of the above carbonyl isomers (call it compound A) can be cleanly converted in a two-
step 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 H+
A B C

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 O OH
H2
H C CH2 CH CH2 H2C CH2 CH CH2

A B
H+

H2C CH CH CH2
C
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.

NaOH
an ester sodium acetate + 3-pentanol

O O OH
CH2CH3 +
CH3 C CH3 C CH3 CH2 CH CH2 CH3
O CH O- Na+
CH2CH3

H2 H2O
2-hexyne cis-2-hexene an alcohol

OH H
H H
H2
C C H2O CH3 C CCH2CH2CH3
CH3 C C CH2CH2CH3
CH3 CH2CH2CH3H 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.

4-ethyl-2-methyl-5-phenyl-3-heptanone

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