Organic Worksheets

Organic Chemistry 2010 Baverstock/Kailley Page 5
Alkanes, Alkenes, Alkynes and Cycloalkanes

You can print a copy of every organic sheet.
For each drawing question you must write down the name, draw the structural diagram and
number the carbons and circle the branches.
For each naming question you must copy the drawing, number the drawing and write the
name.

A. Draw the structural diagrams:
1. pentane
2. methane
3. heptane
4. hept-3-yne
5. ethyne
6. but-1-yne
7. hexa-1,2-diene
8. penta-1,4-diyne
9. octa-1,4,7-triyne
10. propene
11. 4-propylheptane
12. 6-methylhept-3-yne
13. 3-ethyl-2-methyl-5-propyloctane
14. 4-ethyl-5-methylhex-2-yne
15. 3,4,5,-triethylheptane
16. 2,2,5,5-tetramethylhex-3-yne
17. 1,1-diiodopentane
18. 3-ethyl-1-fluoro-4,5-dimethylhexane
19. 1,4-dimethylcyclobut-1-ene
20. 2-cyclopropylpentane
21. methylpropane
22. 1,1-diiodo-2-methylcyclopropane
23. 1-butylcyclopent-1-ene
24. 6,6-dichloro-4-cyclobutyl-4-methylhex-2-yne
25. dimethylbut-2-ene

B. Name the following:

1.
C H
3
CH
3

2.
C H
3
CH
3

3
CH
3
H
H
H

4.
C H
CH
3

5.
C H
3
CH
3

6.
H
H
H
H
H
H

7.
C H
3
CH
3

8.
C H
3
CH


9.
C H
3
CH
3
CH
3
H
C H
3

10.
C H
3
CH
3
H
H
H

11.
CH
3
C H
3
CH
3
H
H
H

12.
C H
3
CH
CH
3
CH
3

13
C H
3
CH
3
C H
3
Br

14.
C H
3
C H
3
Cl
Cl

15.
C H
3
CH
3
CH
3
C H
3

16.
C H
3
CH
3
C H
3
CH
3

17.
C H
3
CH
3
CH
3
CH
3
CH
3

18.
F
F

19.
CH
3
CH
3
Br
Br

20.

21.
Br
Br

22.
CH
3
C H
3
C H
3
CH
3

23.
CH
3
C H
3

24
C H
3
CH
3
.

C. Write the name or formula for the following hydrocarbons. Position numbers are not
necessary.

1. C
7
H
16

2. C
2
H
6

3. C
5
H
8

4. C
4
H
8


5. C
10
H
16

6. C
9
H
16

7. C
6
H
14

8. C
3
H
4

9. propene
10. 2-methylhexane
11. 3-ethylhept-1-ene
12. dec-1-yne
13. 2,2-dimethyloctane
14. 2,3,4-triethylcyclohexene
15. propylcyclopropane
16. 1-chloropentane
17. octa-1,3-diene
18. hepta-1,4-diyne

Isomer Practice

A. Structural isomer questions

1. Draw and name two structural isomers of hexane that have a single methyl group.
2. Draw and name four structural isomers that have two methyl groups attached to pentane.
3. Draw and name all the isomers of octane.
4. Draw and name all the isomers of chloropentane.
5. Draw and name all the isomers of dichloropentane that have two methyl groups.
6. Draw and name three structural isomers of 3-methylpent-1-yne. No rings can be used.

B. Geometrical isomer questions

1. Draw the following structures.
a. cis-hex-2-ene
b. hex-2-yne
c. cis-4-methyloct-2-ene
d. trans-2,2-dimethyldec-4-ene
e. but-1-yne
f. trans-4-methylhept-2-ene

2. Which of the following can exhibit geometrical isomerism?
a. pent-1-ene
b. 2-methylhex-3-ene
c. 2-methylpent-2-ene
d. non-4-yne
e. 1-chloroprop-1-ene
f. 3-ethyldec-3-ene
g. cyclobutane
h. 2,3-dibromopent-2-ene


3. Name the following:

a.
C H
3
CH
3
H H

h.
C H
3
CH
3
H
H

b.
CH
3
Cl
Cl Cl

i.
C H
3
CH
3
H
H

c.
CH
3
H
H
F

j.
CH
3
C H
3
CH
3
CH
3
C H
3

d.
C H
3
CH
3
H
H

k.
C H
3
Cl
Cl
CH
3
C H
3

e.
C H
3
CH
3
CH
3
H

l.
C H
3
CH
3
H H

f.
F
F
CH
3
CH
3

m.
Br
Br
Cl
F

g.
Br
Br H
Br

n.
C H
3
C H
3
CH
3
CH
3

4. Draw the following. (use bow-tie structures around the double bond as above)

a. cis-pent-2-ene
b. trans-non-3-ene
c. cis-1,3-difluorobut-1-ene
d. trans-4,5-dichloronon-4-ene
e. propene
f. cis-4,4-dimethylpent-2-ene
g. trans-2,3-dibromobut-2-ene

h. cis-1-fluoro-4,5-dimethylhex-2-ene
i. 1,1-diiodobut-1-ene
j. 2,3-dichlorobuta-1,3-diene

C. Aromatic hydrocarbons questions

1. Draw all of the resonance structures of 1,4-dichlorobenzene.
2. Draw all of the structural isomers of 1,4-dichlorobenzene.
3. What is the difference between resonance structures and structural isomers?
4. Below is a picture of naphthalene. Draw all of the resonance structures of naphthalene.

5. Below is a picture of anthracene. Draw all the resonance structures of anthracene.

6. Below is a picture of phenanthrene. Draw all the resonance structures of phenanthrene.

a.
C H
3

b.
CH
3
CH
3
Cl

c.
CH
3
CH
3
CH
3
CH
3
C H
3
C H
3

d.
Br
Br Br
Br

e.
CH
3
CH
3
C H
3

f.
Br Br

8. Draw the following:
a. cyclobutylbenzene
b. 1,2-dipropylbenzene
c. 1,4-dichloro-2-ethylbenzene
d. bromobenzene
e. 1-fluoro-2-propylbenzene
f. 1,2,4-trimethylbenzene


Alchohols, Aldehydes and Ketones Practice

A. Draw the following:

1. pentan-1-ol
2. heptane-1,2-diol
3. 3,3-dimethylbutan-2-ol
4. 4-ethyl-2-methylhexane-1,2-diol
5. 4-methylpent-3-en-1-ol
6. 8-methylcyclooct-4-en-1-ol
7. trans-5-fluoropent-2-en-1-ol
8. 1-cyclobutylpropan-2-ol
9. 2-ethyl-4-propylcyclohexa-2,4-dien-1-ol
10. 3-chloroprop-1-yn-1-ol
11. butanal
12. 2-methylpentanal
13. 3-cyclopropylbutanal
14. trans-oct-6-enal
15. 3-cyclohexylpropanal
16. cis-hex-3-enedial
17. 4-hydroxybutanal
18. cis-3-propylhept-4-enal
19. methylpropenal
20. 5-ethyl-3,4,6-trimethyloctanal
21. propanone
22. 6-methylheptan-3-one
23. 2-butylcyclopropanone
24. dimethylbutanone
25. 5-methylhex-4-en-2-one
26. 5-chlorocyclohex-2-en-1-one
27. cis-3,4-dimethylhex-3-en-2-one
28. 6-ethyl-6-methylocta-1,4-diyn-3-one
29. 3,4,5-trichloroheptane-2,6-dione
30. 2,3-dicyclobutyl-2,3-diethylcyclopropanone

1.
C H
3
CH
3
OH

2.
C H
3
CH
3
O H CH
3

3
CH
3 C H
3
CH
3
OH

4.
C H
3
CH
3
O H
OH

5.
C H
3
O H
H
H

6.
OH
OH


7.
C H
3
C H
3
CH
3
C H
3
CH
3
OH

8.
C H
3
CH
3
OH
OH H
H

9.
C H
3
OH

10.
C H
3
CH
3
OH
H

11.
CH
3
O
H

12.
C H
3
O
CH
3
CH
3
CH
3
H

13
C H
3
CH
3
O
CH
3
H

14.
C H
3
O
H

15.
O
O
CH
3
C H
3
H H

16.
CH
3
CH
3
CH
3
O
H

17.
CH
3
O
CH
3
CH
3
C H
3
H

18.
C H
3
O C H
3
H

19.
CH
3
O
CH
3
H
H
H

20.
OH
O CH
3
H

21.
C H
3
CH
3
O

22.
C H
3
C H
3
CH
3
O


23.
O
C H
3
CH
3

24.
CH
3
CH
3
CH
3
CH
3 O

25.
C H
3
CH
3
O
O

26.
C H
3
OH
O

27.
C H
3
CH
3
O

28.
C H
3
CH
3
O
CH
3
H
H

29.
O
C H
3
CH
3
CH
3
H
H
H
H
H

30.
C H
3
CH
3
C H
3
OH
O

C. Isomers:

1. Draw and name all the isomers for C
5
H
11
CHO.
4
H
9
OH.
3. Draw and name all the isomers for a ketone with 5 carbons, 1 oxygen and 8 hydrogen.

D. Write the name or formula for the following aldehydes and alcohols.
1. C
2
H
5
OH
2. C
3
H
7
CHO
3. C
5
H
9
OH
4. C
8
H
15
CHO
5. C
4
H
7
CHO
6. 2-methylpropan-1-ol
7. octanal
8. 2,2-dimethylheptan-3-ol
9. but-1-en-2-ol
10. pent-3-enal
11. pent-4-yn-2-ol
12. 2-ethylhex-5-ynal

Carboxylic Acids, Esters, Amides

A. Draw the following compounds.

1. 5-ethylheptanoic acid
2. 2,2-difluoropropanoic acid
3. trans-but-2-enoic acid
4. cis-2,3-dibromo-4-fluorobut-2-enoic acid

5. 4,4-dimethylpent-2-ynoic acid
6. 4-ethyl-3-methylhex-3-enoic acid
7. cis-but-2-enoic acid
8. trans-5,5-dichlorohex-3-enoic acid
9. cis-4-cyclopropylbut-2-enoic acid
10. methanoic acid
11. ethyl propanoate
12. ethyl trans-but-2-enoate
13. ethyl 2,3-difluorobut-3-enoate
14. methyl prop-2-ynoate
15. methyl 2,2-difluorobut-3-ynoate
16. propyl butanoate
17. methyl cis-pent-2-enoate
18. cyclopropyl trans-but-2-enoate
19. cyclobutyl 3,3-dibromobutanoate
20. methyl trans-4-methylpent-2-enoate
21. ethanamide
22. cis-but-2-enamide
23. 2,2-dibromopropanamide
24. methanamide
25. cis-2,3-dimethylpent-2-enamide
26. but-3-ynamide
27. N-methylbutanamide
28. cis-4,4-dimethylpent-2-enamide
29. 4,4-dibromo-N,N-dimethylpentanamide
30. trans-5,5-difluoropent-2-enamide

B. Name the following compounds.
1.
CH
3
O
O H

2.
C H
3
O
OH
C H
3
H

3.
CH
3
O
O H
H H

4.
CH
3
O
O H
H
H

5.
O
OH
I
I
H

6.
C H
3
O
OH H
H

7.
C H
3
O
OH

8.
C H
3
O
OH


9.
C H
3
O
OH C H
3

10.
C H
3
O
OH
CH
3
H

11.
CH
3
O
O CH
3

12.
C H
3
O
O
CH
3
CH
3
H

13.
C H
3
O CH
3
O

14.
C H
3
O
C
O
H
H
H

15.
F
F
F
O
O CH
3

16.
O
O CH
3

17.
O
O CH
3
H
H

18.
C H
O
O
CH
3

19.
C H
3
O
O
CH
3
H H

20.
CH
3
O
O
CH
3
CH
3
H

21.
C H
3
N H
2
O

22.
NH
2
O
H
H
H

23.
NH
2
O
CH
3
H
H

24.
O
NH
2
Br
Br

25.
C H
3
O
NH
2
H
H

26.
O
NH
2
H
H
O
N H
2


27.
CH
3
O
N C H
3
H

28.
O
N
CH
3
CH
3
H
H
H

29.
C H
3
O
NH
2
H
H

30.
CH
3
O
N C H
3
H
H
H

C. Draw the following isomers.

6
H
13
COOH
4
H
9
CONH
2

Amines, Ethers, Nitro and Reaction Practice

A. Draw the following:

1. 4,5-dimethylhexan-2-amine
2. cyclopent-2-en-1-amine
3. 2,2-diethylheptan-1-amine
4. 7-aminoheptan-3-one
5. propyl 7-amino-2-ethylhept-5-ynoate
6. 6-amino-2-methyloctanal
7. N,N,3-triethyl-3-methylhexan-1-amine
8. 4-ethoxy-1-methoxypentane
9. 1-butoxybut-1-yne
10. cis-6,7-dimethoxyoct-6-enoic acid
11. 3-ethoxycycloheptene
12. 1,2-dimethyl-4-nitrobenzene
13. 3-cyclopropoxyoctane
14. 4-methoxy-N-methylbutanamide

1.
C H
3
CH
3
NH
2

2.
CH
3
C H
3
N
CH
3
H

3
CH
3
OH
N H
2

4.
C H
3
CH
3
NH
2
H
H


5.
C H
3
NH
2
O
O H

6.
C H
3
CH
3
NH
2
NH
2
NH
2
CH
3

7.
NO
2
CH
3
N
C H
3
C H
3

8.
C H
3 O
CH
3

9.
C H
3
O NH
2
O
CH
3

10.
CH
3
O
O
CH
3
O
C H
3

11.
C H
3
O
O
CH
3
H
H

12.
O
O
O
CH
3
CH
3

13.
O
O
O
C H
3
CH
3
C H
3

14.
NO
2
O
CH
3
H
H H
H
H H

C. Write the name or formula for the following carboxylic acids, amines and amides.

1. C
3
H
7
COOH
2. C
5
H
11
NH
2

3. C
2
H
5
CONH
2

4. C
3
H
5
COOH
5. C
5
H
7
NH
2

6. pent-2-enoic acid
7. 2,2-dimethylpropanoic acid
8. prop-2-en-1-amine
9. hexanamide
10. 2-propylheptanoic acid

D. For each reaction draw structural diagrams for all of the organic based compounds and write
formulas for the simple ionic and covalent compounds. Name the products.

1. 2-methylpentanoic acid + lithium hydroxide
2. 3,3-diethylhexanoic acid + potassium hydroxide
3. hexan-1-ol + benzoic acid
4. pentan-1-ol + cis-2-methyloct-6-enoic acid
5. pentanoic acid + butan-1-amine
6. decane (write the molecular formula) + oxygen
7. hexan-1-amine + water
8. nitric acid + 2-methylpropan-1-amine

E. Draw all of the organic structures. Write the formula for the inorganic substances. Name
the reactants and/or products.

1. 3,4-dimethylhexanoic acid + potassium hydroxide
2. sodium 2-ethylpentanoate + water
3. Trans-pent-3-enoic acid + water
4. hept-5-ynoate + hydronium ion
5. butan-1-ol + 2,3-dichlorohexanoic acid
6. propyl trans-2,3-dihydroxyprop-2-enoate + water
7. butan-2-ol + ethanoic acid

F. Combustion Reactions

1. What are the products of a hydrocarbon combustion reaction?

2. Write the balanced reactions for the combustion reactions. Write everything as formulas!
Balanced reactions must have the simplest whole number coefficients (no fractions). Do
not write one as a coefficient.

a. propane is burned (means combustion or reacts with oxygen)
b. hexane is burned
c. cyclobutane is burned
d. ethanol is burned
e. pentanal is burned

Organic Chemistry Review

1. Why does carbon make-up the backbone of all organic compounds?

2. Which organic compounds are saturated? Unsaturated?

3. Name properties of the following:

a. alkanes
b. alkenes
c. alcohols
d. carboxylic acids
e. amines
f. ethers
g. esters
h. benzenes

4. Write molecular formulas for the following:

a. 3-methyloctane
b. methylcyclopentane
c. 1,2-dichlorohexane
d. propan-1-ol
e. butanoic acid
f. 3-ethylhept-1-ene
g. cyclobutyne
h. 3-propylcyclononene

5. Draw and name an example of an organic:

a. acid
b. base
c. beverage alcohol

6. Which of the following are miscible in water?
a. alkanes
b. alcohols
c. benzenes
d. carboxylic acids
e. amines

7. Which is more reactive?
a. alkanes or alkenes
b. alkanes or alcohols
c. ketones or carboxylic acid

8. For each reaction draw structural diagrams for all of the organic based compounds and write
formulas for the simple ionic and covalent compounds. Name the products.

a. hexanoic acid + potassium hydroxide
b. propanoic acid + water
c. heptan-3-amine + hydrochloric acid
d. ethanamine + water
e. butanoic acid + propan-1-amine
f. butan-1-ol + heptanoic acid
g. decan-1-ol + 2,3-dimethylpent-4-enoic acid
h. propane + oxygen

9. Draw and name one set of geometrical isomers for C
4
H
8
.

10. Draw and name all the structural isomers for C
5
H
8
.

11. Draw the following:

a. 2,2,4-trimethylpentane
b. trans-hex-3-ene
c. 4,4-dimethylpent-2-yne
d. 1,1-dibromo-3-chlorobut-1-ene
e. 2,4-dimethyl-1,3,5-trinitrobenzene
f. butane-1,2-diol
g. pent-3-yn-2-one

h. but-3-enoic acid
i. 2,3,4-trimethylpentanal
j. 2,2-dimethylheptan-3-one
k. ethyl cis-2-fluoropent-3-enoate
l. N-ethyl-N,4,4-trimethylocta-5,7-diynamide
m. 3-ethylpentane-1,2-diamine
n. butyl cis-2,2-dimethylhex-3-enoate


a.
C H
3
CH
3
CH
3

b.
C H
3
C H
3
CH
3
CH
3
C H
3
CH
3

c.
CH
3
CH
3
CH
3
H
H
H

d.
CH
3
CH
3
C H
3
H
H

e.
CH
CH
3
C H
3

f.
C H
CH
3
CH
3

g.
C H
3
Br
Br Cl
H

h.
C H
3
CH
3
OH

i.
NO
2
O
2
N

j.
O
O H
H
H
H

k.
C H
3
CH
3
OH
OH
CH
3

l.
CH
3
O H
CH
3
CH
3
CH
3

m.
CH
3
O
OH
H
H

n.
C H
3
O
H

o.
C H
3
CH
3
O
C H
3
CH
3


p.
C H
3
O CH
3
O

q.
C H
3
O
CH
3
O
CH
3
CH
3

r.
C H
3
O
NH
2

s.
C H
3
O
NH
2
CH
3
H

t.
C H
3
CH
3
N
CH
3
C H
3

u.
F
F
NH
2

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Organic Chemistry 2010 Baverstock/Kailley Page 5

Alkanes, Alkenes, Alkynes and Cycloalkanes

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