Structural Isomers1. Build the two isomers of butane, C4H10. Draw the complete, condensed and line

structural diagrams for each isomer.

2. Build the two isomers of C2H6O. Draw the complete and condensed structural diagrams for each isomer.

3. Build the two isomers of C2H7N. Draw the complete and condensed structural diagrams for each isomer.

4. Draw two isomers of C4H10O. The boiling points of the two compounds differ by approximately 70C. Which one would have the highest boiling point? Explain why the boiling points are so different.

Alkanes1. Draw and name the five possible noncyclic isomers of C6H14.

2. Name the following compounds:a) b)

c) d)

e) f)

Chem 20 Organic Chemistry Workbook Jill Agnew1

CH3 – CH2 – CH2 – CH3

CH3 – CH2 – C – CH2 – CH2 – CH3

CH3

CH3

CH3

CH3 – CH2 – CH2 – CH2 – CH – CH3

CH3 – CH – CH – CH – CH2 – CH2 – CH3

C2H5

C3H7CH3

CH3 – CH2 – CH – CH2 – CH3

CH2 – CH2 – CH3

CH2 – CH2 – CH2 – CH2 – CH3

CH2 – CH2 – CH3

Chemistry 30Organic Chemistry Workbook

Name:_____________________________________

g) h)

3. Why is the name 2-ethyl-2,4-dimethylhexane unsuitable for the following compound? What is the correct name of the compound?

4. Draw each of the following compounds:a) 3-ethylhexane b) 2,4-dimethylheptane

c) 3,4-diethyl-3-methylhexane d) 3-ethyl-4,5-dipropyloctane

e) 2,2-dimethylpentane f) octane

g) 2,2,3,3,4,4-hexamethyloctane h) 4-ethyl-4-propylheptane

Cycloalkanes1. Name each of the following compounds:a) b)

c) d)

Chem 20 Organic Chemistry Workbook Jill Agnew2

CH3 – CH – CH2 – CH2 – CH3

CH2 – CH2 – CH3

CH3 C CH2 CH

CH3

CH2

CH2

CH3

CH3

CH3

CH3 – CH2 – CH – CH2 – CH2 – CH3

CH2 – CH3

CH2 – CH3

CH3

CH3 CH3

CH2 – CH2 – CH2 – CH3

CH2 – CH3

CH3

e) f)

2. Draw each of the following compounds:a) propylcyclopentane b) 1-ethyl-4-methylcyclohexane

c) 1,1-diethylcyclobutane d) 1,2-diethyl-3-propylcyclobutane

e) 1,6-diethyl-3,4-dimethyl-1-propylcyclooctane f) cyclobutane

Alkenes1. Draw and name the five possible noncyclic isomers of C5H10.

2. Name the following compounds:a) b)

c) d)

e) f)

g) h)

3. Draw each of the following compounds:a) oct-3-ene b) 2,4-dimethylpent-2-ene

c) 4-ethyl-3-methylhex-2-ene d) methylpropene

e) 3-ethylpent-1-ene f) ethene

g) 5-ethyl-2,2,6-trimethylhept-3-ene h) 5-ethyl-3,4,6-trimethyloct-2-ene

Chem 20 Organic Chemistry Workbook Jill Agnew3

CH3CH3

CH2 – CH3

CH2 = CH2

CH2 = CH – CH2 – CH3

CH3 – CH – CH2 – CH2 – CH3

CH = CH – CH3

CH2 = CH – CH3

CH3 – CH2 – C = C – CH2 – CH3

CH2 – CH3

CH2 – CH3

CH2 – CH = CH – CH3

CH3 – CH2 – C = CH2

CH3

CH3 – CH = C – CH2 – CH3

CH – CH2 – CH3

CH3

CH2 – CH2 – CH3

CH2 – CH2 – CH3

CH3

Cycloalkenes1. Name the following compounds:a) b)

c) d)

2. Draw the following compounds:a) cyclooctene b) 1-ethyl-3-methylcyclopropene

c) 3,3-dimethyl-1-propylcyclopentene d) 4-butyl-1-methylcyclohexene

Alkynes1. Draw and name the three possible noncyclic isomers of C5H8.

2. Name the following compounds:a) b)

c) d)

e) f)

3. Draw the following compounds:a) non-3-yne b) 5-ethyl-4-propylhept-2-yne

c) 4,4-diethylhex-1-yne d) 2,2,3,3-tetramethyloct-4-yne

Chem 20 Organic Chemistry Workbook Jill Agnew4

CH2 – CH2 – CH3

CH3

C2H5

CH2 – CH3

CH3 CH2 – CH3

CH ≡ CH

CH ≡ C – CH2 – CH3

CH ≡ C – CH3

CH3 – CH – C ≡ C – CH2 – CH3

CH2 – CH3

CH3 – C ≡ C – CH3

CH ≡ C – C – CH3

CH2 – CH3

Aromatics1. Draw and name the three possible isomers of C6H4(CH3)2.

2. Name the following compounds:a) b)

c) d)

e) f)

g) h)

3. Draw the following compounds:a) 1-methyl-3-propylbenzene b) methylbenzene (toluene)

c) 2,2-dimethyl-3-phenylhexane d) phenylethene

e) ethylbenzene f) 4-phenyl-5-propyloctane

g) 1,4-diethylbenzene h) 4-methyl-2-phenylpent-2-ene

Chem 20 Organic Chemistry Workbook Jill Agnew5

CH3CH2 – CH3

CH2 – CH2 – CH3

CH3

CH3 – CH2 – CH – CH3

CH3

CH3

CH2 – CH2 – CH3

CH3 – CH2 – CH – CH2 – CH3

CH2

CH3

CH2 – CH – CH3

CH3

CH3

C2H5

CH3

C3H7

C2H5

CH3

4. Give two reasons why 1-methyl-3,4-diethylbenzene is an unsuitable name. Draw this compound and give the correct name.

Alcohols1. Name the following compounds:a) b)

c) d)

e) f)

g) h)

2. Draw each of the following compounds:a) butan-1-ol b) 2-methylbutan-2-ol

c) 4-ethyl-2-methylhexane-3,3-diol d) 2-phenylpentan-3-ol

e) 4-ethyl-2-methylphenol f) 2-methylcyclopropanol

Chem 20 Organic Chemistry Workbook Jill Agnew6

CH3 – CH2 – OH

CH3 – CH2 – CH2 – OH

CH3 – OH

OH

OHOH

CH3 – CH – CH2

OH

OH

CH3 – CH – CH – OH

CH3

OH

Organic Halides1. Name the following compounds:a) b)

c) d)

e) f)

g) h)

2. Draw each of the following compounds:a) 1,2-dibromo-3-chloropropane b) 1,4-diiodobenzene

c) 2-bromo-2-chloro-1,1,1-trifluoroethane d) triiodomethane

e) 4,4-difluoropentan-1-ol f) pentachlorophenol

Carboxylic Acids1. Name the following compounds:a) b)

c) d)

Chem 20 Organic Chemistry Workbook Jill Agnew7

F – CH2 – CH2 – CH2 – CH3

CH3 C CH2 C

Br

CH3

CH3 CH3

Br

C

F

F

FF

CH2Br – CF2 – CH2 – CH2Cl

I

OH

I

CH ≡ C – CH2Br CH3 – CH – CHF – CH2 – CH3

CH = CCl – CH3

Cl

Cl Cl

OH║CCH2CH2CH2CH3

O

OH║CCH2CH2CH3

O

OH║CH

O

OH║CCH3 – CH2 – CH2 – CH2 – CH2

O

e) f)

2. Draw each of the following compounds:a) propanoic acid b) ethanoic acid

c) 2-methylbutanoic acid d) 3,3-diethyloctanoic acid

e) 4,4-diiodo-2,2-dimethylpentanoic acid f) 3-bromo-4-methylhexanoic acid

Esters3. Name the following compounds:a) b)

c) d)

e) f)

4. Draw each of the following compounds:a) methyl pentanoate b) ethyl octanoate

c) heptyl methanoate d) propyl 3,3-dimethlyoctanoate

e) 3-methylbutyl ethanoate f) 2-methylpropyl methanoate

Chem 20 Organic Chemistry Workbook Jill Agnew8

OH║CCH2CF2CH2F

O

OH║O

C

O║CH

O

O║CCH2CH2CH3

O

CH3 O║CCH2CH2CH2CH3

O

CH2 CH3

O║CCH2CF2CH2F

O

CH2 CH3

CH3O

║CCH3 – CH – CH2

O

CH2 – CH3

CH3

O║CCH3 – CH – CH2

O

CH – CH3

CH3

CH3

CH3

Organic ReactionsFor each of the following reactions:

a. Draw the reaction. b. Give the reaction type. c. Name the organic reactant(s) and product(s) ***10 carbons or less.

1. Propene reacts with solid iodine.

2.

3. 2,3-dimethyl hexane burns in the presence of oxygen gas.

4.

5. 4,4-dimethylhept-2-ene reacts with oxygen.

6.

7.

8. 3-ethyloctanoic acid reacts with ethanol.

9. Benzene reacts with liquid bromine.

10.

11. Cyclohexane reacts with fluorine gas.

12.

13.

14. 3-methylhex-1-yne + oxygen

Chem 20 Organic Chemistry Workbook Jill Agnew9

O2(g) + CH3 – CH2 – CH2 – CH3

OH║O

C + HO – CH3 H2SO4

+ catCH2Cl – CH2 – CH2 – CH2 – CH3

C C H H ≡ 2 Br2 + cat

C5H12 O2(g)+

+ Cl2(g)

OH

cat

H2SO4

15.

16. propyne + fluorine (2 moles)

17.

18. fluoroethane + hydroxide ion

19.

20. ethanol + pentanoic acid

21.

22. propene + hydrogen

23.

24.

25. benzene + iodine

26.

27.

Chem 20 Organic Chemistry Workbook Jill Agnew10

H2SO4

+OH║O

CCH3 – CH2 – CH2 HO – CH3

CH ≡ C – CH3 + F2 cat

n CHCl CHF ‗ cat

H2SO4

butanoic acid + ethanol

+ H – OH cat

cat

+

CH3

I2 cat

CH3 – CH – CH2 – CH2 – CH2 – CH3

OH

cat

cat

H2SO4

+ O2(g)

cat

28.

29. chloroethane + fluorine

30.

31. propane + oxygen

32.

33. propanoic acid + ethanol

34.

35. hexan-2-ol

36.

37. pent-2-ene + bromine

38.

39. + decane + nonane

40.

Chem 20 Organic Chemistry Workbook Jill Agnew11

+ catHI+

I

Cl

+ HCl cat+

cat

cat

H2SO4

cat

OH

n CH2 CCl ‗

catn H2NCH2 CH2NH2 + n HO – CH2 – CH2 – OH

+C30H62 cat+C10H22

+ cat

cat

cat

+C7H16 C5H12 cat

Organic Chemistry Review

1. Name the following compounds:a) b)

c) d)

e) f)

g) h)

i) j)

Chem 20 Organic Chemistry Workbook Jill Agnew12

CH3

CH3

CH3 C CH2 C

Br

CH3

Br Br

Br

OH║O

C

O

OH║CCH2CHBrCH3

F CH3

I

OH

CH3 CH CH CH3

CH3

CH3 CH CH2 CH

C2H5

CH2

CH3

CH3

CH3

CH CH3 CH CH

CH2

CH ‗

CH CH3

CH2

CH3

CH3 CH3

CH2 CH3 C C CH2 ≡

CH2 CH3

k) l)

m) n)

o) p)

q) r)

2. Draw the structure for the following compounds:a) hex-3-yne b) 1-iodo-4-propylcyclopentene

c) 1,2-dichloro-3-fluorocyclobutane d) hexane

e) pentanoic acid f) 3-chlorohexan-1-ol

g) 1,1-diethyl-3,3-dipropylcyclooctane h) tetrachloroethene

i) 3-butyl-4-propylcyclopentene j) 3-methylhexan-2-ol

k) 1,1-dibromo-3-chlorocyclohexane l) ethyne

m) 1,2-dipropylcyclopentene n) nonane

Chem 20 Organic Chemistry Workbook Jill Agnew13

OH║CCH2CH2CH2CH3

O

CH3 CH2 CH2 CH CH3

CH3 CH2 CH2 CH3

H

OH

H

H

H

C C C C

H H

H

H H CH3

C2H5

C CH3 C

CH3

CH ≡ CH CH3

CH3 CH3 CH CH2 CH

C2H5

CH3

CH3

CH3

3. Complete each of the following reactions, name the organic reactant(s) and/or product(s), and give the reaction type.

a)

b)

c)

d)

e)

f)

g)

Chem 20 Organic Chemistry Workbook Jill Agnew14

H2SO4

OH║O

CCH C

H

H

H

H

+ C

H

H

HO C

H

H

H

Cl2 + cat

H

H

OH

H

H

H C C cat

C H

H

H

H F2 + cat

I2 + cat

H

C

H

C C H

H

C

H H

H

H ‗ O2(g) +

n CH2 CHF ‗ cat

h)

i)

j)

6. Make a chart to list the organic compounds that are polar and nonpolar.

7. You have 4 clear colourless solutions all with the same number of carbons: an alkane, an alkene, a carboxylic acid and an alcohol. Design a procedure you could use to correctly label all four solutions.

30-C1.1s design a procedure to identify types of organic compounds

Chem 20 Organic Chemistry Workbook Jill Agnew15

O2(g) +

C C H H ≡ 1 Cl2 + acid

H2SO4

+ H – OH C

H

H

C

H

H

H O║O

CCH C

H

H

H

H