1. PROBLEMS FOR CH 13

2. Learning Check Give the IUPAC name for each of the following.
CH3—CH2—CH2—CH2—OH B. 2

3. Learning Check Give the IUPAC name for each of the following.
Step 1 Name the longest carbon chain attached to
the −OH group by replacing the -e in the
corresponding alkane name with -ol . B.
pentanol
butanol
CH3—CH2—CH2—CH2—OH 3

4. Learning Check Give the IUPAC name for each of the following.
Step 2 Number the chain starting at the end closer
to the −OH group.
pentanol
butanol
CH3—CH2—CH2—CH2—OH B. 4

5. Learning Check Give the IUPAC name for each of the following.
Step 3 Give the location and name of each
substituent relative to the −OH group.
3-methyl-1-pentanol
butanol
CH3—CH2—CH2—CH2—OH B. 5

6. Learning Check Draw the condensed structural formula of the following.
A. 3-Pentanol
B. Propyl alcohol
C. 3-Methylcyclohexanol 6

7. Solution Draw the condensed structural formula of the following.
A. 3-Pentanol
B. Propyl alcohol CH3—CH2—CH2—OH
C. 3-Methylcyclohexanol 7

8. Learning Check
Name the following phenol. 8

9. Solution Name the following phenol. Step 1 Name an aromatic alcohol
as a phenol.
Step 2 Number the chain starting
at the end closer to the
−OH group. (In phenol,
carbon number one is the −OH group.)
Step 3 Give the location and name of each
substituent relative to the −OH group.
3-Chloro-phenol
-phenol 9

10. Learning Check Draw the condensed structural formula of the following.
A. 3-Pentanol
B. Ethyl alcohol
C. p-Methylphenol 10

11. Solution Draw the condensed structural formula of the following.
A. 3-Pentanol
B. Ethyl alcohol CH3—CH2—OH
C. p-Methylphenol 11

12. Learning Check Draw the condensed structural formula of each of the
following compounds.
A. 2-Butanethiol
B. 2-Methyl-1-butanol 12

13. Solution Draw the condensed structural formula of each of the
following compounds.
A. 2-Butanethiol
B. 2-Methyl-1-butanol 13

14. Learning Check
Name each of the following compounds. 14

15. Solution Name each of the following compounds. 2-Butanol
3-Methyl-1-pentanol
1-Propanethiol 15

16. Learning Check Give the IUPAC name for the following.
CH3—O—CH2—CH2—CH2—CH2—CH3 16

17. Solution Give the IUPAC name for the following.
CH3—O—CH2—CH2—CH2—CH2—CH3
Step 1 Write the alkane name of the longer
carbon chain.
methoxy group longer carbon chain
Step 2 Name the oxygen and smaller alkyl group
as a substituent called an alkoxy group. 17

18. Solution Give the IUPAC name for the following.
CH3—O—CH2—CH2—CH2—CH2—CH3
Step 3 Number the longer carbon chain from the
end nearer the alkoxy group and give its
location.
1-methoxypentane 18

19. Learning Check
Name each of the following. A. B. 19

20. Solution Name each of the following. A. Methoxy cyclopentane
(cyclopentyl methyl ether)
B ,4-Dioxane 20

21. Learning Check Draw the condensed structural formula of each of the
following compounds.
A. 1-Ethoxypropane
B. Ethyl methyl ether
C. 2-Methoxybutane 21

22. Solution Draw the condensed structural formula of each of the
following compounds.
A. 1-Ethoxypropane
CH3—CH2—O—CH2—CH2—CH3
B. Ethyl methyl ether
CH3—CH2—O—CH3
C. 2-Methoxybutane 22

23. Learning Check
Classify each of the following alcohols as primary, secondary, or tertiary.
A. isopropyl alcohol, 2-propanol
B. 1-butanol C. D. 23

24. Solution
Classify each of the following alcohols as primary, secondary, or tertiary.
A. isopropyl alcohol, 2-propanol secondary
B. 1-butanol primary
C tertiary
D. secondary 24

25. Learning Check Which compound would have the higher boiling
point, ethyl methyl ether or 1-propanol? Explain. 25

26. Solution Which compound would have the higher boiling
point, ethyl methyl ether or 1-propanol? Explain.
1-propanol has 3 carbon atoms, and can form hydrogen bonds with water giving it a higher boiling point.
Ethyl methyl ether also has 3 carbons, but forms fewer hydrogen bonds with water due to its structure. 26

27. Learning Check
Which compound would be more soluble in water, ethanol or 2-pentanol? Explain. 27

28. Solution
Which compound would be more soluble in water, ethanol or 2-pentanol? Explain.
Ethanol has 2 carbon atoms in its chain. It is more soluble than pentanol with 5 carbons.
The longer the alkyl chain, the less soluble the alcohol in water. 28

29. Learning Check
Write the equations for the reactions when 2-propanol undergoes _______.
A. combustion
B. dehydration 29

30. Solution
Write the equations for the reactions when 2-propanol undergoes _______.
A. combustion
B. dehydration 30

31. Learning Check Match the products with the reaction of
Reaction 1: H+, heat
Reaction 2: [O]
Reaction 3: O2, heat 31

32. Solution Match the products with the reaction of
Reaction 1: H+, heat (dehydration)
Reaction 2: [O], (oxidation)
Reaction 3: O2, heat, (combustion) 32

33. Learning Check
Select the product from the oxidation of _______.

34. Solution Select the product from the oxidation of _______.
Answer is B. 34