1. CHAPTER 1.4 Alcohols, Ethers and Thiols
Learning Objective:
Learn the nomenclature and uses of Alcohols, Ethers and Thiols.
Keywords:
Alcohol, Primary Alcohol, Secondary Alcohol, Tertiary Alcohol, Phenol, Thiols, Ether

2. Alcohols
An alcohol contains a hydroxyl group (—OH) attached to a carbon chain.
A phenol contains a hydroxyl group (—OH) attached to a benzene ring.
water alcohol phenol
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Publishing as Benjamin Cummings

3. Naming Alcohols The names of alcohols
in IUPAC replace the -e with -ol.
with common names use the name of the alkyl group
followed by alcohol.
Formula IUPAC Common Name
CH4 methane
CH3─OH methanol methyl alcohol
CH3─CH3 ethane
CH3─CH2─OH ethanol ethyl alcohol

4. Names the following Alcohols
IUPAC names for longer chains - number the chain from the end nearest the -OH group.
CH3─CH2─CH2─OH OH │
CH3─CH─CH2─CH3
CH OH
│ │
CH3─CH─CH2─CH2─CH─CH3

5. More Names of Alcohols - Answers
IUPAC names for longer chains - number the chain from the end nearest the -OH group.
CH3─CH2─CH2─OH propanol OH │
CH3─CH─CH2─CH butanol
CH OH
│ │
CH3─CH─CH2─CH2─CH─CH methyl-2-hexanol

6. Some Typical Alcohols | “rubbing alcohol” CH3—CH—CH3
2-propanol (isopropyl alcohol)
antifreeze HO—CH2—CH2—OH
1,2-ethanediol (ethylene glycol)
glycerol HO—CH2—CH—CH2—OH
1,2,3-propanetriol

7. End Task Name the following compounds. 1. CH3—CH2—CH2—CH2—OH OH CH3
| |
2. CH3—CH—CH—CH2—CH3 3.
2 minutes
End

8. Solution OH CH3 | | 2. CH3—CH—CH—CH2—CH3 3-methyl-2-pentanol
1. CH3—CH2—CH2—CH2—OH 1-butanol
OH CH3
| |
2. CH3—CH—CH—CH2—CH methyl-2-pentanol
cyclopentanol

9. Phenols in Medicine Phenol
is the IUPAC name for benzene with a hydroxyl group.
is used in antiseptics and disinfectants.
phenol resorcinol or benzenediol hexylresorcinol

10. Derivatives of Phenol
Compounds of phenol are the active ingredients in the essential oils of cloves, vanilla, nutmeg, and mint.

11. Naming Phenols To name a phenol
with two substituents, assign C-1 to the carbon attached to the –OH.
number the ring to give the lowest numbers. 1 1 3 4
3-chlorophenol bromophenol

12. End Task Write the structure of each of the following. A. 3-pentanol
B. ethyl alcohol
C methylphenol
2 minutes
End

13. Solution Write the structure of the following. A. 3-pentanol OH |
CH3—CH2—CH—CH2—CH3
B. ethyl alcohol CH3—CH2—OH
C. 4-methylphenol O H C 3

14. Classification of Alcohols
Classification of alcohols is
determined by the number of alkyl groups attached to the carbon bonded to the hydroxyl.
primary (1°), secondary (2°), or tertiary(3).
Primary (1º) Secondary (2º) Tertiary (3º) 1 group groups 3 groups H CH CH | | |
CH3—C—OH CH3—C—OH CH3—C—OH | | | H H CH3

15. End Task 1) primary, 2) secondary, or 3) tertiary. OH |
Classify each alcohol as
1) primary, 2) secondary, or 3) tertiary. OH |
A. CH3—CH—CH2—CH3
B. CH3—CH2—CH2—OH
C. CH3—CH2—C—CH2—CH3
CH3
2 minutes
End

16. Solution | A. CH3—CH—CH2—CH3 secondary B. CH3—CH2—CH2—OH primary
C. CH3—CH2—C—CH2—CH3 tertiary
CH3

17. Thiols Thiols are carbon compounds that contain a –SH group.
are named in the IUPAC system by adding thiol to the alkane name of the longest carbon chain.
Copyright © by Pearson Education, Inc.
Publishing as Benjamin Cummings

18. Thiols Thiols often have strong smells. are used to detect gas leaks.
are found in onions, oysters, and garlic.

19. Ethers An ether contains an ─O─ between two carbon groups.
has a common name that gives the alkyl names of the attached groups followed by ether.
CH3─O─CH3 CH3─CH2─O─CH3
dimethyl ether ethyl methyl ether

20. End Task Write the structure of the following. A. pentyl propyl ether
B. diethyl ether
2 minutes
End

21. Solution
A. pentyl propyl ether
B. diethyl ether CH3─CH2─O─CH2─CH3

22. Ethers as Anesthetics Anesthetics inhibit pain signals to the brain.
like diethyl ether CH3─CH2─O─CH2─CH3 were used for over a century, but caused nausea and were flammable.
developed by the 1960’s were nonflammable.
Cl F F Cl F H
│ │ │ │ │ │
H─C─C─O─C─H H─C─C─O─C─H
F F F H F H
Ethane(enflurane) Penthrane

23. TASK
Answer the questions on the handout. If you don’t finish it in class, do it for homework please 