1. 1 C hapter 13 Organic Compounds with Oxygen and Sulfur 13.1 Alcohols, Ethers, and Thiols Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings

2. 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. wateralcohol phenol Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings

3. 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. FormulaIUPACCommon Name CH 4 methane CH 3 ─OH methanol methyl alcohol CH 3 ─CH 3 ethane CH 3 ─CH 2 ─OH ethanol ethyl alcohol

4. 4 More Names of Alcohols IUPAC names for longer chains number the chain from the end nearest the -OH group. CH 3 ─CH 2 ─CH 2 ─OH 1-propanol OH │ CH 3 ─CH─CH 2 ─CH 3 2-butanol CH 3 OH │ │ CH 3 ─CH─CH 2 ─CH 2 ─CH─CH 3 5-methyl-2-hexanol 6 5 4 3 2 1

5. 5 Some Typical Alcohols OH | “rubbing alcohol”CH 3 —CH—CH 3 2-propanol (isopropyl alcohol) antifreeze HO—CH 2 —CH 2 —OH 1,2-ethanediol (ethylene glycol) OH | glycerolHO—CH 2 —CH—CH 2 —OH 1,2,3-propanetriol

6. 6 Learning Check Name the following compounds. 1. CH 3 —CH 2 —CH 2 —CH 2 —OH OH CH 3 | | 2. CH 3 —CH—CH—CH 2 —CH 3 3.

7. 7 Solution 1. CH 3 —CH 2 —CH 2 —CH 2 —OH 1-butanol OH CH 3 | | 2. CH 3 —CH—CH—CH 2 —CH 3 3-methyl-2-pentanol 3. cyclopentanol

8. 8 Phenols in Medicine Phenol is the IUPAC name for benzene with a hydroxyl group. is used in antiseptics and disinfectants. phenol resorcinol 4-hexylresorcinol

9. 9 Derivatives of Phenol Compounds of phenol are the active ingredients in the essential oils of cloves, vanilla, nutmeg, and mint.

10. 10 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. 3-chlorophenol 4-bromophenol 3 4 1 1

11. 11 Write the structure of each of the following. A. 3-pentanol B. ethyl alcohol C. 4-methylphenol Learning Check

12. 12 Solution Write the structure of the following. A. 3-pentanol OH | CH 3 —CH 2 —CH—CH 2 —CH 3 B. ethyl alcohol CH 3 —CH 2 —OH C. 4-methylphenol OH CH 3

13. 13 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 2 groups 3 groups H CH 3 CH 3 | | | CH 3 —C—OH CH 3 —C—OH CH 3 —C—OH | | | H H CH 3 Classification of Alcohols

14. 14 Classify each alcohol as 1) primary, 2) secondary, or 3) tertiary. OH | A. CH 3 —CH—CH 2 —CH 3 B. CH 3 —CH 2 —CH 2 —OH OH | C. CH 3 —CH 2 —C—CH 2 —CH 3 | CH 3 Learning Check

15. 15 OH | A. CH 3 —CH—CH 2 —CH 3 secondary B. CH 3 —CH 2 —CH 2 —OH primary OH | C. CH 3 —CH 2 —C—CH 2 —CH 3 tertiary | CH 3 Solution

16. 16 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 © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings

17. 17 Thiols often have strong odors. are used to detect gas leaks. are found in onions, oysters, and garlic.

18. 18 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. CH 3 ─O─CH 3 CH 3 ─CH 2 ─O─CH 3 dimethyl ether ethyl methyl ether

19. 19 Learning Check Write the structure of the following. A. 3-pentanol B. diethyl ether

20. 20 Solution OH | A. 3-pentanolCH 3 ─CH 2 ─CH─CH 2 ─CH 3 B. diethyl ether CH 3 ─CH 2 ─O─CH 2 ─CH 3

21. 21 Ethers as Anesthetics Anesthetics inhibit pain signals to the brain. like diethyl ether CH 3 ─CH 2 ─O─CH 2 ─CH 3 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─HH─C─C─O─C─H │ │ │ │ │ │ F F F H F H Ethane(enflurane) Penthrane

22. 22 MTBE Methyl tert-butyl ether CH 3 │ CH 3 ─O─C─CH 3 │ CH 3 is second in production of organic chemicals. is an additive used to improve gasoline performance. use is questioned since the discovery that MTBE has contaminated water supplies.