1. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.1 Chapter 13 Alcohols, Phenols, and Thiols 13.1 Alcohols, Phenols, and Thiols

2. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.2 Alcohols and Phenols An alcohol contains  a hydroxyl group (—OH) attached to a carbon chain A phenol contains  a hydroxyl group (—OH) attached to a benzene ring

3. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. Alcohols are classified  by the number of alkyl groups attached to the carbon bonded to the hydroxyl  as primary (1°), secondary (2°), or tertiary(3) 3 Classification of Alcohols

4. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.4 Classify each alcohol as P) primary, S) secondary, or T) tertiary. Learning Check B. CH 3 —CH 2 —CH 2 —OH A. C.

5. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.5 Solution B. CH 3 —CH 2 —CH 2 —OH A. C. (S) secondary (P) primary (T) tertiary

6. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. Guide to Naming Alcohols 6

7. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.7 Naming Alcohols The names of alcohols  in IUPAC system replace -e of alkane name with -ol  that are 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

8. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.8 More Names of Alcohols In IUPAC names for longer carbon chains, the chain is numbered from the end nearer the –OH group.

9. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.9 Some Typical Alcohols “Rubbing alcohol”: 2-Propanol (isopropyl alcohol) Antifreeze: 1,2-Ethanediol (ethylene glycol) Glycerol: 1,2,3-Propanetriol

10. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.10 Learning Check Give the IUPAC name for each of the following: A. CH 3 —CH 2 —CH 2 —CH 2 —OH B. C.

11. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.11 Solution A. CH 3 —CH 2 —CH 2 —CH 2 —OH 1-butanol STEP 1 Name the longest chain attached to  OH: butanol STEP 2 Number the chain from the end closer to  OH: CH 3 —CH 2 —CH 2 —CH 2 —OH 4 3 2 1 STEP 3 Name alcohol: 1-butanol

12. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. B. 3-methyl-2-pentanol STEP 1 Name the longest chain attached to  OH: pentanol STEP 2 Number the chain from the end closer to  OH: 1 2 3 4 5 STEP 3 Name alcohol and any substituents: 3-methyl-2-pentanol 12 Solution (continued)

13. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.13 Solution (continued) C. cyclopentanol STEP 1 Name the longest chain attached to  OH: cyclopentanol STEP 2 Number the chain from the end closer to  OH: (not necessary with one substituent) STEP 3 No substituents other than alcohol STEP 4 Name a cyclic alcohol as cycloalkanol: cyclopentanol

14. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.14 Draw the condensed structural formula of the following: A. 3-Pentanol B. Propyl alcohol C. 3-Methylcyclohexanol Learning Check

15. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.15 Solution Draw the condensed structural formula of the following: A. 3-Pentanol: B. Propyl alcohol: CH 3 —CH 2 —CH 2 —OH C. 3-Methylcyclohexanol:

16. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.16 Phenols in Medicine Phenol  is the IUPAC name for benzene with a hydroxyl group  is used in antiseptics and disinfectants Phenol Resorcinol 4-Hexylresoricinol

17. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.17 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  use prefixes o, m, and p for common names Phenol 3-chlorophenol 4-bromophenol (m-chlorophenol) (p-bromophenol)

18. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.18 Derivatives of Phenol  Compounds of phenol are the active ingredients in the essential oils of cloves, vanilla, nutmeg, and mint.

19. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.19 Draw the condensed structural formula of the following: A. 3-Pentanol B. Ethyl alcohol C. p-Methylphenol Learning Check

20. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.20 Solution Draw the condensed structural formula of the following: A. 3-Pentanol: B. Ethyl alcohol: CH 3 —CH 2 —OH C. p-Methylphenol:

21. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.21 Thiols  are organic compounds that contain a –SH group  are named in the IUPAC system by adding thiol to the alkane name of the longest carbon chain

22. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.22  In thiols with long carbon chains, the chain is numbered to locate the  SH group. Naming Thiols

23. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.23 Sources of Thiols Thiols  often have strong odors  are used to detect gas leaks  are found in onions, oysters, and garlic

24. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.24 Learning Check Draw the condensed structural formula of each of the following compounds: A. 2-Butanethiol B. 2-Methyl-1-butanol

25. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.25 Solution Draw the condensed structural formula of each of the following compounds: A. 2-Butanethiol: B. 2-Methyl-1-butanol:

26. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.26 Learning Check Name each of the following compounds:

27. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.27 Solution Name each of the following compounds: 1-Propanethiol 3-Methyl-1-pentanol 2-Butanol