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General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.1 Chapter 13 Alcohols, Phenols, and Thiols 13.1 Alcohols, Phenols, and Thiols
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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
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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
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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.
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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
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General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. Guide to Naming Alcohols 6
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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
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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.
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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
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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.
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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
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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)
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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
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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
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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:
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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
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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)
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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.
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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
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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:
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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
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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
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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
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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
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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:
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General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.26 Learning Check Name each of the following compounds:
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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
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