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Chapter 16 Carboxylic Acids and Esters

Chapter 16 Carboxylic Acids and Esters. 16.1 Carboxylic Acids. Carboxylic Acids. A carboxylic acid contains a carboxyl group , which is a carbonyl group (C═O) attached to a hydroxyl group ( — OH) has the carboxyl group on carbon 1. Some Typical Carboxylic Acids.

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Chapter 16 Carboxylic Acids and Esters

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  1. Chapter 16 Carboxylic Acids and Esters 16.1Carboxylic Acids

  2. Carboxylic Acids A carboxylic acid • contains a carboxyl group,which is a carbonyl group (C═O) attached to a hydroxyl group (—OH) • has the carboxyl group on carbon 1

  3. Some Typical Carboxylic Acids

  4. Guide to Naming Carboxylic Acids

  5. Example of Writing IUPAC Names for Carboxylic Acids To write the IUPAC names of a carboxylic acid STEP 1 Replace the e in the alkane name with oic acid. CH4 Methane HCOOH Methanoic acid CH3—CH3 Ethane CH3—COOH Ethanoic acid STEP 2Locate and name substituents, counting from the carboxyl carbon as carbon 1.

  6. Common Names for Simple Carboxylic Acids The common names of simple carboxylic acids • are formic acid (1C), acetic acid (2C), propionic acid (3C), and butyric acid (4C). • Examples: HCOOH CH3—COOH Methanoic acid Ethanoic acid (formic acid) (acetic acid)

  7. Common Names for Carboxylic Acids 3-Methylbutanoic acid (-methylbutryic acid) The common names of carboxylic acids • use letters , , or  to indicate locations of substituents

  8. Alpha Hydroxy Acids Alpha hydroxy acids (AHAs) • occur naturally in fruit, milk, and sugarcane • are used in skin care products

  9. Common Carboxylic Acids Methanoic acid (formic acid) Ethanoic acid (acetic acid)

  10. Aromatic Carboxylic Acids Benzoic acid • is the aromatic carboxylic acid • locates substituents by assigning 1 to the carbon attached to the carboxyl group • has common names that assign prefixes ortho-, meta-, and para- for 2 substituents ortho (o)1, 2 location meta (m) 1, 3 location para (p) 1, 4 location

  11. Aromatic Carboxylic Acids (continued)

  12. Learning Check Give the IUPAC and common names for each of the following: A. B. C.

  13. Solution Give the IUPAC and common names for each of the following: A. B. C. Ethanoic acid (acetic acid) 2-Methylpropanoic acid (-methylpropionic acid) 2-Bromobenzoic acid (o-bromobenzoic acid)

  14. Learning Check Give the IUPAC and common names for the following: A. B. C.

  15. Solution A. Propanoic acid (propionic acid) 3-Methylbutanoic acid (-methylbutyric acid) B. 3-Bromobenzoic acid (m-bromobenzoic acid) C.

  16. Preparation of Carboxylic Acids Carboxylic acids are prepared • by oxidizing primary alcohols or aldehydes • from the oxidation of ethanol, which produces ethanoic acid (acetic acid)

  17. Learning Check What alcohol would be used to prepare the following: 1. Butanoic acid 2. Propanoic acid

  18. Solution What alcohol would be used to prepare the following: [O] [O] 1. Butanol butanal butanoic acid [O] [O] 2. 1-Propanol propanal propanoic acid

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