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Carboxylic Acids and Esters The functional group of carboxylic acids is the carboxyl group.

Carboxylic Acids and Esters The functional group of carboxylic acids is the carboxyl group. Naming Carboxylic Acids Find the longest carbon chain that contains the –COOH group. Drop the –e from the end of the alkane name and substitute –oic acid.

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Carboxylic Acids and Esters The functional group of carboxylic acids is the carboxyl group.

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  1. Carboxylic Acids and Esters The functional group of carboxylic acids is the carboxyl group.

  2. Naming Carboxylic Acids Find the longest carbon chain that contains the –COOH group. Drop the –e from the end of the alkane name and substitute –oic acid. Number the longest chain. Carbon number 1 is the carbonyl carbon. Name and number other substituents.

  3. Example:

  4. Physical Properties • The carboxyl group contains three polar covalent bonds; C=O, C-O, and O-H. • The polarity of these bonds determines the major physical properties of carboxylic acids.

  5. PHYSICAL PROPERTIES OF CARBOXYLIC ACIDS • Low molecular weight carboxylic acids are liquids at room temperature and have characteristically sharp or unpleasant odors. • The –COOH group is very polar. Hydrogen bonding between –COOH groups creates dimers (two identical molecules bonded together). • This gives carboxylic acids high boiling points (greater than alcohols).

  6. PHYSICAL PROPERTIES, cont. • –COOH groups can hydrogen bond with water. If the hydrophobic –R group is not too large, carboxylic acids are very water soluble.

  7. Physical Properties • Carboxylic acids are more soluble in water than are alcohols, ethers, aldehydes, and ketones of comparable molecular weight.

  8. Esters Esters are formed by reacting a carboxylic acid and an alcohol.

  9. Carboxylic Esters The ester functional group with the ester linkage between the carbonyl carbon and the oxygen atom:

  10. Examples:

  11. Naming Esters The first word of the name of an ester is the name of the alkyl or aromatic group (R') contributed by the alcohol. The second word is the carboxylic acid name, with the –ic acid ending changed to –ate.

  12. Naming Esters, cont.

  13. Ester Reactions Hydrolysis – break apart with water.

  14. Ethyl ethanoate Ethanoic acid ethanol Specific Examples:

  15. Learning check 5.8

  16. Esters, cont. Polyesters – polymers made by the esterification process. An example of condensation polymerization. n(monomers)  (polymer)n + nH2O

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