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Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

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Page 1: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education
Page 2: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Carboxylic Acids

A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group .

© 2013 Pearson, Education Inc.

Page 3: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

IUPAC Names of Carboxylic Acids

Page 4: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

IUPAC Names of Carboxylic Acids

The name of the carboxylic acid of benzene, is benzoic acid. The carbon in the carbonyl group is bonded to . carbon 1 in the benzene ring. The ring is numbered to give the lowest possible numbers for any substituents. The prefixes ortho, meta, and para may be used to show the position of one other substituent.

Page 5: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

IUPAC Names of Carboxylic Acids

The prefixes ortho, meta, and para may be used to show the position of one other substituent. Insert diagram of benzoic acid, 4-aminobenzoic acid and 3,4-dichlorobenzoic acid bottom pg 571 with labels.

Page 6: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Common Names of Carboxylic AcidsMany carboxylic acids are still named by their

common names that include prefixes, form, acet, propion, butyr.

When using the common names, the Greek letters alpha (), beta (), and gamma () are assigned to the carbons adjacent to the carboxyl carbon.

Page 7: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Formic Acid

A red ant sting contains formic acid that irritates the skin.

H

C

O

OH

Page 8: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Guide to Naming Carboxylic Acids

Page 9: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

IUPAC Names for Carboxylic Acids

Give the IUPAC and common name for each carboxylic acid.

Page 10: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

IUPAC Names for Carboxylic Acids

Step 1 Identify the longest carbon chain and add “anoic acid” to the end of the base name (for the straight chain acids).

butanoic acid benzoic acid

Page 11: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

IUPAC Names for Carboxylic Acids

Step 2 Give the location and name of each substituent by counting the carboxyl carbon as 1.

a. 2-methylbutanoic acid b. 3-chlorobenzoic acid

2-methylbutyric acid meta-chlorobenzoic acid

Page 12: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Alpha Hydroxy Acids

Alpha hydroxy acids (AHAs)

occur naturally in . fruit, milk, and . sugar cane. are used in skin . care products.

Page 13: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

Give the IUPAC and common names for each of the following.

A.

B.

C.

Page 14: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

A.

B.

C.

Solution

2-Bromobenzoic acid(o-bromobenzoic acid)

2-Methylpropanoic acid

ethanoic acid (acetic acid)

Page 15: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

Give the IUPAC and common names for the following.

A.

B.

C.

Page 16: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Solution Give the IUPAC and common names for the

following.

A.

B.

C.

propanoic acid(propionic acid)

3-Methylbutanoic acid(methylbutyric acid)

3-Bromobenzoic acid(m-bromobenzoic acid)

Page 17: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

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).

© 2013 Pearson Education, Inc.

Page 18: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

Which alcohol would be used to prepare the following?

A. butanoic acid

B. propanoic acid

Page 19: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Solution

(it is the alcohol with the same number of carbons!)

A.

B.

Page 20: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

EstersEsters differ from carboxylic acids by the replacement of

H in the hydroxyl group with an alkyl group.are fragrant components of many fruits, such as

bananas, oranges, and strawberries.Yummy!

Page 21: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Esterification is the reaction of a carboxylic acid and alcohol in the presence of an acid catalyst to produce an ester.

Insert esterification reaction pg 580

Esterification

Page 22: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Acetylsalicylic AcidAspirinis used to relieve pain

and reduce inflammation.

is an ester of salicylic acid

and acetic acid.is derived from the

bark of a willow tree.

Page 23: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Acetylsalicylic AcidIn 1899, Bayer chemical company in Germany produced an ester of salicylic acid and acetic acid, called acetylsalicylic acid (aspirin) that was less irritating to the stomach than salicylic acid.

Page 24: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Methyl SalicylateOil of wintergreenis used to soothe sore muscles.has a pungent, minty odor.is an ester of salicylic acid and

methanol.

Page 25: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Esters in PlantsEsters give flowersand fruits their pleasant fragrances and flavors.

Page 26: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education
Page 27: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Naming Esters

The name of an ester contains the names ofthe alkyl group from the alcohol, andthe carbon chain from the acid with -ate

ending.

Page 28: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Example..

Give the IUPAC and common name of the following ester, responsible for the flavor and odor of pears. A hint is on the next slide…

Page 29: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Example..

Name the group on the oxygen first.

Page 30: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Example..

Name the group on the oxygen first: it is propyl.Now count the number of carbons including the carbonyl carbon that are in the other side of the ester:

O

O

Page 31: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Example..

there are two carbons in the “acid” side of the ester, so the base name uses 2…So this is propyl ethanoate.

O

O

Page 32: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

Name the following ester. Hints are on the next few slides…

Page 33: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

Remember, you want to count the number of carbons on the oxygen first. Since there is one, our “group” is __________

O

O

Page 34: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

Remember, you want to count the number of carbons on the oxygen first. Since there is one, our “group” is methyl…

O

O

Page 35: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

Now you want to focus on the base name which comes from the carbonyl side of the compound…

How many carbons are on this side?

O

O

Page 36: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

How many carbons are on this side? 4So our base name is:

O

O

Page 37: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

How many carbons are on this side? 4So our base name is: butanoate(that’s but for the 4 carbons and anoate

because it is an ester).

O

O

Page 38: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

So the name of the compound is:Methyl butanoate.

O

O

Page 39: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

Here is another ester to try to name...click through the next few slides to work through this stepwise.

Page 40: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

Remember, we name the group on the oxygen first so the first part of the name is…

O

O

Page 41: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

Remember, we name the group on the oxygen first so the first part of the name is…

ethyl

O

O

Page 42: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

Now we look at the number of carbons in the “acid” side :

O

O

Page 43: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

Now we look at the number of carbons in the “acid” side : 3

Since there are three, our base name is…Propanoate. Try to put the whole name together,

then check your answer on the next slide.

O

O

Page 44: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

This is ethyl propanoate.

O

O

Page 45: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

Draw the condensed structural formula of the following ester. Take it one step at a time…

What is the group on the oxygen?

A. Ethyl pentanoate

Page 46: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

What is the group on the oxygen? The ethyl group is on the oxygen.

How many carbons are in the base structure?

A. Ethyl pentanoate

Page 47: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

How many carbons are in the base structure?5 there are 5 carbons since the

base name is pent…Now draw in your ester. I usually start by

drawing the carbonyl with an oxygen attached…then add carbons where needed…

A. Ethyl pentanoate

O

O

Page 48: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

A. Ethyl pentanoate

O

O

Page 49: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

B. Propyl butyrate

So what is the group on the oxygen?

Page 50: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

B. Propyl butyrate

So what is the group on the oxygen? Propyl (3 carbons)

How many carbons are in the base chain?

Page 51: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

B. Propyl butyrate

So what is the group on the oxygen? Propyl (3 carbons)

How many carbons are in the base chain? 4

Page 52: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Learning Check

B. Propyl butyrate

The structure is…

O

O

Page 53: Carboxylic Acids A carboxylic acid contains a a hydroxyl group (–OH) attached to a carboxyl group, which is a carbonyl group. © 2013 Pearson, Education

Thank you for trying this online!I will see you on Wednesday, October 16th.Extra credit opportunities:October 21st: help with National Chemistry

Week activities…N-quad 11:15-1:15October 28th: help with Vietnamese Club

activity…N-2220 11:30-1:00October 31st: help with Halloween activity…

B/C-quad (I think)…11:15-3:00.