Carboxylic Acids and Esters
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10
Learning Check CA 2
Give the IUPAC and common names of the following compound, which is responsible for the flavor and odor of pears. O
||
CH3 — C—O —CH2CH2CH3
Carboxyl Group
Carboxylic acids contain the carboxyl group on carbon 1. O || CH3—COOH CH3 — C—OH = carboxyl group
1NLeabharlann ming Carboxylic Acids
Formula IUPAC alkan -oic acid
11
Solution CA2
O
||
propyl
CH3 — C—O —CH2CH2CH3
propyl ethanoate (IUPAC) propyl acetate (common)
12
Learning Check CA 3
Draw the structure of the following compounds: A. 3-bromobutanoic acid B. Ethyl propionoate
9
Some Esters and Their Names
Flavor/Odor Raspberries HCOOCH2CH3 ethyl methanoate (IUPAC) ethyl formate (common)
Pineapples CH3CH2CH2 COOCH2CH3 ethyl butanoate (IUPAC) ethyl butyrate (common)
3
Learning Check CA1
Give IUPAC and common names: A. CH3COOH CH3 | B. CH3CHCOOH
4
Solution CA 1
A. CH3COOH ethanoic acid; acetic acid CH3 | B. CH3CHCOOH 2-methylpropanoic acid; α-methylpropionic acid
Saponification
• Esters react with a bases • Produce the salt of the carboxylic acid and alcohol O || CH3C—OCH2CH3 + NaOH O ||
CH3C—O– Na+ + HOCH2CH3
17
methanoic acid ethanoic acid propanoic acid
Common prefix – ic acid
formic acid acetic acid propionic acid butyric acid
2
HCOOH CH3COOH CH3CH2COOH
CH3CH2CH2COOH butanoic acid
15
Hydrolysis
• Esters react with water and acid catalyst • Split into carboxylic acid and alcohol O || H+ H — C—O—CH2CH3 + H2O O
||
H — C—OH
+ HO—CH2CH3
16
13
Solution CA 3
A. 3-bromobutanoic acid Br | CH3CHCH2COOH B. Ethyl propionoate O
||
CH3 CH2 COCH2CH3 CH3CH2COOCH2CH3
14
Esterification
• Reaction of a carboxylic acid and alcohol • Acid catalyst O || H+ CH3 — C—OH + HO—CH2CH3 O || CH3 — C—O—CH2CH3 + H2O
20
Solution CA5
A.
O
||
CH3COH O
||
+
HOCH3
B.
CH3CO– K+
+ HOCH3
21
Naming Rules
• Identify longest chain • (IUPAC) Number carboxyl carbon as 1 • (Common) Assign α, β, χ to carbon atoms adjacent to carboxyl carbon CH3 | CH3 — CH—CH2 —COOH IUPAC 3-methylbutanoic acid Common β-methylbutryic acid
5
Properties
• Carboxylic acids are weak acids CH3COOH + H2O • Neutralized by a base CH3COOH + NaOH CH3COO– + H3O+
CH3COO– Na+ + H2O
6
Esters
In and ester, the H in the carboxyl group is replaced with an alkyl group O
18
Solution CA4
O || CH3CH2COH + HOCH3 O || CH3CH2COCH3 + H2O H+
19
Learning Check CA5
What are the organic products when methylacetate reacts with A. Water and an acid catalyst? B. KOH?
||
CH3 — C—O —CH3 = CH3—COO —CH3 ester group
7
Esters in Plants
Esters give flowers and fruits their pleasant fragances and flavors.
8
Naming Esters
• Name the alkyl from the alcohol –O• Name the acid with the C=O with –ate acid alcohol O || methyl CH3 — C—O —CH3 Ethanoate methyl ethanoate (IUPAC) (acetate) methyl acetate (common)
salt of carboxylic acid
Learning Check CA4
Write the equation for the reaction of propionic acid and methyl alcohol in the presence of an acid catalyst.
Learning Check CA 2
Give the IUPAC and common names of the following compound, which is responsible for the flavor and odor of pears. O
||
CH3 — C—O —CH2CH2CH3
Carboxyl Group
Carboxylic acids contain the carboxyl group on carbon 1. O || CH3—COOH CH3 — C—OH = carboxyl group
1NLeabharlann ming Carboxylic Acids
Formula IUPAC alkan -oic acid
11
Solution CA2
O
||
propyl
CH3 — C—O —CH2CH2CH3
propyl ethanoate (IUPAC) propyl acetate (common)
12
Learning Check CA 3
Draw the structure of the following compounds: A. 3-bromobutanoic acid B. Ethyl propionoate
9
Some Esters and Their Names
Flavor/Odor Raspberries HCOOCH2CH3 ethyl methanoate (IUPAC) ethyl formate (common)
Pineapples CH3CH2CH2 COOCH2CH3 ethyl butanoate (IUPAC) ethyl butyrate (common)
3
Learning Check CA1
Give IUPAC and common names: A. CH3COOH CH3 | B. CH3CHCOOH
4
Solution CA 1
A. CH3COOH ethanoic acid; acetic acid CH3 | B. CH3CHCOOH 2-methylpropanoic acid; α-methylpropionic acid
Saponification
• Esters react with a bases • Produce the salt of the carboxylic acid and alcohol O || CH3C—OCH2CH3 + NaOH O ||
CH3C—O– Na+ + HOCH2CH3
17
methanoic acid ethanoic acid propanoic acid
Common prefix – ic acid
formic acid acetic acid propionic acid butyric acid
2
HCOOH CH3COOH CH3CH2COOH
CH3CH2CH2COOH butanoic acid
15
Hydrolysis
• Esters react with water and acid catalyst • Split into carboxylic acid and alcohol O || H+ H — C—O—CH2CH3 + H2O O
||
H — C—OH
+ HO—CH2CH3
16
13
Solution CA 3
A. 3-bromobutanoic acid Br | CH3CHCH2COOH B. Ethyl propionoate O
||
CH3 CH2 COCH2CH3 CH3CH2COOCH2CH3
14
Esterification
• Reaction of a carboxylic acid and alcohol • Acid catalyst O || H+ CH3 — C—OH + HO—CH2CH3 O || CH3 — C—O—CH2CH3 + H2O
20
Solution CA5
A.
O
||
CH3COH O
||
+
HOCH3
B.
CH3CO– K+
+ HOCH3
21
Naming Rules
• Identify longest chain • (IUPAC) Number carboxyl carbon as 1 • (Common) Assign α, β, χ to carbon atoms adjacent to carboxyl carbon CH3 | CH3 — CH—CH2 —COOH IUPAC 3-methylbutanoic acid Common β-methylbutryic acid
5
Properties
• Carboxylic acids are weak acids CH3COOH + H2O • Neutralized by a base CH3COOH + NaOH CH3COO– + H3O+
CH3COO– Na+ + H2O
6
Esters
In and ester, the H in the carboxyl group is replaced with an alkyl group O
18
Solution CA4
O || CH3CH2COH + HOCH3 O || CH3CH2COCH3 + H2O H+
19
Learning Check CA5
What are the organic products when methylacetate reacts with A. Water and an acid catalyst? B. KOH?
||
CH3 — C—O —CH3 = CH3—COO —CH3 ester group
7
Esters in Plants
Esters give flowers and fruits their pleasant fragances and flavors.
8
Naming Esters
• Name the alkyl from the alcohol –O• Name the acid with the C=O with –ate acid alcohol O || methyl CH3 — C—O —CH3 Ethanoate methyl ethanoate (IUPAC) (acetate) methyl acetate (common)
salt of carboxylic acid
Learning Check CA4
Write the equation for the reaction of propionic acid and methyl alcohol in the presence of an acid catalyst.