Carboxylic Acids

EXAM 1 - RESULTS

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• High score = 100 (2 people)

• Median score = 62

• Average score = 63

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13 –1

The Hardest Problems

9. Halogenated ethers are usually less flammable than nonhalogenated ethers.

10. Dissolving an amine in water produces an acidic solution.

CH2 –CH3

CH3-CH2–CH-CH3

|

CH3

CH3-CH2–CH2-CH

\

CH3

/

1 2

12. Compound 1 is properly termed: (a) 3-methylpentane, (b) 3-ethylbutane, (c)

2-ethylbutane, (d) 1-methyl,1-ethylpropane.

13. Compound 2 is properly termed: (a) 1,1-dimethylbutane,

(b) 2-methylpentane, (c) 4-methylpentane, (d) 4,4-dimethylbutane.

16. Different shapes of the same compound are called: (a) isomers, (b) monomers, (c) polymers, (d) conformations.

23. How many different products result from the monochorination of

CH

3

-CH

2

-CH

2

-CH

3

? (a) just 1, (b) 2, (c) 3, (d) 4.

24. How many different products result from the monochorination of

CH

3

-CH

2

-CH

2

-CH

2

-CH

3

? (a) just 1, (b) 2, (c) 3, (d) 4.


13 –2

The Hardest Problems (cont’d)

44. The addition reaction R-S-S-R + H

2

(c) H2C=O, (d) HRS-SRH.

yields: (a) 2R-SH, (b) R-O-R-SH,

O

║

R—C—OH

(c)

48. Formula (c) represents: (a) an organic acid, (b) a ketone, (c) an alcohol,

(d) an aldehyde .


13 –3

The Rules for Boiling Points

• The boiling points of compounds depend on how strongly they stick together: The more strongly they stick together, the higher the boiling point (the more heat it takes to rip them apart).

• There are two main forces that hold molecules together:

Hydrogen bonds

These require both positive hydrogens (from O-H or N-H bonds) and electron lone pairs (found mainly on O and N atoms)

London forces (see Chapter 6, pages 169-170)

-Bigger molecules have stronger intermolecular forces, and higher boiling points, other things being equal.

-These forces are very short-range, so this also depends on how close the molecules can get together. The more branches in an alkane, the harder it is for them to get close. Branched alkanes thus have lower densities and lower boiling points (see page 257).


13 –4

Recent News

• A recent report asserts that dogs have been trained to detect cancer by sniffing samples taken from the breaths of healthy persons and cancer victims.

• Dogs can detect odors at the low parts per billion (ppb) level.

• It is claimed that tumor cells emit different chemicals-alkanes and benzene derivatives--than healthy cells.

• Reference: The New York Times , January 17, 2006, p. D5.


13 –5

ADVICE

• It is very important that you begin to study the material as early as possible.

• Working the practice problems and answering the practice questions is absolutely essential.


13 –6

Chapter Thirteen

Hydrocarbon

Derivatives II:

Carbon Oxygen

Double Bonds

Functional Groups Containing the

Carbon-Oxygen Double Bond


13 –8

13.1 The Carbonyl Group

• A Carbonyl Group consists of a carbon atom and an oxygen atom joined by a double bond.

This is by definition a carbonyl group (C=O).

O » Acetone for example contains a carbonyl group.

H

3

C CH

3

Pronounced carbon-EEL

• Carbonyl groups are strongly polarized, with a partial positive charge on carbon and partial negative charge on oxygen.


13 –9

Because oxygen is more electronegative than carbon, it pulls the electrons in the double bond toward oxygen creating a partial negative charge on oxygen and a partial positive charge on the carbonyl carbon atom. Much of the reactivity of carbonyl groups results from this polarization.

E.N. = 3.5

E.N. = 2.5


13 –10

• The polarity of the carbonyl group contributes to its reactivity.

• The carbonyl carbon is bonded to oxygen and two other atoms. The bond angles between the three components on carbon are 120 o or close to it.

• Carbonyl compounds are broadly divided into two groups: (1) aldehydes and ketones are in one group and (2) the second group contains carboxylic acids, esters, and amides.


13 –11


13 –12

Structural Characteristics and

Naming of Aldehydes


13 –13

An aldehyde is a compound that has at least one hydrogen atom attached to the carbon atom of a carbonyl group.

O

H

O

CH

3 an aldehyde a ketone

R

O

H

The R group in an aldehyde can be

H, alkyl, or aryl.


13 –14

Some Common Aldehydes

• Formaldehyde, H(C=O)H: Toxic but useful. It kills viruses, fungi, and bacteria. It is used in disinfecting and sterilizing equipment.

• Acetaldehyde CH

3

(C=O)H: Sweet smelling and narcotic.

Present in ripe fruits, especially in apples. It is less toxic than formaldehyde.

• Benzaldehyde Ph(C=O)H: Oil of almonds; used to make dyes, perfumes, and specific flavors.


13 –15

Some Common Aldehydes

Some aldehydes are present in nuts and spices .

O

H

H

O

H

H

HO

O

CH

3

O

H oil of almonds cinnamaldehyde vanillin


13 –16

Naming Aldehydes

The simplest aldehydes are known by their common names, formaldehyde, acetaldehyde, benzaldehyde, and so on.

To name aldehydes systematically in the

IUPAC system, the final –e of the name of the alkane is replaced by –al.


13 –17

When a compound contains more than one type of functional group, the suffix for only one of them can be used as the ending of the name. The IUPAC rules define priorities that specify which suffix should be used:

1. Carboxylic acid

2. Aldehyde

3. Ketone

4. Alcohol

5. Amine

6. Alkene

7. alkyne

Remember that alkoxy (ether), halogen (halide), and alkyl

Groups are treated as substituents and listed in alphabetical order.


13 –18

1. To name an aldehyde, select the longest chain which contains the aldehyde functional group.

2. Then name the parent chain by changing the -e ending to -al.

3. Number the parent chain starting with 1 for the aldehyde carbon atom.

4. Determine the identity of the substituents, and add this information to the front of the parent chain name.

OH O

H pentane  pentanal pentanal  3-hydroxypentanal


Note that the aldehyde is the primary functional group and so this is named as an aldehyde and not as an alcohol.

13 –19

Properties and Reactions of Aldehydes


13 –20

Properties of Aldehydes and Ketones

• The polarity of the carbonyl group makes aldehydes and ketones moderately polar compounds. As a result, they have boiling points higher than alkanes and are reactive.

• Aldehydes and ketones do not form hydrogen bonds to each other, however, they form hydrogen bonds with water using the lone pairs of electrons on oxygen.

• Aldehydes and ketones have boiling points intermediate between alkanes and alcohols of similar size.


13 –21

Aldehydes and ketones are soluble in common organic solvents, and those with fewer then five carbons are also soluble in water.


13 –22

Rules for Solubility

• “Like dissolves like.” This means that polar compounds dissolve best in polar solvents (like water and alcohols) and nonpolar compounds dissolve best in nonploar solvents (like hexane and benzene).

• Some compounds, like alcohols, have a polar part (the -OH group) and a nonpolar part (the hydrocarbon portion). Solubility in water depends on which part dominates. Alcohols with a large

“organic” (hydrocarbons) portion are not very soluble in water.

• Carbonyl compounds will be soluble in water if their hydrocarbon portion is not too large. The water can form hydrogen bonds to the electron lone pairs on the oxygen. But if the organic portion is too large, solubility is decreased.

• Acetone, CH

3

-(C=O)-CH

3

, is an excellent solvent for both polar and nonpolar compounds.


13 –23

--Simple ketones are excellent solvents because they dissolve both polar and nonpolar compounds;

(CH

3

HC=O) is an example.

acetone

--The lower boiling aldehydes and ketones are flammable.

--The simple ketones have low toxicity, however, many simple aldehydes are toxic because they react with proteins and other biomolecules; example formaldehyde .


13 –24

Oxidation of Aldehydes

• Primary alcohols can be oxidized to aldehydes and secondary alcohols to ketones.

• Aldehydes can be further oxidized to carboxylic acids.

• Since ketones cannot be further oxidized, application with a mild oxidizing agent can be used as a test to distinguish between aldehydes and ketone.


13 –25

Primary alcohol:

CH

3

CH

2

OH + [O]



CH

3

CH=O + H

2

O [oxidation to an aldehyde]

CH

3

CH=O + [O]



CH

3

COOH + H

2

O [further oxidation to an organic acid]

Secondary alcohol:

|

OH

CH

3

CH-CH

3

+ [O]



CH

3

(C=O)CH

3

[oxidation to a ketone]

+ H

2

O

The ketone cannot be further oxidized.


13 –26

A positive Tollens test for aldehydes involves the formation of a silver mirror. (a) An aqueous solution of ethanal is added to a solution of silver nitrate in aqueous ammonia and stirred. (b) The solution darkens as ethanal is oxidized to ethanoic acid, and

Ag +1 ion is reduced to silver. (c) The inside of the beaker becomes coated with metallic silver.

The aldehyde is oxidized and the metal is reduced.

Tollens test: Ag + (soluble)  Ag metal (mirror).


13 –27

Benedict’s solution, which is blue in color, turns brick red when an aldehyde reacts with it.

The aldehyde is oxidized and the metal is reduced.

Benedict’s test: Cu ++ (blue)  Cu + (brick red).


13 –28

Reduction of Aldehydes and Ketones

• Reduction is the reverse of the oxidation reaction. Reduction of a carbonyl group is the addition of hydrogens across the double bond to produce an –OH group.

• Aldehydes are reduced to primary alcohols, and ketones are reduced to secondary alcohols.

• Reduction of the carbonyl group occurs by formation of a bond to the carbonyl carbon by a hydride, H: , ion accompanied by bonding of a

H + ion to the carbonyl oxygen atom.


13 –29

Structural Characteristics and

Naming of Ketones


13 –30

Acetone, CH

3

(C=O)CH

3

): It is one of the most widely used solvents.

It can dissolve most organic compounds and is also miscible with water.

Acetone is highly volatile and is also highly flammable.

Ketones, like aldehydes, occur widely in Nature.

O

O

2-heptanone cloves


carvone spearmint flavoring

13 –31

• Some ketones are best known by their common names which give the names of the two alkyl groups bonded to the carbonyl group followed by the word ketone. For example, ethyl methyl ketone =

CH

3

-(C=O)-CH

2

-CH

3

• Ketones are named systematically (IUPAC) by replacing the final –e of the corresponding alkane name with –one. The numbering of the alkane chain begins at the end nearest to the carbonyl group.

The location of the carbonyl group is indicated by placing the number of the carbonyl carbon in front of the name; e.g. 2propanone = acetone. The above compound is

…

2-butanone


13 –32

Properties and Reactions of Ketones


13 –33

The physical properties of ketones closely parallel the properties of aldehydes; i.e. their boiling points are intermediate between alkanes and alcohols.

Ketones are not readily oxidized.

Ketones are readily reduced to secondary alcohols .

O

H

2

Ni catalyst


OH

13 –34

Chemistry at a Glance:

Reactions Involving Aldehydes and Ketones


13 –35

Carboxylic Acids


13 –36

Carboxylic Acids and Their Derivatives:

Properties and Names

• Caboxylic acids have an –OH group bonded to a carbonyl group.

In their derivatives, OH is substituted by other groups. Such as,

Esters have an –OR group bonded to a carbonyl group.

Amides have an –NH

2 group.

group bonded to a carbonyl


13 –37


are acidic

• Carboxylic acids donate a proton to bases.

• Carboxylic acids hydrogen bond with each other.

As a result of hydrogen bonding, they have higher boiling points than similar alkanes.


13 –38

Learn these names


13 –39

Two common NSAID’s (non-steroidal anti-inflammatory drugs) are Ibuprofen (a.k.a. Motrin and Advil) and

Naproxen (a.k.a. Naprosyn and Aleve). They are both carboxylic acids.

CO

2

H CO

2

H ibuprofen

O naproxen

Chronic long term used of these OTC drugs has recently been shown to increase the risk of heart disease.


13 –40

Advil and Aleve


13 –41

--Carboxylic acids have a sharp and strong odor.

--Up to four carbon containing carboxylic acids are water soluble.

--Carboxylic acids are named systematically (IUPAC) by replacing the –e at the end of the alkane name with – oic acid.

If alkyl or other substituents are present, the chain is numbered beginning at the

COOH end.


13 –42

O O

OH

Carboxylic acids have a higher priority when naming.

Therefore, this molecule is not named as a ketone, but instead is named as a carboxylic acid.

5-oxohexanoic acid

O

OH

2-ethyl-5-methylbenzoic acid


13 –43

 Dicarboxylic acids, which contain two

–COOH groups, include the biochemicals succinic acid, HOOC-CH

2

-CH

2

-COOH, and glutaric acid, HOOC-CH

2

-CH

2

-CH

2

-COOH.

 Unsaturated acids are named systematically in the IUPAC system with the ending –enoic acid.

 Acids with larger saturated alkyl groups are waxy, odorless solids.

 Water solubility decreases as the size of the alkyl group increases.


13 –44

Chemical Portraits:

Commonly Encountered Carboxylic Acids


13 –45

Properties and Reactions of



13 –46

Notes on Some Common Carboxylic Acids

• Formic acid, HCOOH: Chemical that is present in the sting of ants.

• Acetic acid, CH

3

COOH: dilute (5%) aqueous acetic acid is known as vinegar.

• Butyric acid, CH

3

CH

2

CH

2

COOH: Chemical responsible for odor of rancid butter.

• Amino acids, the building blocks of proteins, have the general formula R-CH(NH

2

)-COOH.

• Citric acid: Present in citrus fruits and blood.


13 –47

Acidity of Carboxylic Acids

• Carboxylic acids are weak acids.

• Acid strengths of common carboxylic acids are about the same as that for acetic acid.

• Carboxylic acids undergo neutralization reactions with bases and produce water and a carboxylic acid salt.

• The sodium and potassium salts of carboxylic acids are ionic solids that are more soluble in water than the carboxylic acids themselves.


13 –48

Carboxylic acids are acids because they donate a proton to a base; e.g. water.

O

OH

+ butyric acid

H

O

H

O

O

+

H

3

O

+ carboxylate ion hydronium ion

A carboxylate ion is a negative ion produced when a carboxylic acid loses a proton (acidic hydrogen atom).

In this case the equilibrium lies far to the left because carboxylic acids are weak acids and therefore do not completely ionize.


13 –49

Figure 13.7 A given carboxylic acid molecule can form two hydrogen bonds to another carboxylic acid molecule, producing a “dimer.” Dimers have twice the mass of a single molecule, and a higher temperature is needed to boil carboxylic acids than would be needed if no dimers were present.


13 –50

The boiling points of monocarboxylic acids compared to those of other types of compounds.

All compounds in the comparison have unbranched carbon chains.


13 –51

The solubility of saturated unbranched-chain carboxylic acids decreases as carbonchain length increases.


13 –52

Carboxylic acids react completely with strong bases such as NaOH. The resulting carboxylate salts are converted back to the carboxylic acid with strong acids.

O

OH

+ NaOH

O

O Na

+

+

H

2

O

+ NaCl

HCl

Carboxylic acids react with alcohols to produce esters.

O

OH

+ CH

3

OH

H

+ O

O

+ H

2

O


13 –53

Carboxylic acids react with amines to produce amides.

O

OH

+ NH

3 high temp

O

NH

2

+ H

2

O

Amides will be discussed in more detail in sections

13.10 and 13.11.


13 –54


Esters

13 –55

• The simple esters are colorless, volatile liquids with a pleasant smell.

• Esters are neither acids nor bases in aqueous solution.

• An ester’s name consists of two words. The name of the alkyl group in the ester group, -COOR, and the name of the parent carboxylic acid with the family name –oic replaced with –ate; e.g. ethyl acetate: CH

3(

C=O)OCH

2

CH

3 acetate ethyl


13 –56

Properties and Reactions of Esters


13 –57

Esters

To create an ester the

OH group of a carboxylic acid is replaced by an OR group. Esters cannot form hydrogen bonds with each other. Therefore, esters have lower boiling points than the carboxylic acids from which they are derived.


13 –58

FORMING ESTERS FROM CARBOXYLIC ACIDS

The reactions of alcohols (R-OH) and amines

(R-NH

2

) with carboxylic acids follow the same pattern – both replace the –OH group in the acid with another group.

Esterification: Esterification is carried out by warming a mixture of a carboxylic acid and an alcohol in the presence of a catalytic amount of a strong acid catalyst.

O

║

O

║

R-COH + H OR’ → R-C-OR’ + H

2

O acid alcohol ester water

This is an elimination reaction. Water is split out


13 –59

Aspirin and Other Over-the-Counter

Carboxylic Acid Derivatives

Aspirin: A member of a group of drugs known as salicylates.

Aspirin is an analgesic (relieves pain), antipyretic (reduces fever), and anti-inflammatory

(reduces inflammation).

Salicylates are esters of salicyclic acid.


13 –60

Esterification = forward reaction

COOH

+ CH

3

COOH

OH salicylic acid acetic acid

H

+ heat

COOH

O

O

CH

3 aspirin

Hydrolysis = reverse reaction = adding water to break a bond


13 –61

Selected Esters That Are Used as Flavoring Agents.


13 –62


Amides

13 –63

Amides

• Amides may contain an –NH with alkyl groups.

2 group or one or both of the hydrogens can be replaced

• Unsubstituted amides, RCONH

2

, can form three hydrogen bonds to other amide molecules and thus have higher melting and boiling points than the acids from which they are derived.


13 –64

• Monosubstituted amides, RCONHR’, can form hydrogen bonds to other amide molecules.

• Disubstituted amides, RCONR’

2

, can not form hydrogen bonds to other amide molecules, therefore, they have lower boiling points.


13 –65

• Unsubstituted amides, RCONH amide.

2

, are named by replacing the –oic acid by –

• Substituted amides are named by first specifying the alkyl group and then identifying the amide name. The alkyl substituents are preceded by the letter N to specify that the alkyl groups are attached to the nitrogen. Example:

CH

3

CONH-CH

2

CH

3

= N-ethylmethylamide


13 –66

Chemistry at a Glance:

Summary of Structural Relationships for Hydrocarbon

Derivatives: “H” versus “R”


13 –67

Urea is a one carbon amide. Its formation is the human body’s primary method of eliminating nitrogen “waste”.

The kidneys remove urea from the blood and provide a route for its excretion into the urine.

When the kidneys malfunction, urea concentration builds up to toxic levels, a condition known as uremia.

O

H

2

N NH

2

Note that urea is like formaldehyde with the –CH

3 replaced by –NH

2 groups groups


13 –68

Tylenol

Tylenol, a.k.a. acetaminophen, is an amide .

O

HN

OH

In this case the amine component is an aniline. The

IUPAC name is N-(4-hydroxyphenyl)-acetamide.


13 –69

Properties and Reactions of

Amides


13 –70

Amide Formation: Amides are formed by heating a mixture of a carboxylic acid and an amine.

The reaction is best accomplished by treating an acid chloride with ammonia or an amine.

O

Cl

+ NH

3

O

Cl

+ NH

2

R

O

Cl

+ HN R

R'


O

NH

2

+ HCl

O

N

H

R +

O

N

R'

R +

HCl

HCl

13 –71

Acetaminophen: An amide that also contains a hydroxyl group.

It is best known as Tylenol. It is an alternative to aspirin for pain relief, but unlike aspirin it is not an anti-inflammatory agent.


13 –72

Hydrolysis of Esters and Amides

Recall: Hydrolysis means the addition of water to split a bond.

Esters and amides undergo hydrolysis to give back the carboxylic acid and alcohol or amine.

Ester hydrolysis : Ester hydrolysis reactions can be catalyzed by either an acid or a base .

O

O

+ NaOH


O

ONa

+ CH

3

OH

13 –73

• Acid catalyzed ester hydrolysis is simply the reverse of esterification reaction. In this reaction, an ester is treated with water in the presence of a strong acid catalyst such as sulfuric acid.

• Base catalyzed ester hydrolysis with a base such as NaOH or KOH is known as saponification .

The product of anion rather then a free carboxylic acid.

a saponification reaction is a carboxylate


13 –74

Amide hydrolysis: Amides are stable in water, but undergo hydrolysis when heated in the presence of a base or an acid. The products of amide hydrolysis reactions in the presence of a base or an acid are shown below.


13 –75

Errors in the Text

Question 13.25(d) . The ring part of the structure shown should be a phenyl (benzene) group., i..e., a hexagon with a circle inside.

On page 353 : In the “Chemical Portrait” the structure shown is actually acetaldehyde, not acetone. (The text is correct for acetone.)

Acetone is CH

3

-(C=O)-CH

3

Bonuses: Students who are first to point out any error in the text in the chapters we cover will receive a bonus of 2 points.


13 –76

Condensation Polymers:

Polyesters and Polyamides


13 –77

CONDENSATION POLYMERS

These are formed by reacting difunctional monomers to give a polymer and a small molecule, usually water or

HCl. Note: condensation is the reverse of hydrolysis.

A polyester polymer is a condensation polymer in which the monomers are joined through ester linkages.

HO

O diacid

O

OH

+

HO

OH dialcohol

HO

O O

O

OH + H

2

O


O

O O

O

O

O

O

O

Poly(ethylene terephthalate), a polymer = PET

O

13 –78

Polyamides and Polyesters

• Polymer molecules are composed of thousands of repeating units, known as monomers.

• Both polyamides and polyesters are polymers; they have many uses.

• Polyamides are formed by reaction between diamines and diacids.

• Nylons are polyamides.

• Polyesters are formed by reaction between diacids and dialcohols.


13 –79

A polyamide is a condensation polymer in which the monomers are joined through amide linkages.

H

2

N

1,6-hexanediamine

NH

2

HN

H

N

O

+

O

HO hexanedioic acid

O

OH

O

N

H

Nylon 66

H

N

O

O


13 –80

A white strand of a nylon polymer forms between two layers of a solution containing a diacid

(bottom layer) and a diamine (top layer).


13 –81

POLYURETHANES

Polyurethanes are polymers related to polyesters and polyamides. The backbone of a polyurethane polymer contains aspects of both ester and amide functional groups.

O

O N

H

H

N O

O

O

O N

H

H

N O

O

O

O N

H

Foam rubber in furniture upholstery (e.g. on airplanes), packaging materials, life preservers, elastic fibers, and many other products such as skin substitute membranes

(Figure 13.13) contain polyurethane polymers.


13 –82

Chapter Summary

• Carbonyl compounds contain a carbonyl group

(C=O).

• Carbonyl groups are strongly polarized, with a partial positive charge on carbon and partial negative charge on oxygen.

• Carbonyl compounds are broadly divided into two groups: aldehydes and ketones are in one group and the second group contains carboxylic acids, esters, and amides.


13 –83

Chapter Summary (Cont’d

)

• Systematic or IUPAC names for aldehydes are derived by replacing –e at the end of the name of the alkane with –al.

• Ketones are named systematically by replacing the final –e of the corresponding alkane name with –one.

• Aldehydes and ketones do not form hydrogen bonds, as a result they have lower boiling points than alcohols of similar size.


13 –84

Chapter Summary (cont’d

)

• Aldehydes and ketones are soluble in common organic solvents, and those with fewer then five carbons are also soluble in water.

• Simple ketones are excellent solvents because they dissolve both polar and nonpolar compounds.

• Alcohols can be oxidized to aldehydes and ketones.

• Aldehydes can be further oxidized to carboxylic acids.

• Aldehydes are reduced to primary alcohols, and ketones are reduced to secondary alcohols.


13 –85

Chapter Summary (cont’d)

• Most carboxylic acids are weak acids but esters and amides are neither acids nor bases.

• Carboxylic acids, esters, and amides undergo carbonyl group substitution reactions.

• Simple acids and esters are liquids; all amides except formamide are solids.

• In esters, the -OH group in the acid is replaced by an -OR group of an alcohol.

• In amides, the -OH group in an acid is replaced by an –NH an NHR or –NR

2

2 group of ammonia, or group of a primary or secondary amine.


13 –86

In the News

The U.S. Environmental Protection Agency (EPA) has recently questioned the safety of perfluorooctanoic acid (PFOA), a compound employed in making teflon and a variety of nonstick

Items.

PFOA may be a carcinogen (a cancer-causing agent).

What is the formula of PFOA?

• “Perfluoro” means that all of the hydrogens attached to the carbons in the compound have been replaced by fluorine atoms.

• “Octanoic acid is an organic acid with 8 carbons, thus

PFOA = CF

3

-(CF

2

)

6

-COOH

Note that the acid hydrogen is not replaced by a fluorine.


13 –87

What you absolutely must know from Chapter 13

• You must know the general forms of the following compounds:

Aldehyde Ketone Carboxylic Acid Ester Amide

• How to name aldehydes, ketones, carboxylic acids, and esters.

• The common names of certain simple compounds: formaldehyde, acetone, formic acid, benzaldehyde, urea, formamide, acetamide,

• Some important reactions :

--Primary alcohols can be oxidized to form aldehydes.

--Secondary alcohols can be oxidized to form ketones.

--Aldehydes can be further oxidized to form carboxylic acids.

--Ketones resist oxidation

--Esters can be hydrolyzed to form an alcohol and a carboxylic acid

--Amides can be hydrolyzed to form an amine and a carboxylic acid

( Hydrolysis = adding water to split up a compound)


13 –88

Chapter 13 (continued)

• Polymers are large compound formed by linking smaller units called monomers.

• Condensation polymers are formed by reacting difunctional monomers and splitting out small molecules (e.g., H

2

O):

--A polyester is formed by the reaction of a diacid and a dialcohol:

HOOC-R-CO OH + H O-R’-OH  HOOC-R-CO-O-R’-OH + H

2 ester link

O

--A polyamide (such as nylon) can be formed from the reaction of a diacid and a diamine:

HOOC-R-CO OH + H HN-R’-NH  HOOC-R-CO-NH-R’-OH + H

2 amide link

O


13 –89

To Do List

• Read chapter 13!!

• Do additional problems

•

Do practice test T/F

•

Do practice test MC

• Review Lecture notes for

Chapter Thirteen


13 –90

Carboxylic Acids

Functional Groups Containing the

Carbon-Oxygen Double Bond

Structural Characteristics and

Naming of Aldehydes

Properties and Reactions of Aldehydes

Structural Characteristics and

Naming of Ketones

Properties and Reactions of Ketones