organic chemistry any molecule that contains the element carbon

ORGANIC CHEMISTRYORGANIC CHEMISTRYORGANIC CHEMISTRYORGANIC CHEMISTRYAny molecule that

contains the element CARBON

SUBSTITUTED HYDROCARBONS

Alkene A lkane

A lkyne R ing(Benzene)

HydrocarbonsONLY

Carbonand Hydrogen

Am ine Am ide

Substituded Hydrocarbons

+ N itrogen

organicacid

A lcohol

ester

ketone

aldehyde ether

Substituded Hydrocarbons

+ Oxygen

S u b s titu d ed

Hydrocarbons + Halogens

O rganicC hem istry

Substituted Hydro-

carbons

23.1 Introduction to Functional 23.1 Introduction to Functional GroupsGroups

5

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Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

A functional group is a specific arrangement of atoms in an organic compound that identify it as part of a

specific family.

Note that the double and triple bonds of alkenes and alkynes are considered the functional groups.

Organic compounds can be classified according to their functional groups.

Identify the Functional Group


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What is the general formula of a halocarbon?

• A halocarbon is an organic compound that contains at least one covalently

bonded fluorine, chlorine, bromine, or iodine atom.

HalocarbonsHalocarbons

ChloromethaneChloroethene


8

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What do mouthwash, perfume, and hairspray have in common?

They all contain an alcohol of some type.

An alcohol is an organic compound with an —OH group.

Alcohols Alcohols

Ethanol


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Interpret DataInterpret Data

Basic Chemistry Copyright © 2011 Pearson Education, Inc.10

Compounds with Oxygen Atoms

Alcohols• contain a hydroxyl

group (-OH)

Phenols

• contain a benzene ring

with a hydroxyl group.


Alcohols are named

• with an IUPAC name that replaces the e in alkane name with ol

CH4 methane

CH3─OH methanol

CH3─CH3 ethane

CH3─CH2─OH ethanol


Naming Alcohols


Name the following Alcohol

CH3 OH │ │CH3─CH─CH2─CH2─CH─CH3

STEP 1 Name the longest carbon chain with the OH group. A six-carbon chain attached to an OH is

hexanol


Naming an Alcohol (continued)

STEP 2 Number the chain starting at the end closer to the OH group.

CH3 OH │ │ CH3─CH─CH2─CH2─CH─CH36 5 4 3 2 1

STEP 3 Give the location and name of each substituent relative to the OH group.

5-methyl-2-hexanol


Name the following:

STEP 1 Name the longest carbon chain with the OH group. A four-carbon chain attached to an OH is

butanol.



2-methyl-1-butanol

CH3

│CH3─CH2─CH ─CH2─OH 4 3 2 1


Give the IUPAC name for the following:

OH CH3 | |CH3—CH—CH—CH2—CH3

STEP 1 Name the longest carbon chain with the OH group. A five-carbon chain attached to an OH is

pentanol.


1 2 3 4 5


3-methyl-2-pentanol

23.3 Carbonyl Compounds >23.3 Carbonyl Compounds >

17 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

The general formula of a carboxylic acid is RCOOH.

Carboxylic AcidsCarboxylic Acids



• The carboxylic acid CH3COOH is named ethanoic acid.


In the IUPAC system, carboxylic acids are named by replacing the -e ending of the parent structure with the ending -oic acid.




Some Saturated Aliphatic Carboxylic Acids

Molecular formula

Carbon atoms

IUPAC nameCommon

nameMelting

point (°C)

HCOOH 1 Methanoic acid Formic acid 8

CH3COOH 2 Ethanoic acid Acetic acid 17

CH3CH2COOH 3 Propanoic acid Propionic acid –22

CH3(CH2)2COOH 4 Butanoic acid Butyric acid –6

CH3(CH2)4COOH 6 Hexanoic acid Caproic acid –3

CH3(CH2)6COOH 8 Octanoic acid Caprylic acid 16

CH3(CH2)8COOH 10 Decanoic acid Capric acid 31

CH3(CH2)10COOH 12 Dodecanoic acid Lauric acid 44

CH3(CH2)12COOH 14 Tetradecanoic acid Myristic acid 58

CH3(CH2)14COOH 16 Hexadecanoic acid Palmitic acid 63

CH3(CH2)16COOH 18 Octadecanoic acid Stearic acid 70



Lemons and limes contain citric acid, a carboxylic acid that gives citrus fruits their sour flavor.



Carboxylic acids are named• in the IUPAC system by replacing the e in the alkane

name of the longest carbon chain with oic acid

H─COOH methanoic acid formic acid

CH3─COOH ethanoic acid acetic acid

CH3─CH2─COOH propanoic acid

CH3─CH2─CH2─COOH butanoic acid

Basic Chemistry Copyright © 2011 Pearson Education, Inc.

Naming Carboxylic Acids

22


Give the IUPAC name of the following Carboxylic Acid

CH3

| CH3—CH—CH2—COOH

STEP 1 Identify the carbon chain containing the carboxyl group and replace the e in the alkane name with oic acid.

butanoic acid


Example of Naming a Carboxylic Acid (continued)

STEP 2 Give the location and name of each substituent on the main chain by counting the carboxyl group as carbon 1.

CH3

| CH3—CH—CH2—COOH 4 3 2 1

3-methylbutanoic acid


Give the IUPAC name for the following: CH3 CH3

| | CH3─CH─CH2─CH─COOH

STEP 1 Identify the carbon chain containing the carboxyl group and replace the e with oic acid.

pentanoic acid

STEP 2 Give the location and name of each substituent on the main chain by counting the carboxyl group as carbon 1.

2,4-dimethylpentanoic acid

5 4 3 2 1



Aldehydes and Ketones

What structural characteristic do an aldehyde and a ketone share?

Aldehydes and KetonesAldehydes and Ketones

• A carbonyl group: it is a functional group with the general structure C O.



Some Common Aldehydes

IUPAC name (common name)

Structural formula Ball-and-stick model

Methanal(formaldehyde)

Ethanal(acetaldehyde)

Benzaldehyde(benzaldehyde)




Some Common Ketones

IUPAC name (common name)

Structural formula Ball-and-stick model

Propanone(acetone)

Diphenylmethanone(benzophenone)



29

Naming Naming AldehydesAldehydes

29


3030

Give the IUPAC name for the Give the IUPAC name for the following:following:

AldehydeAldehyde

Cl O │ ║

CH3─CH2─CH─CH2─C─H

STEP 1 Name the longest carbon chain containing the carbonyl group by replacing the e in the alkane name with al.

pentanal


3131

Aldehyde Aldehyde (continued)(continued)

STEP 2 Name and number substituents by counting the carbonyl group as carbon 1.

Cl O │ ║

CH3─CH2─CH─CH2─C─H 5 4 3 2 1

3-chloropentanal


3232

Draw the condensed structural Draw the condensed structural formula for 2,3-dichloropropanal.formula for 2,3-dichloropropanal.

STEP 1 Draw the main chain of carbon atoms. Propanal has three carbon atoms with an aldehyde

group. O ║

C─C─C─H 3 2 1

STEP 2 Number the chain and place the substituents on carbons indicated by the numbers.


3333

Solution (continued)Solution (continued)

Cl Cl O │ │ ║

C─C─C─H 3 2 1

STEP 3 Add the correct number of hydrogen atoms.

Cl Cl O │ │ ║

CH2─CH─C─H 2,3-dichloropropanal


3434

Naming KetonesNaming Ketones

In the name for a ketone, the• IUPAC name replaces the e in the alkane name

by one• common name identifies the alkyl groups attached to the carbonyl group in alphabetical

order and adds the word ketone


35

Naming KetonesNaming Ketones

35


3636

Give the IUPAC name for the following Ketone

O ║ Cl─CH2─CH2─C─CH2─Cl

STEP 1 Name the longest carbon chain containing the carbonyl group by replacing the e in the alkane name with one.

butanone


3737

Example of Example of Naming a Ketone Naming a Ketone (continued)(continued)

STEP 2 Number the carbon chain starting from the end nearer the carbonyl group and indicate its location.

O ║ Cl─CH2─CH2─C─CH2─Cl 4 3 2 1

STEP 3 Name and number any substituents on the carbon chain.

1,4-dichloro-2-butanone

2-butanone


3838

Give the IUPAC Give the IUPAC name for the name for the following:following:

CH3 O │ ║ CH3─CH2─CH─C─CH2─CH3

STEP 1 Name the longest carbon chain containing the carbonyl group by replacing the e in the alkane name with one.

hexanone


3939

SolutionSolution

STEP 2 Number the carbon chain starting from the end nearer the carbonyl group and indicate its location.

CH3 O │ ║ CH3─CH2─CH─C─CH2─CH3 6 5 4 3 2 1

3-hexanone

STEP 3 Name and number any substituents on the carbon chain.

CH3 O │ ║ CH3─CH2─CH─C─CH2─CH3 6 5 4 3 2 1

4-methyl-3-hexanone


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What is the general formula of an ether?

EthersEthers

• An ether is an organic compound in which oxygen is bonded to two carbon groups.


41

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Diethyl ether was the first reliable general anesthetic.

EthersEthers

• However, because diethyl ether is highly flammable and often

causes nausea, it was eventually replaced by

other anesthetics.


Ethers• contains an ─O─ between two carbon atoms

• has a common name of the two alkyl names followed by ether


Write the condensed structural formula of diethyl ether.

This ether contains an ─O─ attached to two ethyl groups (CH3─CH2─ ).

CH3─CH2─O─CH2─CH3



Esters are probably the most pleasant and delicious organic compounds one can study.

• Many esters have pleasant, fruity odors.

• Esters give blueberries, pineapples, apples, pears, bananas, and many other fruits their characteristic aromas.

• They also give many perfumes their fragrances.

EstersEsters



The general formula of an ester is RCOOR.

EstersEsters


Esterification

• is the reaction between a carboxylic acid and an alcohol

• uses an acid catalyst and heat O

║ H+, heatCH3 — C—OH + HO—CH2—CH3

O ║

CH3 — C—O—CH2—CH3 + H2O


Write the equation for the reaction of propanoic acid and methyl alcohol when heated in the presence of an acid catalyst.

O ║ H+, heatCH3—CH2—C—OH + HO—CH3

O ║CH3—CH2—C—O—CH3 + H2O


Esters

In an ester, the H in the carboxyl group is replaced with an alkyl group.

O ║

CH3—C—O—CH3

ester group

The ester methyl ethanoate (methyl acetate) is made from methyl alcohol and ethanoic acid (acetic acid).


The name of an ester includes

• name of the alkyl group from the alcohol • the name of the carbon chain from the acid

with the ic acid ending replaced by ate


Naming Esters

50


Example of Naming an Ester

Give the IUPAC and common names of the following compound, which is responsible for the flavor and odor of pears:

O ║

CH3—C—O—CH2—CH2—CH3

STEP 1 Write the name of the carbon chain from the alcohol as an

alkyl group. The alkyl group with three carbon atoms is propyl.


Example of Naming an Ester (continued)

STEP 2 Change the ic acid of the acid name to ate.In the IUPAC name, ethanoic acid is named ethanoate.

O

║ propylCH3—C—O—CH2—CH2—CH3

ethanoate

propyl ethanoate (IUPAC) propyl acetate (common)


O

║ CH3—CH2—CH2—C—O—CH2—CH3

Give the IUPAC for the following

STEP 1 Write the name of the carbon chain from the alcohol as an alkyl group.

STEP 2 Change the ic acid of the acid name to ate.

O

butanoate ║ ethyl CH3—CH2—CH2—C—O—CH2—CH3

ethyl butanoate (IUPAC)

ethyl


Draw the condensed structural formula of ethyl propionoate.

Opropionate ║ ethylCH3—CH2 —C—O—CH2—CH3


55

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What is the general formula of an amine?

AminesAmines

• An amine is an organic compound in which nitrogen is bonded to a carbon group.

Ethanamine


Amines

• are derivatives of ammonia, NH3

• contain N attached to one or more alkyl or aromatic groups


Naming Simple Amines

Simple amines have common names that list the alkyl groups attach to the N atom followed by amine.


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The -e ending of the parent hydrocarbon is changed to -amine.

– Ethanamine is used to make plastics, pharmaceuticals, and pesticides.

– Benzenamine is used to make furniture foam and some of the dyes that give clothes their colors.

AminesAmines

EthanamineBenzenamine


Learning Check

Give the common name for each of the following:

A. CH3—NH—CH2—CH3

CH3

|B. CH3—CH2—N—CH2—CH3

ethylmethylamine

diethylmethylamine


Draw the condensed structural formulas for

methylpropylamine

CH3–CH2–CH2–NH–CH3


61

>>Identify Identify FamilyFamily and and Functional Group

aldehyde Amine

AlkeneKetone

Acid

Alkane

ester

acid

acid

halogen

alcohol

alcohol

alcohol halogen

Chapter 17 – Organic Chemistry

4. The IUPAC name for isopropyl alcohol is:

A. 1–propanol

B. 2–phenol

C. 2–propanol

D. 1,2,3–propanetriolC. 2–propanol

Chapter 17 – Organic Chemistry

5. The correct name of CH3-O-CH2CH3 is:

A. diethyl ether

B. ethyl ether

C. methyl ethyl ether

D. ethyl methyl oxide

C. methyl ethyl ether


Concept Map

65

organic chemistry any molecule that contains the element carbon

Documents

oh group

oh ispentanol

functional groups

oh ch3 ch3chchch2ch3

ch3 oh ch3chch2ch2chch36

longest carbon chain

functional group23

organic compounds