Organic Chemistry Nomenclature Workbook

Organic Chemistry NomenclatureWorkbook

By:Rebekah ODonnell

Organic Chemistry NomenclatureWorkbook

By:Rebekah ODonnell

Online:< http://cnx.org/content/col29252/1.3/ >

This selection and arrangement of content as a collection is copyrighted by Rebekah ODonnell. It is licensed under

the Creative Commons Attribution License 4.0 (http://creativecommons.org/licenses/by/4.0/).

Collection structure revised: May 13, 2019

PDF generated: May 18, 2019

For copyright and attribution information for the modules contained in this collection, see p. 93.

Table of Contents

1 Unbranched Alkanes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 12 Constitutional Isomers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 33 Alkyl Substituents . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 74 Alkenes and Alkynes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 175 Halogens . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 276 Benzene and Conjugation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 337 Alcohols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 418 Ethers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 499 Aldehydes and Ketones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5310 Carboxylic acids and Esters . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 6711 Amines and Amides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 83Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 92Attributions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 93

iv

Available for free at Connexions <http://cnx.org/content/col29252/1.3>

Chapter 1

Unbranched Alkanes1

An alkane is a type of hydrocarbon (a compound consisting of only carbon and hydrogen atoms). Whenthe carbon-carbon backbone consists only of single bonds, the hydrocarbon contains as many hydrogen atomsas possible, and is therefore saturated. Alkanes are saturated hydrocarbons.

Unbranched alkanes have all their carbon atoms in a single chain.

Hexane

Figure 1.1: Hexane is an unbranched, saturated alkane containing six carbon atoms.

Below is a table of the names of unbranched, saturated alkanes containing up to ten carbons, with theircondensed structural formulas, molecular formulas, and boiling points.

1This content is available online at <http://cnx.org/content/m76439/1.4/>.


1

2 CHAPTER 1. UNBRANCHED ALKANES

Alkane Condensed Structural Formula Molecular Formula Boiling Point (degrees C)

Methane CH4 CH4 -161

Ethane CH3CH3 C2H6 -89

Propane CH3CH2CH3 C3H8 -42

Butane CH3CH2CH2CH3 -0.5

Pentane CH3(CH2)3CH3 36

Hexane CH3(CH2)4CH3 69

Heptane 98

Octane 126

Nonane 151

Decane 174

Table 1.1: Table of names, condensed structural formulas, molecular formulas, and boiling points ofunbranched saturated alkanes containing up to ten carbon atoms.

1) Fill in the blank spaces in the table.

2) Draw the structures of these ten unbranched alkanes, using Figure 1 (hexane) as a model.

3) What do the names of these molecules have in common?

4) What is the relationship between the number of carbon atoms and the number of hydrogen atoms in anunbranched alkane? Provide a general formula (use n for the number of carbon atoms).

5) Draw a graph of boiling points versus number of carbon atoms in unbranched alkanes.

6) How do the boiling points vary with the number of carbons? Propose an explanation for this observation.


Chapter 2

Constitutional Isomers1

Evaluate the two molecules below.

Two alkanes

Figure 2.1: Two alkanes for comparison

How are they the same?How are they di�erent?Two molecules which have the same molecular formula but di�erent structural formulas, or bonding

arrangements, are known as constitutional isomers.Pentane is an alkane with �ve carbon atoms. It has three constitutional isomers, shown below.



3

4 CHAPTER 2. CONSTITUTIONAL ISOMERS

Pentane

Figure 2.2: Unbranched isomer of pentane

Isopentane

Figure 2.3: Branched constitutional isomer of pentane


5

Neopentane

Figure 2.4: Branched constitutional isomer of pentane

Draw three constitutional isomers of heptane.Circle the constitutional isomers of hexane in the �gure below. Why are the remaining molecules not

considered to be constitutional isomers of hexane?

Figure 2.5

Draw the constitutional isomer of hexane that is missing.What is the minimum number of carbons in the chain of an alkane to be able to have a constitutional

isomer?


6 CHAPTER 2. CONSTITUTIONAL ISOMERS


Chapter 3

Alkyl Substituents1

An alkane can be appended onto an existing chain to create a branched molecule. This branched piece ofthe molecule is called a substituent. A substituent made from an alkane is called an alkyl group.

Alkyl groups are named similarly to unbranched alkane chains.

Alkane Condensed Structure Alkyl Group Condensed Structure

Methane CH4 Methyl CH3-

Ethane CH3CH3 Ethyl CH3CH2-

Propane CH3CH2CH3 Propyl CH3CH2CH2-

Butane CH3CH2CH2CH3 Butyl CH3CH2CH2CH2-

Table 3.1

Alkyl groups can also be branched. For example, there are three constitutional isomers of the butylsubstituent. In these diagrams, the negative charge on the carbon indicates the site of the bond from thesubstituent to the rest of the molecule.

isobutyl

Figure 3.1



7

8 CHAPTER 3. ALKYL SUBSTITUENTS

sec-butyl

Figure 3.2

tert-butyl

Figure 3.3

When naming molecules according to the IUPAC system of substitutive nomenclature, remember pre�x-parent-su�x (like un-believe-able).

pre�x: what are the substituents?parent: how many carbons in the parent chain?su�x: what is the family of compounds?In the case of an alkane, the su�x is -ane.The name of this molecule is 2-methylhexane. Identify the alkyl group. Label the parent chain carbons

from 1-6.


9

2-methylhexane

Figure 3.4

The name of this molecule is 3-methylheptane. Identify the alkyl group. Label the parent chain carbonsfrom 1-7.

3-methylheptane

Figure 3.5

Identify the alkyl group in Molecule A. Label the parent chain carbons from 1-8. What is the name ofthis molecule?



Molecule A

Figure 3.6

Identify the alkyl group in Molecule B. Label the parent chain carbons. What is the name of thismolecule?

Molecule B

Figure 3.7

The name of this molecule is 2,3-dimethylpentane.


11

2,3-dimethylpentane

Figure 3.8

What is the name of Molecule C?

Molecule C

Figure 3.9

The name of this molecule is 4-ethyl-2-methyloctane.



4-ethyl-2-methyloctane

Figure 3.10

What is the name of Molecule D?

Molecule D

Figure 3.11

The name of this molecule is 4-isopropylnonane.


13

4-isopropylnonane

Figure 3.12

What is the name of Molecule E?

Molecule E

Figure 3.13



The name of this molecule is cyclobutane.

cyclobutane

Figure 3.14

What is the name of Molecule F?

Molecule F

Figure 3.15

The name of this molecule is methylcyclobutane.


15

methylcyclobutane

Figure 3.16

The name of this molecule is 1-ethyl-2-methylcyclohexane.

1-ethyl-2-methylcyclohexane

Figure 3.17

What is the name of Molecule G?



Molecule G

Figure 3.18

Write the steps that you use to name an alkane, in order, as instructions for a student who doesn't knowhow to do it.

Draw any alkane and go through the steps in naming your molecule.


Chapter 4

Alkenes and Alkynes1

An alkane is a saturated hydrocarbon, meaning that the molecule contains all the possible hydrogen atomsbecause all the carbon-carbon bonds are single bonds. If one of those carbon-carbon bonds is a double bond,the resulting hydrocarbon is unsaturated and called an alkene.

This alkene is named propene.

propene

Figure 4.1

If one of the carbon-carbon bonds is a triple bond, the resulting hydrocarbon is called an alkyne.This alkyne is named ethyne.

ethyne

Figure 4.2



17

18 CHAPTER 4. ALKENES AND ALKYNES

What is the name of Molecule A?

Molecule A

Figure 4.3

The double or triple bond is called a functional group, and is often the site where chemical reactionsoccur. Like a substituent, it is speci�ed in the molecular name. When naming molecules according to theIUPAC system of nomenclature, remember pre�x-parent-su�x (like un-believe-able).

pre�x: what are the substituents?parent: how many carbons? If there is a double or triple carbon-carbon bond in the molecule, both

carbons in that bond must belong to the parent carbon chain, even if that chain does not have the greatestnumber of carbons.

su�x: what is the family of compounds?This molecule is named 2-pentene.

2-pentene

Figure 4.4

What is the name of Molecule B?


19

Molecule B

Figure 4.5


Molecule C

Figure 4.6

This molecule is named 4-methyl-2-pentene.

4-methyl-2-pentene

Figure 4.7




Molecule D

Figure 4.8

This molecule is named 3-isobutyl-1-octyne.

3-isobutyl-1-octyne

Figure 4.9



21

Molecule E

Figure 4.10

This molecule is named cyclohexene.

cyclohexene

Figure 4.11




Molecule F

Figure 4.12

This molecule is named 4-methylcyclohexene. Number the carbons.

4-methylcyclohexene

Figure 4.13



23

Molecule G

Figure 4.14

This molecule is named 1,3-pentadiene.

1,3-pentadiene

Figure 4.15

What is the name of Molecule H?



Molecule H

Figure 4.16

The location of substituents relative to the double bonds can lead to a type of constitutional isomerknown as a positional isomer.

The name of this molecule is 5-methyl-1,3-cyclohexadiene.

5-methyl-1,3-cyclohexadiene

Figure 4.17

What is the name of Molecule I?


25

Molecule I

Figure 4.18

Double or triple carbon-carbon bonds are rigid and planar. Since the carbons cannot rotate freely aroundthe bond, cis/trans isomers are common, and the orientation may be important for chemical reactions.

cis-2-butene and trans-2-butene

Figure 4.19

Write the steps that you use to name an alkene and an alkyne, in order, as instructions for a studentwho doesn't know how to do it.

Draw any alkene or alkyne and go through the steps in naming your molecule.


Chapter 5

Halogens1

The halogens are elements belonging to Group 7A. Fluorine, chlorine, bromine, and iodine canbe added to hydrocarbons through reactions with their diatomic forms or when bound to hydrogen ashydrogen halides.

Diatomic halogen vs halogen halide

Figure 5.1: where X is any halogen atom

When a halogen atom is bound to an otherwise saturated carbon atom, the molecule is known as analkyl halide.

Substituent Symbol Name

Fluorine Fl �uoro-

Chlorine Cl chloro-

Bromine Br bromo-

Iodine I iodo-

Table 5.1

When naming molecules according to the IUPAC system of nomenclature, remember pre�x-parent-su�x (like un-believe-able).

pre�x: what are the substituents?parent: how many carbons?su�x: what is the family of compounds?This molecule is named 2-chlorobutane.



27

28 CHAPTER 5. HALOGENS

2-chlorobutane

Figure 5.2


Molecule A

Figure 5.3

This molecule is named 2-�uoro-3-methylpentane.


29

2-�uoro-3-methylpentane

Figure 5.4

This molecule is named 4-iodo-2-methylhexane.

4-iodo-2-methylhexane

Figure 5.5




Molecule B

Figure 5.6

This molecule is named 1-chloro-2-butene.

1-chloro-2-butene

Figure 5.7

This molecule is named 5-�uoro-2-hexene.


31

5-�uoro-2-hexene

Figure 5.8


Molecule C

Figure 5.9

This molecule is named 5-�uoro-1,3-cyclohexadiene.



5-�uoro-1,3-cyclohexadiene

Figure 5.10


Molecule D

Figure 5.11

Write the steps that you use to name an alkyl halide, in order, as instructions for a student who doesn'tknow how to do it.

Draw any alkyl halide and go through the steps in naming your molecule.


Chapter 6

Benzene and Conjugation1

Aromatic hydrocarbons, like this benzene ring, have unexpected chemistry.

benzene

Figure 6.1

We would expect to name this molecule 1,3,5-cyclohexatriene and see its double bonds react like otherdouble bonds. However, these double bonds do not react in the same way as double bonds in a standardalkene. Observe the result of the below experiment under the appropriate reaction conditions.



33

34 CHAPTER 6. BENZENE AND CONJUGATION

Figure 6.2

This surprising stability of the double bonds in the benzene ring is not due to the cyclic arrangementof the carbon chain. Under the appropriate reaction conditions, we see the following results for addinghydrogen across the double bonds of the molecules below.


35

Figure 6.3

Measuring the bond lengths gives the following result.

Bond Type Bond Length (Angstroms)

Single 1.54

Double 1.34

Benzene 1.4

Table 6.1

Therefore, the three �double bonds� of the benzene ring are not true double bonds. The electrons areshared across all of the carbons in the ring, an arrangement called conjugation which is better representedby the below structure.



Figure 6.4

When depicting benzene rings using the double bond drawing, remember that the ring is a hybrid betweentwo equally likely resonance structures.

Figure 6.5

Therefore both structures below would be named 1-chlorobenzene.


37

1-chlorobenzene

Figure 6.6

When a benzene ring has two substituents, they are named based upon their position to each otherrather than by numbers.

o-dichlorobenzene

Figure 6.7: o is for ortho, with substituents at 1,2



m-chloromethylbenzene

Figure 6.8: m is for meta, with substituents at 1,3

p-chloro�uorobenzene

Figure 6.9: p is for para, with substituents at 1,4



39

Molecule A

Figure 6.10

A benzene ring can be a substituent.The name of this molecule is 2-phenyldecane.

2-phenyldecane

Figure 6.11




Molecule B

Figure 6.12

Conjugation is not limited to cyclic structures. One of the two molecules below does not react withhalogen halides under standard reaction conditions. Which molecule do you predict is the more stable one?Why? What prediction would you make about the lengths of its carbon-carbon bonds?

Figure 6.13

Write the steps that you use to name a benzene derivative or a molecule containing a benzene ring as asubstituent, in order, as instructions for a student who doesn't know how to do it.

Draw any benzene-containing molecule and go through the steps in naming your molecule.


Chapter 7

Alcohols1

In organic chemistry, any alkyl group can be abbreviated as R. An alcohol, in which a hydroxy (-OH)group is attached to a carbon of the alkyl group, can be abbreviated as R-OH.

The name of this molecule is ethanol.

ethanol

Figure 7.1


Molecule A

Figure 7.2

This molecule is named 2-butanol.



41

42 CHAPTER 7. ALCOHOLS

2-butanol

Figure 7.3

This molecule is named 6-isopropyl-5-nonanol. Number the carbons.

6-isopropyl-5-nonanol

Figure 7.4

Number the carbons. What is the name of Molecule B?


43

Molecule B

Figure 7.5

The name of this molecule is 3-propyl-2-octanol. Number the carbons.

3-propyl-2-octanol

Figure 7.6

Number the carbons. What is the name of molecule C?



Molecule C

Figure 7.7

This molecule is named 3-�uorocyclohexanol. Number the carbons.

3-�uorocyclohexanol

Figure 7.8

Number the carbons. What is the name of Molecule D?


45

Molecule D

Figure 7.9

This molecule is named 4-hexen-2-ol. Number the carbons.

4-hexen-2-ol

Figure 7.10

Number the carbons. What is the name of Molecule E?



Molecule E

Figure 7.11

This molecule is named 2,3-pentanediol.

2,3-pentanediol

Figure 7.12



47

Molecule F

Figure 7.13

If a hydroxy (-OH) group is attached to an aromatic ring system, it is called a phenol.

Two phenols

Figure 7.14

This molecule is named 2-chlorophenol or o-chlorophenol.



2-chlorophenol / o-chlorophenol

Figure 7.15

Name Molecule G using 1) numbers and 2) the o/m/p nomenclature.

Molecule G

Figure 7.16

What additions do we make to our existing naming rules to name alcohols?Write the steps that you use to name an alcohol in order, as instructions for a student who doesn't know

how to do it.Draw any alcohol and go through the steps in naming your molecule.


Chapter 8

Ethers1

In organic chemistry, any alkyl group can be abbreviated as R. An ether, in which the carbons of twoalkyl groups are linked to the same oxygen, can be abbreviated as R-O-R.

This molecule is often referred to simply as �ether�. Its common name is diethyl ether, and its IUPACname is ethoxyethane.

ethoxyethane

Figure 8.1

The common name of this molecule is ethyl methyl ether, and its IUPAC name is methoxyethane.

methoxyethane

Figure 8.2



49

50 CHAPTER 8. ETHERS

What are the common and IUPAC names of Molecule A?

Molecule A

Figure 8.3

The name of this molecule is 2-methoxy-3-methylbutane. Number the carbons.

2-methoxy-3-methylbutane

Figure 8.4



51

Molecule B

Figure 8.5

The name of this molecule is 4-butoxy-2-butanol. Number the carbons.

4-butoxy-2-butanol

Figure 8.6

Number the carbons. What is the name of Molecule C?


52 CHAPTER 8. ETHERS

Molecule C

Figure 8.7

What additions do we make to our existing naming rules to name ethers?Write the steps that you use to name an ether in order, as instructions for a student who doesn't know

how to do it.Draw any ether and go through the steps in naming your molecule.


Chapter 9

Aldehydes and Ketones1

A carbonyl group consists of a carbon atom double-bonded to an oxygen atom, written as C=O. Alde-hydes and ketones are two compounds which contain the carbonyl group.

aldehyde

Figure 9.1: The R group can also be a hydrogen.



53

54 CHAPTER 9. ALDEHYDES AND KETONES

ketone

Figure 9.2: The R groups can be the same or di�erent.

Aldehydes and ketones are constitutional isomers. For example, the aldehyde and ketone belowboth have the molecular formula C3H6O.

C3H6O

Figure 9.3

The simplest aldehyde is methanal, commonly known as formaldehyde, and used as a preservative.


55

methanal

Figure 9.4

The name of this molecule is butanal.

butanal

Figure 9.5




Molecule A

Figure 9.6

This molecule is named 5-methylhexanal. Number the carbons.

5-methylhexanal

Figure 9.7



57

Molecule B

Figure 9.8

This molecule is named 3-ethyl-4-methylhexanal. Number the carbons.

3-ethyl-4-methylhexanal

Figure 9.9

Number the carbons. What is the name of Molecule C?



Molecule C

Figure 9.10

This molecule is named 3-pentenal. Number the carbons.

3-pentenal

Figure 9.11

Number the carbons. What is the name of Molecule D?


59

Molecule D

Figure 9.12

A well-known ketone is 2-propanone, commonly known as acetone, and used as a nail polish remover.

2-propanone

Figure 9.13

This molecule is named 2-pentanone.



2-pentanone

Figure 9.14


Molecule E

Figure 9.15

The name of this molecule is 5-ethyl-2-heptanone. Number the carbons.


61

5-ethyl-2-heptanone

Figure 9.16

Number the carbons. What is the name of Molecule F?

Molecule F

Figure 9.17

This molecule is named 6-chloro-4-ethyl-3-heptanone. Number the carbons.



6-chloro-4-ethyl-3-heptanone

Figure 9.18

Number the carbons. What is the name of Molecule G?

Molecule G

Figure 9.19

The name of this molecule is 3-bromocyclohexanone. Number the carbons.


63

3-bromocyclohexanone

Figure 9.20

Number the carbons. What is the name of Molecule H?

Molecule H

Figure 9.21

The name of this molecule is 4-hydroxy-2-butanone. Number the carbons.



4-hydroxy-2-butanone

Figure 9.22

Number the carbons. What is the name of Molecule I?

Molecule I

Figure 9.23

This molecule is named 5-chloro-4-oxohexanal. Number the carbons.


65

5-chloro-4-oxohexanal

Figure 9.24

Number the carbons. What is the name of Molecule J?

Molecule J

Figure 9.25

What additions do we make to our existing naming rules to name aldehydes and ketones?Write the steps that you use to name an aldehyde or ketone in order, as instructions for a student who

doesn't know how to do it.Draw any aldehyde or ketone and go through the steps in naming your molecule.


Chapter 10

Carboxylic acids and Esters1

A carbonyl group consists of a carbon atom double-bonded to an oxygen atom, written as C=O. When ahydroxy (-OH) group is also bound to the carbonyl carbon, the resulting group is known as a carboxygroup. Carboxylic acids contain the carboxy group, and one type of carboxylic acid derivative is anester.

carboxylic acid

Figure 10.1



67

68 CHAPTER 10. CARBOXYLIC ACIDS AND ESTERS

ester

Figure 10.2

Carboxylic acids are often abbreviated as R-COOH or R-CO2H. Some simple carboxylic acids, suchas acetic acid and benzoic acid, are referred to primarily by their common names.

acetic acid and benzoic acid

Figure 10.3

The common name of this molecule is valeric acid. Its formal name is pentanoic acid.


69

pentanoic acid

Figure 10.4

The common name of Molecule A is caprylic acid. What is the formal name of Molecule A?

Molecule A

Figure 10.5

The name of this molecule is hexanedioic acid.



hexanedioic acid

Figure 10.6


Molecule B

Figure 10.7

The name of this molecule is cyclohexanecarboxylic acid.


71

cyclohexanecarboxylic acid

Figure 10.8


Molecule C

Figure 10.9

The name of this molecule is 1,2-benzenedicarboxylic acid.



1,2-benzenedicarboxylic acid

Figure 10.10


Molecule D

Figure 10.11


73

The name of this molecule is 4-bromopentanoic acid. Number the carbons.

4-bromopentanoic acid

Figure 10.12

Number the carbons. What is the name of Molecule E?

Molecule E

Figure 10.13

This molecule is named 2-hydroxybutanoic acid (also known as lactic acid).



2-hydroxybutanoic acid

Figure 10.14


Molecule F

Figure 10.15

This molecule is named 3,6-dioxo-4-hydroxyhexanoic acid.


75

3,6-dioxo-4-hydroxyhexanoic acid

Figure 10.16


Molecule G

Figure 10.17

Esters are often manufactured to provide fragrance. One example is isobutyl methanoate, which smellslike raspberries.



isobutyl methanoate

Figure 10.18

The process of esteri�cation involves adding an alcohol to a carboxylic acid in the presence of hydrogenions.

esteri�cation

Figure 10.19

To name an ester, �rst we name the alcohol used, and then the carboxylic acid. Below is shown theesteri�cation reaction of ethanol and propanoic acid to create ethyl propanoate.


77

synthesis of ethyl propanoate

Figure 10.20

What is the name of Molecule H?

Molecule H

Figure 10.21

What is the name of Molecule I?



Molecule I

Figure 10.22

This molecule is named dimethylbutanedioate.

dimethylbutanedioate

Figure 10.23

What is the name of Molecule J?


79

Molecule J

Figure 10.24

This molecule is named 2-chloroethyl propanoate.

2-chloroethyl propanoate

Figure 10.25

What is the name of Molecule K?



Molecule K

Figure 10.26

This molecule is named 2-bromopropyl 4-chlorobutanoate. Number the carbons.

2-bromopropyl 4-chlorobutanoate

Figure 10.27

Number the carbons. What is the name of Molecule L?


81

Molecule L

Figure 10.28

What additions do we make to our existing naming rules to name carboxylic acids and esters?Write the steps that you use to name a carboxylic acid in order, as instructions for a student who doesn't

know how to do it.Draw any carboxylic acid and go through the steps in naming your molecule.Write the steps that you use to name an ester in order, as instructions for a student who doesn't know

how to do it.Draw any ester and go through the steps in naming your molecule.


Chapter 11

Amines and Amides1

An amino group consists of a nitrogen atom bonded to two hydrogen atoms, written as -NH2. If thehydrogens are replaced by R groups, the group is referred to as a substituted amino group. Aminesand amides are two compounds which contain amino or substituted amino groups.

Amines are designated as primary, secondary, or tertiary amines based upon the degree of sub-stitution of the amino group. For example, an amine in which all three of the potential nitrogen bonds arewith R groups instead of hydrogens is called a tertiary amine (see the right-most molecule below).

primary, secondary, and tertiary amines

Figure 11.1

Despite the complexity of the below molecule, because the nitrogen is directly bound to two hydrogensand only one R group, it is a primary amine.



83

84 CHAPTER 11. AMINES AND AMIDES

an enormous primary amine

Figure 11.2

There are multiple substitutive nomenclatures for naming amines, with the two most common beingIUPAC and Chemical Abstract Service. Both will be described below.

This molecule is named 2-pentanamine (CAS) or 2-aminopentane (IUPAC).

2-pentanamine (CAS) / 2-aminopentane (IUPAC)

Figure 11.3

What are the names of Molecule A?


85

Molecule A

Figure 11.4

This molecule is named 1,6-hexanediamine (CAS) or 1,6-diaminohexane (IUPAC).

1,6-hexanediamine (CAS) / 1,6-diaminohexane (IUPAC)

Figure 11.5

What are the names of Molecule B?

Molecule B

Figure 11.6



This molecule is named N,N-dimethylethanamine (CAS) or dimethylaminoethane (IUPAC).

N,N-dimethylethanamine (CAS) / dimethylaminoethane (IUPAC)

Figure 11.7

What are the names of Molecule C?

Molecule C

Figure 11.8

This molecule is named 4-amino-2-pentanone (CAS) or 4-aminopentan-2-one (IUPAC). Number the car-bons.


87

4-amino-2-pentanone (CAS) / 4-aminopentane-2-one (IUPAC)

Figure 11.9

Number the carbons. What are the names of Molecule D?

Molecule D

Figure 11.10

This molecule is named 2-(N-methylamino)ethanol (CAS) or 2-methylaminoethanol (IUPAC). Numberthe carbons.



2-(N-methylamino)ethanol (CAS) / 2-methylaminoethanol (IUPAC)

Figure 11.11

Number the carbons. What are the names of Molecule E?

Molecule E

Figure 11.12

An amide is a carboxylic acid derivative in which the carboxyl -OH has been replaced withan amino or substituted amino group. Amides are also described as primary, secondary, or tertiarydepending on the number of R groups bound directly to the nitrogen.


89

primary, secondary, and tertiary amides

Figure 11.13

The naming of simple amides is based on the carboxylic acid nomenclature, and keeps the same name inthe CAS and IUPAC systems.

The name of this molecule is 3-methylbutanamide.

3-methylbutanamide

Figure 11.14




Molecule F

Figure 11.15

The name of this molecule is N-methylbenzamide.

N-methylbenzamide

Figure 11.16



91

Molecule G

Figure 11.17

What additions do we make to our existing naming rules to name amines and amides, in the substitutivenaming system that you use?

Write the steps that you use to name an amine in order, as instructions for a student who doesn't knowhow to do it.

Draw any amine and go through the steps in naming your molecule.Write the steps that you use to name an amide in order, as instructions for a student who doesn't know

how to do it.Draw any amide and go through the steps in naming your molecule.


92 INDEX

Index of Keywords and Terms

Keywords are listed by the section with that keyword (page numbers are in parentheses). Keywordsdo not necessarily appear in the text of the page. They are merely associated with that section. Ex.apples, � 1.1 (1) Terms are referenced by the page they appear on. Ex. apples, 1

A acid, � 10(67)alcohol, � 7(41)aldehyde, � 9(53)alkane, � 1(1), � 2(3)alkene, � 4(17)alkyl, � 3(7)alkyne, � 4(17)amide, � 11(83)amine, � 11(83)aromatic, � 6(33)

B benzene, � 6(33)bond, � 4(17)

C carbonyl, � 9(53)carboxylic, � 10(67)chemistry, � 1(1), � 3(7), � 4(17), � 5(27),� 6(33), � 7(41), � 8(49), � 9(53), � 10(67),� 11(83)conjugation, � 6(33)constitutional, � 2(3)

D double, � 4(17)

E ester, � 10(67)ether, � 8(49)

G group, � 3(7)

H halide, � 5(27)halogen, � 5(27)halogenated, � 5(27)hydrocarbon, � 1(1)

I isomer, � 2(3)

K ketone, � 9(53)

N naming, � 1(1), � 3(7), � 4(17), � 5(27), � 6(33),� 7(41), � 8(49), � 9(53), � 10(67), � 11(83)nomenclature, � 1(1), � 3(7), � 4(17), � 5(27),� 6(33), � 7(41), � 8(49), � 9(53), � 10(67),� 11(83)

O organic, � 1(1), � 3(7), � 4(17), � 5(27), � 6(33),� 7(41), � 8(49), � 9(53), � 10(67), � 11(83)

S saturated, � 1(1)substituent, � 3(7)

T triple, � 4(17)

U unbranched, � 1(1)


ATTRIBUTIONS 93

Attributions

Collection: Organic Chemistry Nomenclature Workbook

Edited by: Rebekah ODonnellURL: http://cnx.org/content/col29252/1.3/License: http://creativecommons.org/licenses/by/4.0/

Module: "Unbranched Alkanes"By: Rebekah ODonnellURL: http://cnx.org/content/m76439/1.4/Pages: 1-2Copyright: Rebekah ODonnellLicense: http://creativecommons.org/licenses/by/4.0/

Module: "Constitutional Isomers (Alkanes)"Used here as: "Constitutional Isomers"By: Rebekah ODonnellURL: http://cnx.org/content/m76440/1.1/Pages: 3-5Copyright: Rebekah ODonnellLicense: http://creativecommons.org/licenses/by/4.0/

Module: "Naming Alkyl Substituents"Used here as: "Alkyl Substituents"By: Rebekah ODonnellURL: http://cnx.org/content/m76443/1.3/Pages: 7-16Copyright: Rebekah ODonnellLicense: http://creativecommons.org/licenses/by/4.0/

Module: "4. Alkenes and Alkynes"Used here as: "Alkenes and Alkynes"By: Rebekah ODonnellURL: http://cnx.org/content/m76445/1.4/Pages: 17-25Copyright: Rebekah ODonnellLicense: http://creativecommons.org/licenses/by/4.0/

Module: "5. Halogens"Used here as: "Halogens"By: Rebekah ODonnellURL: http://cnx.org/content/m76446/1.3/Pages: 27-32Copyright: Rebekah ODonnellLicense: http://creativecommons.org/licenses/by/4.0/

Module: "6. Benzene and Conjugation"Used here as: "Benzene and Conjugation"By: Rebekah ODonnellURL: http://cnx.org/content/m76447/1.2/Pages: 33-40Copyright: Rebekah ODonnellLicense: http://creativecommons.org/licenses/by/4.0/


94 ATTRIBUTIONS

Module: "7. Alcohols"Used here as: "Alcohols"By: Rebekah ODonnellURL: http://cnx.org/content/m76448/1.2/Pages: 41-48Copyright: Rebekah ODonnellLicense: http://creativecommons.org/licenses/by/4.0/

Module: "8. Ethers"Used here as: "Ethers"By: Rebekah ODonnellURL: http://cnx.org/content/m76568/1.2/Pages: 49-52Copyright: Rebekah ODonnellLicense: http://creativecommons.org/licenses/by/4.0/

Module: "9. Aldehydes and Ketones"Used here as: "Aldehydes and Ketones"By: Rebekah ODonnellURL: http://cnx.org/content/m76583/1.2/Pages: 53-65Copyright: Rebekah ODonnellLicense: http://creativecommons.org/licenses/by/4.0/

Module: "10. Carboxylic acids and Esters"Used here as: "Carboxylic acids and Esters"By: Rebekah ODonnellURL: http://cnx.org/content/m76665/1.2/Pages: 67-81Copyright: Rebekah ODonnellLicense: http://creativecommons.org/licenses/by/4.0/

Module: "11. Amines and amides"Used here as: "Amines and Amides"By: Rebekah ODonnellURL: http://cnx.org/content/m76666/1.2/Pages: 83-91Copyright: Rebekah ODonnellLicense: http://creativecommons.org/licenses/by/4.0/


Organic Chemistry Nomenclature WorkbookThis workbook guides the student through learning how to name organic chemistry molecules. Through theuse of examples, the learner determines the correct nomenclature for each type of molecule. Rules derivedby the student through active engagement are easier to remember than rote memorization.

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