ORGANIC CHEMISTRY

NOMENCLATURE
WORKBOOK

Rebekah O'Donnell
Boston University
Book: Organic Chemistry Nomenclature
Workbook (O'Donnell)
This text is disseminated via the Open Education Resource (OER) LibreTexts Project
([Link] and like the thousands of other texts available within this powerful platform, it is
freely available for reading, printing, and "consuming."
The LibreTexts mission is to bring together students, faculty, and scholars in a collaborative effort to
provide and accessible, and comprehensive platform that empowers our community to develop, curate,
adapt, and adopt openly licensed resources and technologies; through these efforts we can reduce the
financial burden born from traditional educational resource costs, ensuring education is more accessible
for students and communities worldwide.
Most, but not all, pages in the library have licenses that may allow individuals to make changes, save,
and print this book. Carefully consult the applicable license(s) before pursuing such effects. Instructors
can adopt existing LibreTexts texts or Remix them to quickly build course-specific resources to meet the
needs of their students. Unlike traditional textbooks, LibreTexts’ web based origins allow powerful
integration of advanced features and new technologies to support learning.

LibreTexts is the adaptable, user-friendly non-profit open education resource platform that educators
trust for creating, customizing, and sharing accessible, interactive textbooks, adaptive homework, and
ancillary materials. We collaborate with individuals and organizations to champion open education
initiatives, support institutional publishing programs, drive curriculum development projects, and more.
The LibreTexts libraries are Powered by NICE CXone Expert and was supported by the Department of
Education Open Textbook Pilot Project, the California Education Learning Lab, the UC Davis Office of
the Provost, the UC Davis Library, the California State University Affordable Learning Solutions
Program, and Merlot. This material is based upon work supported by the National Science Foundation
under Grant No. 1246120, 1525057, and 1413739.
Any opinions, findings, and conclusions or recommendations expressed in this material are those of the
author(s) and do not necessarily reflect the views of the National Science Foundation nor the US
Department of Education.
Have questions or comments? For information about adoptions or adaptions contact
info@[Link] or visit our main website at [Link]
This text was compiled on 09/10/2025
TABLE OF CONTENTS
Licensing

1: Chapters
1.1: Unbranched Alkanes
1.2: Constitutional Isomers
1.3: Alkyl Substituents
1.4: Alkenes and Alkynes
1.5: Halogens
1.6: Benzene and Conjugation
1.7: Alcohols
1.8: Ethers
1.9: Aldehydes and Ketones
1.10: Carboxylic acids and Esters
1.11: Amines and Amides

Index

Glossary
Detailed Licensing

1 [Link]
Licensing
A detailed breakdown of this resource's licensing can be found in Back Matter/Detailed Licensing.

1 [Link]
 CHAPTER OVERVIEW

1: Chapters
1.1: Unbranched Alkanes
1.2: Constitutional Isomers
1.3: Alkyl Substituents
1.4: Alkenes and Alkynes
1.5: Halogens
1.6: Benzene and Conjugation
1.7: Alcohols
1.8: Ethers
1.9: Aldehydes and Ketones
1.10: Carboxylic acids and Esters
1.11: Amines and Amides

1: Chapters is shared under a not declared license and was authored, remixed, and/or curated by LibreTexts.

1
1.1: Unbranched Alkanes
 Learning Objective
Naming Unbranched Alkanes (Organic Chemistry)

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

Figure 1.1.1 . Hexane is an unbranched, saturated alkane containing six carbon atoms: Hexane
Below is a table of the names of unbranched, saturated alkanes containing up to ten carbons, with their condensed structural
formulas, molecular formulas, and boiling points.

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 of names, condensed structural formulas, molecular formulas, and boiling points of unbranched saturated alkanes containing
up to ten carbon atoms.

 Practice Questions
1. Fill in the blank spaces in the table.
2. Draw the structures of these ten unbranched alkanes, using Figure 1.1.1 (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 an unbranched 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.

This page titled 1.1: Unbranched Alkanes is shared under a CC BY 4.0 license and was authored, remixed, and/or curated by Rebekah O'Donnell
(OpenStax CNX) .

1.1.1 [Link]
1.2: Constitutional Isomers
 Learning Objective
Introduction to constitutional isomers using alkanes

Evaluate the two molecules below (Figure 1.2.1).

Figure 1.2.1 . Two alkanes for comparison

How are they the same?
How are they different?
Two molecules which have the same molecular formula but different structural formulas, or bonding arrangements, are known as
constitutional isomers.
Pentane is an alkane with five carbon atoms. It has three constitutional isomers, shown below.

Figure 1.2.2 . Unbranched isomer of Figure 1.2.3. Branched constitutional Figure 1.2.4. Branched constitutional
pentane isomer of pentane isomer of pentane

 Practice Questions

1. Draw three constitutional isomers of heptane.

2. Circle the constitutional isomers of hexane in the figure below. Why are the remaining molecules not considered to be
constitutional isomers of hexane?

Figure 1.2.5
3. Draw the constitutional isomer of hexane that is missing.
4. What is the minimum number of carbons in the chain of an alkane to be able to have a constitutional isomer?

This page titled 1.2: Constitutional Isomers is shared under a CC BY 4.0 license and was authored, remixed, and/or curated by Rebekah
O'Donnell (OpenStax CNX) .

1.2.1 [Link]
1.3: Alkyl Substituents
 Learning Objective
How to name organic molecules with alkyl substituents

An alkane can be appended onto an existing chain to create a branched molecule. This branched piece of the 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-

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

CH2- CH-
C-
Figure 1.3.1. Isobutyl Figure 1.3.2. Sec-butyl Figure 1.3.3. Tert-butyl

When naming molecules according to the IUPAC system of substitutive nomenclature, remember prefix-parent-suffix (like un-
believe-able).
1. prefix: what are the substituents?
2. parent: how many carbons in the parent chain?
3. suffix: what is the family of compounds?
In the case of an alkane, the suffix is -ane.

 Practice Questions

1. The name of this molecule is 2-methylhexane. Identify the alkyl group. Label the parent chain carbons from 1-6.

Figure 1.3.4 : 2-methylhexane

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

Figure 1.3.5 : 3-methylheptane

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

Figure 1.3.6 : Molecule A

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

Figure 1.3.7 : Molecule B

1.3.1 [Link]
5. The name of this molecule is 2,3-dimethylpentane.

Figure 1.3.8 : 2,3-dimethylpentane

What is the name of Molecule C?

Figure 1.3.9 : Molecule C

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

Figure 1.3.10 : 4-ethyl-2-methyloctane

What is the name of Molecule D?

Figure 1.3.11 : Molecule D

7. The name of this molecule is 4-isopropylnonane.

Figure 1.3.12 : 4-isopropylnonane

What is the name of Molecule E?

Figure 1.3.13 : Molecule E

8. The name of this molecule is cyclobutane.

Figure 1.3.14 : cyclobutane

What is the name of Molecule F?

Figure 1.3.15 : Molecule F

9. The name of this molecule is methylcyclobutane.

Figure 1.3.16 : methylcyclobutane

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

1.3.2 [Link]
 Figure 1.3.17 : 1-ethyl-2-methylcyclohexane
What is the name of Molecule G?

Figure 1.3.18 : Molecule G

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

This page titled 1.3: Alkyl Substituents is shared under a CC BY 4.0 license and was authored, remixed, and/or curated by Rebekah O'Donnell
(OpenStax CNX) .

1.3.3 [Link]
1.4: Alkenes and Alkynes
 Learning Objective
How to name alkenes and alkynes.

An alkane is a saturated hydrocarbon, meaning that the molecule contains all the possible hydrogen atoms because 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.

Figure 1.4.1 : propene

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

 Practice Question

1. This alkyne is named ethyne.

HC CH

Figure 1.4.2 : ethyne

What is the name of Molecule A?
H 3C CH

Figure 1.4.3 : Molecule A

The double or triple bond is called a functional group, and is often the site where chemical reactions occur. Like a substituent, it is
specified in the molecular name. When naming molecules according to the IUPAC system of nomenclature, remember prefix-
parent-suffix (like un-believe-able).
prefix: 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 greatest number of carbons.
suffix: what is the family of compounds?

 Practice Questions

1. This molecule is named 2-pentene.

Figure 1.4.4 : 2-pentene

What is the name of Molecule B?

Figure 1.4.5 : Molecule B

What is the name of Molecule C?

Figure 1.4.6 : Molecule C

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

Figure 1.4.7 : 4-methyl-2-pentene

What is the name of Molecule D?

Figure 1.4.8 : Molecule D

1.4.1 [Link]
 3. This molecule is named 3-isobutyl-1-octyne.

Figure 1.4.9 : 3-isobutyl-1-octyne

What is the name of Molecule E?

Figure 1.4.10 : Molecule E

4. This molecule is named cyclohexene.

Figure 1.4.11 : cyclohexene

What is the name of Molecule F?

Figure 1.4.12 : Molecule F

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

Figure 1.4.13 : 4-methylcyclohexene

What is the name of Molecule G?

Figure 1.4.14 : Molecule G

6. This molecule is named 1,3-pentadiene.

Figure 1.4.15 : 1,3-pentadiene

What is the name of Molecule H?

Figure 1.4.16 : Molecule H

7. The location of substituents relative to the double bonds can lead to a type of constitutional isomer known as a positional
isomer.
The name of this molecule is 5-methyl-1,3-cyclohexadiene.

Figure 1.4.17 : 5-methyl-1,3-cyclohexadiene

What is the name of Molecule I?

Figure 1.4.18 : Molecule I

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

Figure 1.4.19 : cis-2-butene and trans-2-butene

1.4.2 [Link]
  Practice Questions
1. Write the steps that you use to name an alkene and an alkyne, in order, as instructions for a student who doesn't know how
to do it.
2. Draw any alkene or alkyne and go through the steps in naming your molecule.

This page titled 1.4: Alkenes and Alkynes is shared under a CC BY 4.0 license and was authored, remixed, and/or curated by Rebekah O'Donnell
(OpenStax CNX) .

1.4.3 [Link]
1.5: Halogens
 Learning Objective
How to name halogenated hydrocarbons

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

Figure 1.5.1 . where X is any halogen atom:Diatomic halogen vs halogen halide

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

Substituent Symbol Name

Fluorine Fl fluoro-

Chlorine Cl chloro-

Bromine Br bromo-

Iodine I iodo-

When naming molecules according to the IUPAC system of nomenclature, remember prefix-parent-suffix (like un-believe-able).
prefix: what are the substituents?
parent: how many carbons?
suffix: what is the family of compounds?

 Practice Questions

1. This molecule is named 2-chlorobutane.

Cl
Figure 1.5.2 : 2-chlorobutane
What is the name of Molecule A?

Br
Figure 1.5.3 : Molecule A
2. This molecule is named 2-fluoro-3-methylpentane.

Figure 1.5.4 : 2-fluoro-3-methylpentane

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

I
Figure 1.5.5 : 4-iodo-2-methylhexane
What is the name of Molecule B?

1.5.1 [Link]
 Cl
Figure 1.5.6 : Molecule B
3. This molecule is named 1-chloro-2-butene.

Cl
Figure 1.5.7 : 1-chloro-2-butene
This molecule is named 5-fluoro-2-hexene.

F
Figure 1.5.8 : 5-fluoro-2-hexene
What is the name of Molecule C?

I
Figure 1.5.9 : Molecule C
4. This molecule is named 5-fluoro-1,3-cyclohexadiene.
F

Figure 1.5.10 : 5-fluoro-1,3-cyclohexadiene

What is the name of Molecule D?
Br

Figure 1.5.11 : Molecule D

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

This page titled 1.5: Halogens is shared under a CC BY 4.0 license and was authored, remixed, and/or curated by Rebekah O'Donnell (OpenStax
CNX) .

1.5.2 [Link]
1.6: Benzene and Conjugation
 Learning Objective
Understanding and naming benzene derivatives.

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

Figure 1.6.1 : benzene

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

Figure 1.6.2 .
This surprising stability of the double bonds in the benzene ring is not due to the cyclic arrangement of the carbon chain. Under the
appropriate reaction conditions, we see the following results for adding hydrogen across the double bonds of the molecules below.

+ H H

H H
+ H H

H H
+ H H
H H

Figure 1.6.3 .
Measuring the bond lengths gives the following result.

Bond Type Bond Length (Angstroms)

Single 1.54

Double 1.34

Benzene 1.4

Therefore, the three “double bonds” of the benzene ring are not true double bonds. The electrons are shared across all of the
carbons in the ring, an arrangement called conjugation which is better represented by the below structure.

Figure 1.6.4 .
When depicting benzene rings using the double bond drawing, remember that the ring is a hybrid between two equally likely
resonance structures.

Figure 1.6.5 .
Therefore both structures below would be named 1-chlorobenzene.
Cl
Cl

Figure 1.6.6 : 1-chlorobenzene

1.6.1 [Link]
When a benzene ring has two substituents, they are named based upon their position to each other rather than by numbers.
Cl
Cl

Figure 1.6.7 . o is for ortho, with substituents at 1,2:o-dichlorobenzene

Cl

Figure 1.6.8 . m is for meta, with substituents at 1,3:m-chloromethylbenzene

Cl

F
Figure 1.6.9 . p is for para, with substituents at 1,4:p-chlorofluorobenzene

 Practice Questions

1. What is the name of Molecule A?

Cl
Figure 1.6.10 : Molecule A
2. A benzene ring can be a substituent.
The name of this molecule is 2-phenyldecane.

Figure 1.6.11 : 2-phenyldecane

What is the name of Molecule B?

Figure 1.6.12 : Molecule B

Conjugation is not limited to cyclic structures. One of the two molecules below does not react with halogen 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 1.6.13 .

 Practice Questions
1. Write the steps that you use to name a benzene derivative or a molecule containing a benzene ring as a substituent, in order,
as instructions for a student who doesn't know how to do it.
2. Draw any benzene-containing molecule and go through the steps in naming your molecule.

This page titled 1.6: Benzene and Conjugation is shared under a CC BY 4.0 license and was authored, remixed, and/or curated by Rebekah
O'Donnell (OpenStax CNX) .

1.6.2 [Link]
1.7: Alcohols
 Learning Objective
How to name alcohols and phenols.

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.

 Practice Questions

1. The name of this molecule is ethanol.

OH
Figure 1.7.1 : ethanol
What is the name of Molecule A?
OH
Figure 1.7.2 : Molecule A
2. This molecule is named 2-butanol.

OH
Figure 1.7.3 : 2-butanol
This molecule is named 6-isopropyl-5-nonanol. Number the carbons.
OH

Figure 1.7.4 : 6-isopropyl-5-nonanol

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

Figure 1.7.5 : Molecule B

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

OH
Figure 1.7.6 : 3-propyl-2-octanol
4. Number the carbons. What is the name of molecule C?
HO

Figure 1.7.7 : Molecule C

5. This molecule is named 3-fluorocyclohexanol. Number the carbons.
OH

F
Figure 1.7.8 : 3-fluorocyclohexanol
6. Number the carbons. What is the name of Molecule D?
Molecule D

1.7.1 [Link]
 OH
Cl

Figure 1.7.9 .
7. This molecule is named 4-hexen-2-ol. Number the carbons.

OH
Figure 1.7.10 : 4-hexen-2-ol
8. Number the carbons. What is the name of Molecule E?
OH

Figure 1.7.11 : Molecule E

9. This molecule is named 2,3-pentanediol.
OH

OH
Figure 1.7.12 : 2,3-pentanediol
What is the name of Molecule F?
OH OH

OH
Figure 1.7.13 : Molecule F

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

OH
HO

Figure 1.7.14 : Two phenols

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

Figure 1.7.15 : 2-chlorophenol / o-chlorophenol

 Practice Questions

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

OH

Figure 1.7.16 : Molecule G

2. What additions do we make to our existing naming rules to name alcohols?
3. 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.
4. Draw any alcohol and go through the steps in naming your molecule.

This page titled 1.7: Alcohols is shared under a CC BY 4.0 license and was authored, remixed, and/or curated by Rebekah O'Donnell (OpenStax
CNX) .

1.7.2 [Link]
1.8: Ethers
 Learning Objective
How to name ethers.

In organic chemistry, any alkyl group can be abbreviated as R. An ether, in which the carbons of two alkyl 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 IUPAC name is ethoxyethane.
O
Figure 1.8.1 : ethoxyethane
The common name of this molecule is ethyl methyl ether, and its IUPAC name is methoxyethane.
H3C
O

Figure 1.8.2 : methoxyethane

 Practice Questions

1. What are the common and IUPAC names of Molecule A?

O

Figure 1.8.3 : Molecule A

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

O
CH3

Figure 1.8.4 : 2-methoxy-3-methylbutane

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

O
CH3

Figure 1.8.5 : Molecule B

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

O
Figure 1.8.6 : 4-butoxy-2-butanol
5. Number the carbons. What is the name of Molecule C?
OH

Figure 1.8.7 : Molecule C

6. What additions do we make to our existing naming rules to name ethers?
7. 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.
8. Draw any ether and go through the steps in naming your molecule.

This page titled 1.8: Ethers is shared under a CC BY 4.0 license and was authored, remixed, and/or curated by Rebekah O'Donnell (OpenStax
CNX) .

1.8.1 [Link]
1.9: Aldehydes and Ketones
 Learning Objective
How to name aldehydes and ketones.

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

R H
Figure 1.9.1 . The R group can also be a hydrogen: aldehyde
O

R R1

Figure 1.9.2 . The R groups can be the same or different: ketone

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

Figure 1.9.3 : C3H6O

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

H H
Figure 1.9.4 : methanal
The name of this molecule is butanal.
H

Figure 1.9.5 : butanal

 Practice Questions

1. What is the name of Molecule A?

H

O
Figure 1.9.6 : Molecule A
2. This molecule is named 5-methylhexanal. Number the carbons.
H

Figure 1.9.7 : 5-methylhexanal

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

Figure 1.9.8 : Molecule B

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

Figure 1.9.9 : 3-ethyl-4-methylhexanal

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

1.9.1 [Link]
 H
Cl
O

Figure 1.9.10 : Molecule C

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

O
Figure 1.9.11 : 3-pentenal
7. Number the carbons. What is the name of Molecule D?
H

O
Figure 1.9.12 : Molecule D
8. A well-known ketone is 2-propanone, commonly known as acetone, and used as a nail polish remover.
O

Figure 1.9.13 : 2-propanone

This molecule is named 2-pentanone.
O

Figure 1.9.14 : 2-pentanone

What is the name of Molecule E?
O

Figure 1.9.15 : Molecule E

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

Figure 1.9.16 : 5-ethyl-2-heptanone

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

Figure 1.9.17 : Molecule F

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

Cl

Figure 1.9.18 : 6-chloro-4-ethyl-3-heptanone

12. Number the carbons. What is the name of Molecule G?
O
I

Figure 1.9.19 : Molecule G

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

Br
Figure 1.9.20 : 3-bromocyclohexanone
14. Number the carbons. What is the name of Molecule H?

1.9.2 [Link]
 O

Cl
Figure 1.9.21 : Molecule H
15. The name of this molecule is 4-hydroxy-2-butanone. Number the carbons.
O

OH
Figure 1.9.22 : 4-hydroxy-2-butanone
16. Number the carbons. What is the name of Molecule I?
O

OH
OH

Figure 1.9.23 : Molecule I

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

O
O
Figure 1.9.24 : 5-chloro-4-oxohexanal
18. Number the carbons. What is the name of Molecule J?
O H

O
OH
Figure 1.9.25 : Molecule J
19. What additions do we make to our existing naming rules to name aldehydes and ketones?
20. 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.
21. Draw any aldehyde or ketone and go through the steps in naming your molecule.

This page titled 1.9: Aldehydes and Ketones is shared under a CC BY 4.0 license and was authored, remixed, and/or curated by Rebekah
O'Donnell (OpenStax CNX) .

1.9.3 [Link]
1.10: Carboxylic acids and Esters
 Learning Objective
How to name carboxylic acids and esters.

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

R OH
Figure 1.10.1 : carboxylic acid
O
R1
R O

Figure 1.10.2 : ester

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

Figure 1.10.3 : acetic acid and benzoic acid

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

Figure 1.10.4 : pentanoic acid

 Practice Questions

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

Figure 1.10.5 : Molecule A

2. The name of this molecule is hexanedioic acid.
O
OH
HO
O
Figure 1.10.6 : hexanedioic acid
What is the name of Molecule B?
O O

HO OH
Figure 1.10.7 : Molecule B
3. The name of this molecule is cyclohexanecarboxylic acid.
O

OH

Figure 1.10.8 : cyclohexanecarboxylic acid

What is the name of Molecule C?

O
OH
Figure 1.10.9 : Molecule C

1.10.1 [Link]
 4. The name of this molecule is 1,2-benzenedicarboxylic acid.
O OH
O

OH

Figure 1.10.10: 1,2-benzenedicarboxylic acid

What is the name of Molecule D?
O OH
O

OH

O OH
Figure 1.10.11: Molecule D
5. The name of this molecule is 4-bromopentanoic acid. Number the carbons.
O

OH
Br
Figure 1.10.12: 4-bromopentanoic acid
6. Number the carbons. What is the name of Molecule E?
Molecule E

OH

Figure 1.10.13.
7. This molecule is named 2-hydroxybutanoic acid (also known as lactic acid).
OH
OH

Figure 1.10.14: 2-hydroxybutanoic acid

What is the name of Molecule F?
OH
HO OH

O O

Figure 1.10.15: Molecule F

8. This molecule is named 3,6-dioxo-4-hydroxyhexanoic acid.
O O
O
OH
H OH
Figure 1.10.16: 3,6-dioxo-4-hydroxyhexanoic acid
What is the name of Molecule G?
OH
O

OH O
Figure 1.10.17: Molecule G

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

O O

H
Figure 1.10.18: isobutyl methanoate
The process of esterification involves adding an alcohol to a carboxylic acid in the presence of hydrogen ions.

1.10.2 [Link]
 O H+ O
+ R1
HO R1
R OH O

Figure 1.10.19: esterification

To name an ester, first we name the alcohol used, and then the carboxylic acid. Below is shown the esterification reaction of
ethanol and propanoic acid to create ethyl propanoate.
O H+ O
+ HO
OH O

Figure 1.10.20: synthesis of ethyl propanoate

 Practice Questions

1. What is the name of Molecule H?

O
CH3
O
Figure 1.10.21: Molecule H
2. What is the name of Molecule I?
O

Figure 1.10.22: Molecule I

3. This molecule is named dimethylbutanedioate.
O
H3C O
O CH3
O
Figure 1.10.23: dimethylbutanedioate
What is the name of Molecule J?
O O

O O

Figure 1.10.24: Molecule J

4. This molecule is named 2-chloroethyl propanoate.
O
Cl
O
Figure 1.10.25: 2-chloroethyl propanoate
What is the name of Molecule K?
O

O
I
Figure 1.10.26: Molecule K
5. This molecule is named 2-bromopropyl 4-chlorobutanoate. Number the carbons.
Br
O
Cl
O
Figure 1.10.27: 2-bromopropyl 4-chlorobutanoate
6. Number the carbons. What is the name of Molecule L?
O

O Cl
I
Figure 1.10.28: Molecule L
7. What additions do we make to our existing naming rules to name carboxylic acids and esters?
8. 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.
9. Draw any carboxylic acid and go through the steps in naming your molecule.

1.10.3 [Link]
 10. 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.
11. Draw any ester and go through the steps in naming your molecule.

This page titled 1.10: Carboxylic acids and Esters is shared under a CC BY 4.0 license and was authored, remixed, and/or curated by Rebekah
O'Donnell (OpenStax CNX) .

1.10.4 [Link]
1.11: Amines and Amides
 Learning Objective
How to name amines and amides.

An amino group consists of a nitrogen atom bonded to two hydrogen atoms, written as -NH2. If the hydrogens are replaced by R
groups, the group is referred to as a substituted amino group. Amines and 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 substitution of the amino group. For
example, an amine in which all three of the potential nitrogen bonds are with R groups instead of hydrogens is called a tertiary
amine (see the right-most molecule below).
H
N N
H2 N

Figure 1.11.1 : primary, secondary, and tertiary amines

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

NH2

Figure 1.11.2 : an enormous primary amine

There are multiple substitutive nomenclatures for naming amines, with the two most common being IUPAC and Chemical Abstract
Service. Both will be described below.
This molecule is named 2-pentanamine (CAS) or 2-aminopentane (IUPAC).

H2N

Figure 1.11.3 : 2-pentanamine (CAS) / 2-aminopentane (IUPAC)

 Practice Questions

1. What are the names of Molecule A?

Molecule A

H 2N

Figure 1.11.4 .
2. This molecule is named 1,6-hexanediamine (CAS) or 1,6-diaminohexane (IUPAC).
NH2
H2N

Figure 1.11.5 : 1,6-hexanediamine (CAS) / 1,6-diaminohexane (IUPAC)

What are the names of Molecule B?
H 2N NH2

Figure 1.11.6 : Molecule B

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

Figure 1.11.7 .
What are the names of Molecule C?

1.11.1 [Link]
 H
N

Figure 1.11.8 : Molecule C

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

NH2 O

Figure 1.11.9 : 4-amino-2-pentanone (CAS) / 4-aminopentane-2-one (IUPAC)

5. Number the carbons. What are the names of Molecule D?
H 2N

OH
Figure 1.11.10: Molecule D
6. This molecule is named 2-(N-methylamino)ethanol (CAS) or 2-methylaminoethanol (IUPAC). Number the carbons.
OH
N
H

Figure 1.11.11: 2-(N-methylamino)ethanol (CAS) / 2-methylaminoethanol (IUPAC)

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

N OH

Figure 1.11.12: Molecule E

An amide is a carboxylic acid derivative in which the carboxyl -OH has been replaced with an amino or substituted amino
group. Amides are also described as primary, secondary, or tertiary depending on the number of R groups bound directly to the
nitrogen.
O
O O
1
R1
R R N
R NH2 R N
H R2

Figure 1.11.13: primary, secondary, and tertiary amides

The naming of simple amides is based on the carboxylic acid nomenclature, and keeps the same name in the CAS and IUPAC
systems.
The name of this molecule is 3-methylbutanamide.
O

NH2

Figure 1.11.14: 3-methylbutanamide

 Practice Questions

1. What is the name of Molecule F?

Molecule F
O

NH2
Cl
Figure 1.11.15.
2. The name of this molecule is N-methylbenzamide.
O

N
H

Figure 1.11.16: N-methylbenzamide

What is the name of Molecule G?

1.11.2 [Link]
 H
N

Cl
Figure 1.11.17: Molecule G
3. What additions do we make to our existing naming rules to name amines and amides, in the substitutive naming system that
you use?
4. Write the steps that you use to name an amine in order, as instructions for a student who doesn't know how to do it.
5. Draw any amine and go through the steps in naming your molecule.
6. 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.
7. Draw any amide and go through the steps in naming your molecule.

This page titled 1.11: Amines and Amides is shared under a CC BY 4.0 license and was authored, remixed, and/or curated by Rebekah O'Donnell
(OpenStax CNX) .

1.11.3 [Link]
Index
A C ether naming
acetone carbon atoms 1.8: Ethers
1.9: Aldehydes and Ketones 1.1: Unbranched Alkanes ethoxyethane
acid derivatives carbon chain 1.8: Ethers
1.10: Carboxylic acids and Esters 1.2: Constitutional Isomers ethyl
aldehyde examples carbon numbering 1.3: Alkyl Substituents
1.9: Aldehydes and Ketones 1.8: Ethers ethyl methyl ether
alkanes 1.9: Aldehydes and Ketones 1.8: Ethers
1.1: Unbranched Alkanes carbonyl group
1.2: Constitutional Isomers 1.9: Aldehydes and Ketones F
1.3: Alkyl Substituents 1.10: Carboxylic acids and Esters fluorine
alkene examples carboxy group 1.5: Halogens
1.4: Alkenes and Alkynes 1.10: Carboxylic acids and Esters formaldehyde
alkene naming carboxylic acid derivative 1.9: Aldehydes and Ketones
1.4: Alkenes and Alkynes 1.11: Amines and Amides functional groups
alkyl groups carboxylic acids 1.4: Alkenes and Alkynes
1.3: Alkyl Substituents 1.10: Carboxylic acids and Esters 1.10: Carboxylic acids and Esters
1.8: Ethers Chemical Abstract Service
alkyl halide 1.11: Amines and Amides G
1.5: Halogens chemical nomenclature general formula
alkyl substituents 1.5: Halogens 1.1: Unbranched Alkanes
1.3: Alkyl Substituents 1.9: Aldehydes and Ketones
Group 7A elements
alkyne examples chemical stability 1.5: Halogens
1.4: Alkenes and Alkynes 1.6: Benzene and Conjugation
alkyne naming chemistry education H
1.4: Alkenes and Alkynes 1.1: Unbranched Alkanes
amides chlorine halogenated hydrocarbons
1.5: Halogens
1.11: Amines and Amides 1.5: Halogens
amines cis/trans isomers halogens
1.5: Halogens
1.11: Amines and Amides 1.4: Alkenes and Alkynes
aromatic chemistry condensed structural formulas heptane
1.1: Unbranched Alkanes
1.6: Benzene and Conjugation 1.1: Unbranched Alkanes
1.2: Constitutional Isomers
aromatic hydrocarbons condensed structure heptanone
1.6: Benzene and Conjugation 1.3: Alkyl Substituents
1.9: Aldehydes and Ketones
conjugation hexane
B 1.6: Benzene and Conjugation
1.1: Unbranched Alkanes
benzene derivatives constitutional isomers 1.2: Constitutional Isomers
1.6: Benzene and Conjugation 1.2: Constitutional Isomers hydrocarbons
1.9: Aldehydes and Ketones
benzene ring 1.1: Unbranched Alkanes
1.6: Benzene and Conjugation
cycloalkanes 1.4: Alkenes and Alkynes
boiling point trends 1.3: Alkyl Substituents hydrogen atoms
1.1: Unbranched Alkanes
cyclohexanone 1.1: Unbranched Alkanes
boiling points 1.9: Aldehydes and Ketones hydroxy group
1.1: Unbranched Alkanes 1.10: Carboxylic acids and Esters
bonding arrangements D
1.2: Constitutional Isomers decane I
branched molecules 1.1: Unbranched Alkanes iodine
1.3: Alkyl Substituents diethyl ether 1.5: Halogens
branching in alkanes 1.8: Ethers isomerism
1.2: Constitutional Isomers double bonds 1.2: Constitutional Isomers
bromine 1.6: Benzene and Conjugation 1.4: Alkenes and Alkynes
1.5: Halogens isomers
butanal E 1.3: Alkyl Substituents
1.9: Aldehydes and Ketones ester synthesis IUPAC naming
butane 1.10: Carboxylic acids and Esters 1.3: Alkyl Substituents
1.8: Ethers
1.1: Unbranched Alkanes esterification
IUPAC nomenclature
butyl 1.10: Carboxylic acids and Esters
1.5: Halogens
1.3: Alkyl Substituents esters
1.10: Carboxylic acids and Esters
ethane
1.1: Unbranched Alkanes

1 [Link]
K naming instructions practice questions
ketone examples 1.6: Benzene and Conjugation 1.1: Unbranched Alkanes
1.9: Aldehydes and Ketones naming ketones 1.3: Alkyl Substituents
1.5: Halogens
1.9: Aldehydes and Ketones
1.6: Benzene and Conjugation
M naming steps primary amine
1.3: Alkyl Substituents
meta 1.11: Amines and Amides
1.6: Benzene and Conjugation
nomenclature propane
1.3: Alkyl Substituents
methanal 1.10: Carboxylic acids and Esters
1.1: Unbranched Alkanes
1.9: Aldehydes and Ketones
Nomenclature of Aldehydes & Ketones propanone
methane 1.7: Alcohols
1.9: Aldehydes and Ketones
1.1: Unbranched Alkanes
nonane propyl
methoxyethane 1.1: Unbranched Alkanes
1.3: Alkyl Substituents
1.8: Ethers
methyl O R
1.3: Alkyl Substituents
octane resonance structures
molecular formula 1.6: Benzene and Conjugation
1.1: Unbranched Alkanes
1.2: Constitutional Isomers
organic chemistry
molecular formulas
1.1: Unbranched Alkanes
S
1.1: Unbranched Alkanes 1.2: Constitutional Isomers saturated hydrocarbons
molecular nomenclature 1.4: Alkenes and Alkynes 1.1: Unbranched Alkanes
1.5: Halogens
1.11: Amines and Amides
1.8: Ethers
secondary amine
molecular structure 1.10: Carboxylic acids and Esters 1.11: Amines and Amides
1.4: Alkenes and Alkynes
organic molecule identification structural formula
1.5: Halogens
1.8: Ethers 1.2: Constitutional Isomers
1.6: Benzene and Conjugation
1.10: Carboxylic acids and Esters organic molecules structural isomers
molecular structures 1.3: Alkyl Substituents 1.2: Constitutional Isomers
1.9: Aldehydes and Ketones ortho substituents
molecule naming practice 1.6: Benzene and Conjugation 1.5: Halogens
1.6: Benzene and Conjugation
1.8: Ethers
P substituted amino group
1.11: Amines and Amides
N para substitution levels
naming aldehydes 1.6: Benzene and Conjugation
1.11: Amines and Amides
1.9: Aldehydes and Ketones pentane
naming compounds 1.1: Unbranched Alkanes
1.6: Benzene and Conjugation 1.2: Constitutional Isomers
T
naming conventions pentanone tertiary amine
1.9: Aldehydes and Ketones 1.11: Amines and Amides
1.11: Amines and Amides
naming ethers steps phenyldecane
1.8: Ethers 1.6: Benzene and Conjugation U
naming hydrocarbons positional isomers unbranched alkanes
1.5: Halogens 1.4: Alkenes and Alkynes 1.1: Unbranched Alkanes
unsaturated hydrocarbons
1.4: Alkenes and Alkynes

2 [Link]
Glossary
Sample Word 1 | Sample Definition 1

1 [Link]
Detailed Licensing
Overview
Title: Organic Chemistry Nomenclature Workbook (O'Donnell)
Webpages: 22
All licenses found:
CC BY 4.0: 54.5% (12 pages)
Undeclared: 45.5% (10 pages)

By Page
Organic Chemistry Nomenclature Workbook (O'Donnell) - 1.5: Halogens - CC BY 4.0
CC BY 4.0 1.6: Benzene and Conjugation - CC BY 4.0
Front Matter - Undeclared 1.7: Alcohols - CC BY 4.0
TitlePage - Undeclared 1.8: Ethers - CC BY 4.0
InfoPage - Undeclared 1.9: Aldehydes and Ketones - CC BY 4.0
Table of Contents - Undeclared 1.10: Carboxylic acids and Esters - CC BY 4.0
Licensing - Undeclared 1.11: Amines and Amides - CC BY 4.0

1: Chapters - Undeclared Back Matter - Undeclared

1.1: Unbranched Alkanes - CC BY 4.0 Index - Undeclared

1.2: Constitutional Isomers - CC BY 4.0 Glossary - Undeclared
1.3: Alkyl Substituents - CC BY 4.0 Detailed Licensing - Undeclared
1.4: Alkenes and Alkynes - CC BY 4.0

1 [Link]