1. Alkanes CnH2n+2
ALKANES are compounds that contain only carbon-carbon and carbon-
hydrogen single bonds.
The title shows the general formula for a chain alkane. The
first ten alkanes are:
METHane CH4 HEXane C6H14
ETHane C2H6 HEPTane C7H16
PROPane C3H8 OCTane C8H18
BUTane C4H10 NONane C9H20
PENTane C5H12 DECane C10 H22

2. Lewis dot vs condensed formulas: propane.
H H H
H C C C H CH3CH2CH3
H H H
Terminal carbons condense to CH3 with the hydrogens usually to
the right of the carbon. Interior carbons condense to CH2.

3. Branching
A branch or substituents on a chain may be condensed into the
chain usually after the carbon from which it branches.
CH3CH(CH3)CHClCH2CH3
H
HCH
H H H H
H C C C C C H
H H Cl H H

4. NOMENCLATURE
Alkyl Groups
H H
H C H H C or CH3
H H
An alkyl group is an alkane with one hydrogen atom removed. It is
named by replacing the -ane of the alkane name with -yl.
e.g. Methane becomes a methyl group.

5. For PROPANE, removal of a hydrogen generates two different
propyl groups depending on whether an end or center H is
removed.
CH3 CH2 CH3
CH3CH2CH2 CH3CH CH3
n-propyl isopropyl

6. For BUTANE, gives two butyl groups depending on whether an end
(1o) or interior (2o) H is removed.
CH3 CH2 CH2 CH3
CH3 CH2 CH2 CH2 CH3 CH CH2 CH3
n-butyl sec-butyl

7. ISOBUTANE gives two butyl groups depending on whether a 10 or
30 H is removed.
CH3
CH3 CH CH3
CH3 CH3
1o 3o
CH3 CH CH2 CH3 C CH3
isobutyl tert-butyl

8. NOMENCLATURE
1. The base or parent name for an alkane is determined by the
longest chain of carbon atoms in the formula. Note: the
longest chain may bend and twist. It is seldom horizontal!
– Any carbon groups not part of the base chain are called branches
or substituents.
– These carbon groups are also called alkyl groups.
A CH3
CH2CH2CH CH2CH3
B CH3
CH2
CH3CH2CH2 CH2
CH3
CH3CH2CH CH2CH CH3
A. 7 carbons
B. 8 carbons

9. 2. Number the carbon atoms in the chain starting from the end with
the first branch. If both branches are equally from the ends,
continue until a point of difference occurs.
1 CH3
6 7 8
CH3 2 CH2 CH2CH2CH3
4
5 CH2CH2CH CH2CH3 CH3CH CH2CH CH2CH3
3 2 1 3 4 5 6 7
6 CH2
this branch would be on C-4
7 CH3 if you started at correct C-8

10. 3. Prefix the branches/substituents in alphabetical order before the
base/stem name (longest chain). Halogens usually come first.
- Indicate the position of the branch on the main chain by prefixing its
name with the carbon number to which it is attached. Separate
numbers and letters with a hyphen.
CH3
CH2 CH3
CH3 CH2 CH CH2 CH CH3
4-ethyl-2-methylhexane

11. - Hyphenated and number prefixes are not considered when
alphabetizing groups.
5-sec-butyl-4-isopropylnonane
CH3
CH3 CH CH2 CH3
CH CH CH CH2 CH2 CH2 CH3
CH3 CH2 CH2 CH3

12. - When a branch/substituents occurs more than once, prefix the
name with di-, tri-, tetra-, etc. Then prefix the number to the name
with a separate number for each occurrence. Separate numbers
with commas.
CH3 CH2CH3
CH3CH CH CH2CH CH2CH3
CH3
5-ethyl-2,3-dimethylheptane
NOTE: ethyl > dimethyl

13. CH3 CH3CH CH3
CH2 CH2
CH3C CH2CH2C CH2CH3
CH3 CH2CH2CH2CH3
6-isobutyl-6-ethyl-3,3-dimethyldecane

14. Alkenes and Alkynes
• ALKENES are compounds that have carbon-carbon double bond
framework. With the general formula of, CnH2n. Simplest alkene: ethene
(ethylene) C2H4
• ALKYNES have one or more carbon-carbon triple bonds. Simplest alkyne:
ethyne (acetylene) C2H2

15. NOMENCLATURE
Base name from longest chain containing the multiple bond.
Change -ane to -ene or -yne.
Number from the end that will give the first carbon of the multiple
bond the lower number.
Prefix the name with the number of the first multiple bond carbon.
Prefix branch/substituent names as for alkanes.
CH3 CH2 CH3
3-ethyl-6-methyl-3-heptene CH3 CH CH2 CH C
CH2 CH3
2-bromo-3-hexyne CH3CH C C CH2CH3
Br

16. Cyclic alkenes are named like cyclic alkanes. Prefix name with
cyclo-.
Numbering MUST start at one end of the double bond and go
THROUGH the bond.
Substituents must have the lower possible numbers.
CH2 CH3
Cl
CH CH
5-chloro-3-methylcyclohexene
CH2 CH
CH

17. ALCOHOLS AND PHENOLS
Alcohols are classified as primary (1°), secondary (2°), or tertiary
(3°) depending on the number of carbon groups bonded to the
hydroxyl bearing carbon.
CH3CH2OH Primary:
ONE R group on the carbon attached to -OH
CH3CH CH3 Secondary:
OH TWO R groups on the carbon attached to -OH
CH3 Tertiary:
THREE R groups on the carbon attached to -OH
CH3 C CH3
OH

18. ALCOHOLS AND PHENOLS
NOMENCLATURE
Alcohols are classified as primary (1o), secondary (2o), or tertiary, depending on
the numbers of carbon substituents bonded to the hydroxyl-bearing carbon:
STEP 1 Select the longest chain containing the hydroxyl and replace
the –e ending of the corresponding parent with –ol
STEP 2 Number the carbons of the parent chain beginning at the
end nearer the hydroxyl
STEP 3 Number all substituents according to their position on the
chain, and write the name listing the substituents in
alphabetical order.

19. ETHERS
NOMENCLATURE
Common names for ethers consist of the names of the two groups attached
to the O listed in alphabetical order (or size) and followed by ‘ether’. Each
part is a separate word
O
CH3
CH3CH – O – CH3
Isopropyl methyl ether Ethyl phenyl ether
The IUPAC names for ethers are based on the alkane name of the longest
chain attached to the O. The shorter chain is named as an alkoxy
substituent. (alkane with the ane replaced by oxy, eg. CH3CH2O = ethoxy).
The longest chain will be the parent structure (-ane).
CH3CH2CH2CH2CH2-O-CH3 1-methoxypentane methyl pentyl ether
CH3CH2-O-CH2CH2CH2CH3 1-ethoxybutane ethyl butyl ether

20. THIOLS
Thiols (mercaptans), R-SH, are sulfur analogs of alcohols, and sulfides, RSR’,
are sulfur analogs of ether.
The SH group is variously called the thiol group, the mercaptan group, or the
sulfuhydryl group.
NOMENCLATURE
Name based on the longest alkane chain with the suffix
position indicated by a number.
3D
CH3
CH3 – CH - CH2 – CH2
SH
3-methyl-1-butanethiol

21. CARBONYL COMPOUNDS
O
• contains the carbonyl group, C=O
R C R
Aldehydes: O
R may be hydrogen usually a
carbon containing group R C H RCHO
O
Ketones:
R contains carbon RC R RCOR

22. Aldehydes
NOMENCLATURE
STEP 1 Select the longest carbon chain containing the carbonyl
carbon.
STEP 2 The -e ending of the parent alkane name is replaced by the
suffix -al.
STEP 3 The carbonyl carbon is always numbered “1.” (It is not
necessary to include the number in the name.)
STEP 4 Name the substituents attached to the chain in the usual way.
O O 4
O 3 2
CH3CH CH3CH2CH CH3CH CH2CH2CH
Ethanal Propanal H2C
5 CH
1
(Acetaldehyde) (Propionaldehyde) 3 6
4-methylhexanal

23. KETONES
NOMENCLATURE
STEP 1 Naming the two alkyl groups attached to the carbonyl in
a) alphabetical order or b) by increasing size.
O Methyl ethyl ketone
or
CH3 C CH2 CH3
Ethyl methyl ketone
STEP 2 Longest chain with the C=O. The corresponding alkane
is (-e) is replaced with -one
STEP 3 The position of C=O by number of chain is indicated.
Cl O
4-chloro-2-pentanone
CH3CH CH2C CH3

24. CARBOXYLIC ACIDS
O O
C OH or -CO2H or -COOH S OH or -SO3H
carboxyl group
O sulfonic acid
group
O
R = may be H,
R C OH alkyl,or aromatic

25. NOMENCLATURE
Start numbering at the -COOH carbon. Replace the -e of the
alkane name with oic acid.
CH3 O
CH3 CH CH2 C OH
4 3 2 1
3-methylbutanoic acid

26. The Acid Derivatives
AMIDES
O R2 R1, R2, R3 may be
R1 C N H, alkyl, aryl
R3
ESTERS
O R2 should not
R1 C O R2 be H

27. ESTERS
Esters are derivatives of an ACID and an ALCOHOL that can also
be hydrolyzed to these parent compounds.
ESTER
LINKAGE
O
R = may be
R C OR alkyl,or aromatic

28. NOMENCLATURE
Name the alkyl group attached to the oxygen atom first. (Alcohol part of
the ester). Base name for the acid part of the structure from the longest
chain ending in the C=O. Change the oic acid of the acid name to oate
and add this to the name in 1 as a second word.
O
CH3CH2C O CH2CH3 ethyl propanoate

29. AMINES
NOMENCLATURE
• Primary amines are named in systematic (IUPAC) nomenclature by
replacing the -e of the corresponding parent alkane with -amine
• In common nomenclature they are named as alkylamines
• Simple secondary and tertiary amines are named in common nomenclature
by designating the organic groups separately in front of the word amine
• In systematic nomenclature, the smaller groups on the amine nitrogen are
designated as substituents and given the locant N

30. AMIDES
NOMENCLATURE
STEP 1 Names are derived from the acid.
STEP 2 Remove –ic acid (common) or –oic acid (IUPAC) and
replace with –amide.
STEP 3 Nitrogen substituents are prefixed to the name and
indicated by N.
O O
CH3C NH2 CH3CH2C NH CH3
ethanamide or acetamide N-methylpropanamide