Nomenclature
Basic Nomenclature
n-Alkanes are the Simplest Organic Compounds
The straight-chain alkanes make up a family of hydrocarbons that have the general formula: H−(CH2)n−H or
CnH2n+2.
Alkanes are sometimes called saturated hydrocarbons. This term means that the carbon skeleton is “saturated”
with hydrogen (attached to the MAXIMUM number of hydrogens). In saturated hydrocarbons there are only single
bonds: each carbon has a tetrahedral shape (sp3 hybridized).
methane CH4 Tetrahedral: H Same plane as page
109.5o
methyl alcohol or wood alcohol C H into page
Greek methy (wine) hyle (wood) H H
Same plane as page
out of page
H H
ethane C 2H 6 CH3-CH3 ball and stick
H C C
Greek- aithein “to kindle or blaze” H
H H
propane C3H8 CH3-CH2-CH3 H H
H H
Taken from Propionic acid C
C C
Greek proto (first) and pion (fat) H H 1
H H
butane CH3-(CH2)2-CH3 C4H10
Taken from butyric acid
odorous component of rancid butter Latin butyrum (butter) 2
4
1
each vertex and end is a carbon with 3
the appropriate number of hydrogens
pentane CH3-(CH2)3-CH3 C5H12
Greek
hexane CH3-(CH2)4-CH3 C6H14
Greek
heptane CH3-(CH2)5-CH3 C7H16
Greek
octane CH3-(CH2)6-CH3 C8H18
Greek
nonane CH3-(CH2)7-CH3 C9H20
Latin
decane CH3-(CH2)8-CH3 C10H22
Greek
Stick Structures 2
Shown below is the progression for drawing line structures. Note that hydrogens bonded to carbons are not drawn;
however, hydrogens bonded to heteroatoms are. Heteroatoms refer to atoms other than carbon such as oxygen or
nitrogen. Lone pairs of electrons on heteroatoms are typically not drawn either.
Classification of Carbons and Hydrogens
Primary (1o) is an sp3 carbon bonded to one other carbon
Secondary (2o) is an sp3 carbon bonded to two other carbons
Tertiary (3o) is an sp3 carbon bonded to three other carbons
Quaternary (4o) is an sp3 carbon bonded to four other carbons
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Alkane Substituents/Branches
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Nomenclature of Branched-Chain Alkanes (IUPAC)
What is the name of the following compound?
1) Find the longest continuous chain (the parent chain), which may or may not be shown in a straight line
and name this chain
2) Number the parent chain from one end in such a way that the smaller number is used at the first point of
difference.
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3) Name each substituent/branch group that is attached to this parent chain.
6 3
4 2
7 5 1
4) Alphabetize the substituent/branch groups.
5) Assign to each substituent/branch group a number signifying its point of attachment to the parent chain (if
more than one of the same add the following prefix: 2 = di, 3 = tri, 4 = tetra, etc.).
6) Numbers are separated by commas and number and names are separated by a dash.
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When two chains of equal length compete to be parent, choose the chain with the greatest number of substituents
When branching first occurs at an equal distance from either end of the parent chain, choose the name that gives the
lower number at the first point of difference
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Common Branched Alkyl Groups
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Alkenes and Alkynes
CH3-CH3 CH2=CH2 CHΞCH
Ethane ethene ethyne
Common Name: ethylene acetylene
C CH
5-chloro-4-ethyl-6-methyl-2-heptene
or IUPAC: phenylethyne 2-pentyne
Trivial (older): phenylacetylene ethylmethylacetylene
5-chloro-4-ethyl-6-methylhept-2-ene
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Functional Groups
isopropyl
alkene
isobutyl
alkyne
ether vinyl
sec-butyl
allyl
aryl
tert-butyl
alkane
benzyl
neopentyl 10
Nomenclature Priorities of Selected Functional Groups
Partial Structure Name
R-COOH -oic acid
R-COOR -oate
R-CONH2 -amide
increasing R-C≡N -nitrile
priority R-CHO -al
R-CO-R -one
R-OH -ol
R-NH2 -amine
R2C = CR2 -ene
RC≡CR -yne
R-O-R, C6H5-, Cl-, Br-, NO2- etc ether, phenyl, halo, nitro
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Question 1.1: Draw the following structures:
3,6-diethyl-2,7-dimethyloctane 4-(1-methylethyl)-6-methyldecane
What’s another name could you give this molecule?
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3-chloro-5-methyl-1-cyclohexene
5-chloro-3-ethyl-4-methylhexan-3-ol
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7-chloro-5-ethyl-3-hydroxy-6-methyloctan-4-one
4-hydroxypentanoic acid
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Question 1.2: How many carbons does the following molecule have?
O a) 12
b) 13
c) 14
d) 15
e) 16
Question 1.3: How many hydrogens does the above molecule have?
(Remember each carbon has four bonds)
A) 13 B) 14 C) 15 D) 16 E) 17 O
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Question 1.4: How many 2° carbon atoms does the following molecule have?
Question 1.5: Match the following compounds with their functional group:
A) 1 – a, 3 – b, 4 – c
B) 3 – a, 2 – b, 1 – c
a) CH3CH2CHO
C) 2 – a, 3 – b, 4 – c
b) CH3COCH3
D) 4 – a, 1 – b, 2 – c
c) CH3OCH3
E) 1 – a, 2 – b, 3 – c
1) alcohol
2) aldehyde
3) ketone
4) ether
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Tasks Before Next Lecture
• Review material from first-year (LEARN → Content → Lecture Materials → First Year Review)
• Learn nomenclature: it takes practice!!
• Read course notes
• Create a nomenclature summary
• Practice problems:
• Course notes (LEARN → Content → Lecture Materials → Week 1)
• Worksheets (LEARN → Content → Extra Practice Questions and Worksheets)
• Course Textbook
• Prepare for lecture’s next week (watch pre-lecture video, read notes as needed, complete pre-lecture
quiz)
• Want to be better at time management this term? Create a study plan for the entire term, including your
class/lab schedule, all assignment/quiz/lab report due dates, lecture and lab preparation time, lecture
review time, etc. Build in flexibility for busier weeks and time for yourself!
LEARN → Content → Study Plans
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