Chem 31.

1 WFUV1
2nd Semester AY1920
Prepared by: Jasper S. Dumalaog
It is the chemistry of compounds that contain the element carbon with the
exception of simple compounds such as CO32-, CO2 and CO.
Carbon compounds are central to the structure of living organisms.

Carbon can form strong bonds with another carbon, hydrogen, nitrogen,
oxygen, sulfur.

ethanol

polypeptide
The atoms in organic compounds can form a fixed number of bonds using their
outermost shell (valence) electrons.

A carbon atom can use one or more of its valence electrons to form bonds with
other carbon atoms:
Organic compounds are chemical compounds which contains carbon that are
covalently linked to atoms of other elements, most commonly hydrogen,
oxygen, or nitrogen.

Around 2 million organic compounds have been isolated or characterized.

Classified into functional groups.

BOND-LINE STRUCTURE
ETHANOL

PARACETAMOL
• Corner or endpoint: C atom
• Line: bond
• Zigzag format: clear distinction of
corner or endpoint
• C-H bonds not drawn explicitly:
assume all C has enough H for a
complete octet
• Double bonds and triple bonds
• Triple bonds: sp-hybridized C →
linear geometry
• All other atoms are drawn explicitly
• PRACTICE → FAMILIARITY!
 C8H14 C6H10 C5H6N2

C4H9NO2 C9H11NO2 C10H16

 C29H50O2

C16H13ClN2O

C19H28O2
• Zigzag format
• Direction in which bonds are drawn
is irrelevant
• Draw bonds as far apart as possible
• Draw all heteroatoms (atoms other
than C and H) and all atoms
bonded to heteroatoms
• Never draw C atom with more than
4 bonds
• CONSIDER AESTHETIC APPEAL!
• Recall: VSEPR theory
• Dashed wedge: behind the
plane of the paper
• Solid wedge: out of the plane
of the paper
• Ordinary line: in the plane of
the paper

• General rule: draw as many C

atoms in the plane of the paper as
possible
Functional group: characteristic group of atoms/bonds that possess a predictable
chemical behavior
• Alkane – only single bonds between carbon atoms
• Alkene – at least one carbon-carbon double bond
• Alkyne – at least one carbon-carbon triple bond
• Aromatic Compounds (Benzene) – a six-membered unsaturated cyclic
hydrocarbon
• Alkyl halide/haloalkane – compounds in which a halogen atom replaces a
hydrogen atom of an alkane

• They can contain more than one type of halogen.

trichloromethane dichlorodifluoromethane
• Alcohol – compounds with a hydroxyl (-OH) group attached to an sp3-
hybridized carbon atom
• Ether – can be thought of as derivatives of water in which both H atoms have
been replaced by alkyl groups. Also named as alkoxyalkanes.

crown ethers
• Amine - may be considered as organic derivatives of ammonia
• Thiol - compounds with a sulfhydryl (-SH) group attached to an sp3-hybridized
carbon atom

• Thioether/sulfide – ether-like compound but with sulfur as the central atom

• Nitriles – carbon and nitrogen atom are sp-hybridized

• Aldehyde – carbonyl group is bonded to one H atom and one C atom (except
for formaldehyde)
• Ketone – carbonyl group bonded to 2 C atoms
• Carboxylic Acid – carbonyl group bonded to a hydroxyl group (carbonyl +
hydroxyl)

• Ester – carbonyl group bonded to an alkoxyl (-OR) group

• Amide – carbonyl group bonded to a nitrogen atom bearing H and/or alkyl
groups

• Acyl halide – carbonyl group bonded to a halogen atom

• Anhydride – carbonyl group bonded to another

carbonyl group through an oxygen atom
Identify all the functional groups present in the following organic compounds:

• Amide • Aromatic
• Aromatic • Alkane
• Ether • Ester
• Alkane • Amine
• Alcohol • Amide
• Amine • Carboxylic acid
• Early 18th century: organic compounds
named at the whim of their discoverers
Formic acid Urea
• 1892: 34 European chemists met in
Switzerland and developed the Geneva rules
Morphine
• Group became known as the International
Union of Pure and Applied Chemistry (IUPAC) Barbituric acid

• Geneva rules became known as the IUPAC

nomenclature
• System for naming compounds
• Based on functional groups
• IUPAC sets standards
• Why set standards?
• To avoid confusion
• To ensure that all compounds are given proper names

dimethyl ether ethanol

• Contains all single C-H bonds
• Saturated – all carbon atoms hold the highest allowed amount of hydrogen
atoms
• CnH2n+2
Saturated hydrocarbons

1. Choose longest chain / parent

chain

2. Between two chains of equal

length: choose parent chain with
higher number of substituents
3. Name the parent
chain

• Suffix –ane

• Prefix cyclo– for

ring structures
Name and identify parent chain

nonane heptane cycloheptane

4. Name substituents

• Same
terminologies as
naming the parent
chain
• Suffix –yl (alkyl
groups)
• Complex
substituents: treat
as mini-parent Parent: butyl
Subs: 2-methyl
chain 2 – locant / C atom no.
2-methylbutyl group
Common alkyl substituents
Indicate the systematic name and common name of all substituents:

1-methylethyl 1-methylethyl 2-methylpropyl

(isopropyl) (isopropyl) (isobutyl)

1-methylpropyl
(sec-butyl)
5. Assign locants to
substituents
• Assign lowest
possible locant
• 1st subs at lowest
possible locant
• If there is a tie, 2nd
subs at lowest
possible locant (and
so on…)
• If previous rule does
not break the tie,
assign lowest locant
alphabetically
6. Use prefixes for common substituents

Di = 2
Tri = 3
Tetra = 4
Penta = 5 and so on…
1,1,3-trimethylcyclohexane
7. Arrange substituents alphabetically &
indicate locants

Ignore prefixes except iso– and cyclo–

Punctuation rules

• Dash – separate number & letter

• Comma – separate number & number

• Parentheses – separate complex substituents

• Italicization – sec-, tert- BUT NOT iso-, neo-

1. Choose longest chain / parent chain
2. Between two chains of equal length: choose parent chain with higher
number of substituents
3. Name parent chain
4. Name substituents
5. Assign locants to substituents
6. Use prefixes for common substituents
7. Arrange substituents alphabetically & indicate locants
2,3,5,8-tetramethyldecane 4-(tert-butyl)-2,2-dimethylheptane
4-ethyl-5-isopropyl-2,2,7-trimethyloctane
 Give systematic names:

Parent: nonane 3-ethyl-2-methylhexane

Subs: 2-methyl
Parent: heptane Parent: Parent: hexane
3-ethyl
Subs: 2-methyl cyclopentane Subs: 3-ethyl
4-ethyl
3-methyl Subs: cyclopropyl 2-methyl
7-methyl
4-propyl
5-methyl
• Contains at least one C=C double bond
• Unsaturated – carbon atoms do not hold the highest allowed amount of
hydrogen atoms
• CnH2n
Unsaturated hydrocarbons
1. Choose parent chain with double bond or with greatest number of double
bonds
• Suffix –ene
• Indicate locant of double bond. If double bond is at C1, no need to indicate
locant. Otherwise, always indicate locant!

Butene 2-butene OR Penta-1,3-diene OR

but-2-ene 1,3-pentadiene
2. Assign lowest possible locant to the double bond despite the presence of
substituents
3. Alkene as substituent

Suffix –enyl

Parent: hexa-1,4-diene OR 1,4-hexadiene

Subs: 4,5-dimethyl
3-ethenyl

Name: 3-ethenyl-4,5-dimethylhexa-1,4-diene
OR 3-ethenyl-4,5-dimethyl-1,4-hexadiene
• Contains at least one C≡C bonds
• Unsaturated just like alkenes
• CnH2n-2
• Same rules as nomenclature of alkenes

• Parent name: suffix –yne

• Substituent name: suffix –ynyl

Parent: oct-1-yne OR 1-octyne

Subs: 4-methyl
5-(tert-butyl)

Name: 5-(tert-butyl)-4-methyloct-1-yne OR
5-(tert-butyl)-4-methyl-1-octyne
• Give the systematic name of the following organic compounds:

2,3-dimethylhexa-2,4-diene 4-Ethyl-3-isopropyl-2,5-
4-Ethyl-5-methyl-3-
OR dimethyl-2-heptane OR
propylheptyne
2,3-dimethyl-2,4-hexadiene 4-Ethyl-2,5-dimethyl-3-(1-
methylethyl)-2-heptane