Introduction to Organic

Chemistry

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 The Nature of Organic Molecules
► Organic chemistry: The study of carbon compounds.
► Carbon ALWAYS forms four bonds.

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► Carbon’s 4 bonds can be any combination of single,
double and triple bonds

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PROPERTIES OF ORGANIC COMPOUNDS

 Nonelectrolytes (do not conduct electricity)

 React slowly because they are covalent
(nonmetal + nonmetal)
 Usually low melting point and boiling point
 Insoluble and immiscible in water
 Drawing Organic Structures

Condensed structure: A shorthand way of drawing

structures in which C-C and C-H bonds are
understood rather than shown.

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 Drawing Organic Structures
Line structure: An even shorter notation:

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 Families of Organic Molecules:
Functional Groups
► Organic compounds are put into families
(categories) according to
►The types of atoms attached to the carbons
►The types of bonds between the carbons
►Single, double, triple

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8
 Organic Nomenclature
► Basic naming system (nomenclature):

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 Hydrocarbon Nomenclature
► The simplest group of Families are the hydrocarbons…
compounds containing only carbon and hydrogen
►All carbon-carbon single bonds: alkanes
►At least one C=C double bond: alkenes
►At least one C  C triple bond: alkynes

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 Hydrocarbon Nomenclature
► Hydrocarbons can be
►“straight” chain

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 Hydrocarbon Nomenclature
► Hydrocarbons can be
►“straight” chain

► branched chain

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 Hydrocarbon Nomenclature
► Hydrocarbons can be
►“straight” chain

► branched chain

► cyclic

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 Naming Alkanes
► Suffix: -ane
► Parent : based on # of Carbons in longest,
continuous chain

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1 carbon meth-
2 carbons eth-
3 carbons prop-
4 carbons but-
5 carbons pent-
6 carbons hex-
7 carbons hept-
8 carbons oct-
9 carbons non-
10 carbons dec-

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 Naming Alkanes
►Examples of “Straight chain” alkanes:
CH3CH2CH3

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► What is the chemical
formula of this
molecule?

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 Naming Branched-Chain Alkanes
► Branched-chain alkanes have “substituents” branching off of the main
chain.
► For hydrocarbons, these substituents (or “branches”) are also hydrocarbons
►# of carbons in branch: normal prefix
►Suffix of hydrocarbon branch: -yl
►Name must include WHICH carbon of the main chain the branch is
connected to.

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 12.6 Naming Branched Alkanes
► STEP 1: Name the main chain (parent + suffix). Find the longest
continuous chain of carbons!
► STEP 2: Number the carbon atoms in the main chain. Begin at the end
nearer the first branch point
► STEP 3: Identify the branching substituents, and number each
according to its point of attachment to the main chain
► STEP 4:Write the name as a single word,
►If two or more identical substituents are present, use one of the prefixes
di-, tri-, tetra-
►If two or more different substituent groups are present, cite them in
alphabetical order

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20
Naming Cyclic Alkanes

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 Naming Cyclic Alkanes
► Naming rules are mostly the same as for other alkanes
► Additional Rules:
►The ring is ALWAYS the main chain
►The prefix “cyclo” is added to the name of the main
chain
►If only 1 branch, it doesn’t need to be numbered
►If more than one branch, number the carbons in the
ring to get the lowest combination of numbers of
branch locations.

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Alkenes and Alkynes

Chapter Seven
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Naming Alkenes and Alkynes

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Naming Alkenes and Alkynes

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 13.2 Naming Alkenes and Alkynes

► Very similar rules as for alkanes

► Additional rules:
►Choose longest chain that contains the
double or triple bond
►Suffix for alkenes: -ene
►Suffix for alkynes: -yne
►Include a number with the parent to
indicate which carbon the double/triple
bond starts on.
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►
3-methylcylclopentene

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► Cyclic alkene special rules
►Carbons 1 and 2 MUST go “through” the double bond
►If there is more than one double bond, number the ring to give the
double bonds the lowest numbers… then worry about branches.

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►5-ethyl-1,3-cylclohexene

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 Isomers

► 2 or more molecules with the same number of

each atom, but are connected differently.
► These molecules will have different names.

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Isomers

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Some Compounds With
Oxygen or a Halogen

Chapter Seven
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 Alcohols and Ethers
► An alcohol has an –OH covalently bonded to a carbon chain.

► These compounds are NOT basic.

► An ether has an O in the midst of a carbon chain.

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 Naming Alcohols

4-methyl-1-cyclohexanol methanol

1-propanol (only 3 carbons, not 4)

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 Naming Alcohols
► 1. Number the longest carbon chain starting at the end
that gets you to the OH the quickest.
► 2. Suffix: replace the “e” at the end of the normal name for
the main chain with “ol”
► 3. Denote location of the OH the same way you show the
location of a double or triple bond
► 4. Name and slow location of any hydrocarbon branches.

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 Properties of Alcohols
Properties:
•Polar due to the electronegative oxygen.
•Hydrogen bonding increases boiling point and
solubility in water.
•Small alcohols are liquids at room temperature, while
larger ones can be waxy solids.
•Boiling Point: Increases with molecular size (e.g.,
ethanol: 78°C).
•Melting Point: Lower for short-chain alcohols,
increases with size (e.g., ethanol: -114°C).
•State at Room Temp: Liquid (small alcohols); waxy
solid (long-chain alcohols). 36
 Ethers
Ethers are named by identifying the two carbon
“branches” attached to the oxygen atom (in alph.
order) and adding the word ether.

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 Ethers

Butyl propyl ether

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 Properties of Ethers
•Properties:
•Slightly polar, but cannot hydrogen bond, leading to
lower boiling points than alcohols.
•Highly volatile and flammable.
•Many are gases or low-boiling liquids.
•Boiling Point: Much lower than alcohols (e.g., diethyl
ether: 34.6°C).
•Melting Point: Low (e.g., dimethyl ether: -138.5°C).
•State at Room Temp: Mostly liquid, small ethers can be
gases.
•Commonly Found In: Anesthetics, solvents, fuel
additives 39
Halogen Containing Compounds

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 Halogen Containing Compounds
► Halogens: Fluorine, chlorine, bromine, iodine
►As a branch: fluoro, chloro, bromo, iodo
► Halogen branches are given “numbering preference” over
hydrocarbon branches
►But NOT over any substituent that determines the family
of the compound (like alcohols, double bonds, etc.)

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Aldehydes and Ketones

Chapter Seven
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 The C=O group
► Both aldehydes and ketones contain a C=O
group
► They are NOT alkenes… alkenes have C=C
bonds
► The difference between aldehydes and
ketones is the placement of the C=O group.

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 Aldehydes

CH3CHO

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 Aldehydes

Propanal
3-methylbutanal

CH3CHO
Ethanal
methanal
(common name: formaldehyde)
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 Aldehydes
►Aldehydes:
►The Carbon of the C=O group is one of the
end carbons
►Suffix: -al
►No need to show its number… it’s ALWAYS
“1” if it’s an aldehyde.

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 Properties of Aldehydes
•Properties:
•Polar due to the carbonyl group.
•Reactive; can oxidize to form carboxylic acids.
•Many have strong, pungent odors.
•Boiling Point: Higher than ethers but lower than
alcohols (e.g., formaldehyde gas: -19°C, acetaldehyde:
20°C).
•Melting Point: Varies (e.g., formaldehyde: -92°C).
•State at Room Temp: Small aldehydes = gases, larger
ones = liquids or solids.
•Commonly Found In: Preservatives (formaldehyde),
perfumes, flavoring agents (vanillin) 47
 Ketones
CH3COCH 2CH2CH3
(how can you know it’s not an ether??)

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 Ketones
2-butanone
4-methyl-3-hexanone
CH3COCH2CH2CH3
(how can you know it’s not an ether??)
2-pentanone

cyclohexanone

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 Ketones
►Ketones:
►The Carbon in the C=O group is one of the
INTERIOR carbons
►Suffix: -one
►Location of the =O must be numbered (except
for propanone and butanone)

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 Properties of Ketones

•Properties:
•Polar, but cannot hydrogen bond with itself.
•Soluble in water (small ketones), but solubility
decreases with size.
•Often liquid with pleasant odors.
•Boiling Point: Higher than ethers but lower than
alcohols (e.g., acetone: 56°C).
•Melting Point: Usually low (e.g., acetone: -95°C).
•State at Room Temp: Liquid.
•Commonly Found In: Nail polish remover (acetone),
hormones (testosterone), solvents
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Carboxylic Acids

Chapter Seven
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 Carboxylic Acids
► Carboxylic acids look like a combination of
an alcohol and an aldehyde … on the same
carbon.

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 Carboxylic Acids
methanoic acid
(common name: formic acid)

CH3CO2H
ethanoic acid
(common name: acetic acid)

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 Acidity of Carboxylic Acids
Carboxylic acids are weak acids

(ethanoic acid)

Carboxylic acids are weak acids because they

only partially ionize in solution. Their solutions
do not contain many hydrogen ions compared
to a solution of a strong acid at the same 55
 Carboxylic Acids
► Carboxylic acids
►Suffix: -oic acid
►No need to number the acid group… it has to be on an end carbon, so it is automatically “1-”

propanoic acid

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 Properties of Carboxylic Acids
•Properties:
•Highly polar, can form hydrogen bonds.
•Weak acids, donate H⁺ in solutions.
•Higher boiling points than alcohols due to dimer formation.
•Boiling Point: Very high due to strong hydrogen bonding (e.g.,
acetic acid: 118°C).
•Melting Point: Varies (e.g., acetic acid: 16°C, benzoic acid:
122°C).
•State at Room Temp: Small ones are liquids, larger ones are waxy
solids.
•Commonly Found In: Vinegar (acetic acid), citrus fruits (citric
acid), fatty acids in soaps.

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Ester

Chapter Seven
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 Ester
a) Contains COO
connecting parent chain to branch
a) Smell nice! Found in perfumes, foods
b) Has the suffix -oate
 Properties of Esters

•Properties:
•Pleasant fruity odor, found in perfumes and food
flavorings.
•Lower boiling points than alcohols and acids.
•Less polar, less soluble in water.
•Boiling Point: Lower than carboxylic acids (e.g., ethyl
acetate: 77°C).
•Melting Point: Varies (e.g., methyl formate: -99°C).
•State at Room Temp: Mostly liquids.
•Commonly Found In: Artificial flavors, perfumes, fats
& oils. 60
Amine

Chapter Seven
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Amine
a) Nitrogen is present
b)Used in dyes, found in
proteins, DNA
c) Has the suffix -amine
 Properties of Amine
•Properties:
•Basic due to lone pair on nitrogen.
•Fishy odor (especially in simple amines).
•Forms hydrogen bonds, increasing boiling points.
•Boiling Point: Lower than alcohols (e.g.,
methylamine: -6°C).
•Melting Point: Varies (e.g., aniline: -6°C).
•State at Room Temp: Small amines = gases;
larger ones = liquids or solids.
•Commonly Found In: Amino acids, proteins,
neurotransmitters.
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Amide

Chapter Seven
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 Amide
a) Contains
b) Used in dyes
c) Has the suffix -amide

propanamide
 Properties of Amide

•Properties:
•Neutral, not basic like amines.
•Strong hydrogen bonding leads to high boiling points.
•Very stable due to resonance.
•Boiling Point: Very high (e.g., acetamide: 221°C).
•Melting Point: Often high (e.g., acetamide: 82°C).
•State at Room Temp: Solids (except small amides, which
can be liquids).
•Commonly Found In: Proteins (peptide bonds), urea,
painkillers (acetamide).
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Aromatic Compound

Chapter Seven
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 Aromatic Hydrocarbons
a) 6 carbons are in a closed ring with alternating
double and single bonds
b) Called benzene

Methylbenzene 1,4-dichloro benzene

c) It is very stable
d) Can be substituted
 Thiols

•Structure: R-SH
•Properties:
•Weakly polar, but less than hydroxyl (-OH).
•Can form disulfide bonds (-S-S-), important for protein
structure.
•Strong, unpleasant odor (e.g., rotten eggs).
•Boiling Point: Low (e.g., methanethiol: 6°C).
•Melting Point: Low.
•State at Room Temp: Gases or liquids.
•Commonly Found In: Proteins (cysteine), garlic, skunk
spray.
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 Phosphate Groups

•Properties:
•Highly polar and negatively charged.
•Acidic, releases H⁺ ions.
•Plays a role in energy storage (ATP) and DNA
structure.
•Boiling Point: N/A (decomposes before boiling).
•Melting Point: Varies (e.g., phosphoric acid: 42°C).
•State at Room Temp: Solid or liquid.
•Commonly Found In: ATP (energy carrier), DNA,
detergents.
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 Nitriles
•Structure: R-C≡N
•Properties:
•Highly polar due to the triple bond.
•Water-soluble (small nitriles).
•Used in pharmaceuticals and synthetic fibers.
•Boiling Point: Higher than alkanes (e.g., acetonitrile:
82°C).
•Melting Point: Varies (e.g., acetonitrile: -46°C).
•State at Room Temp: Liquid.
•Commonly Found In: Plastics, drugs, cyanide-based
materials.
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 Nitro

•Structure: R-NO₂
•Properties:
•Strongly polar due to nitrogen-oxygen bonds.
•Often explosive in organic compounds.
•Boiling Point: High due to polarity (e.g., nitromethane:
101°C).
•Melting Point: Varies (e.g., nitrobenzene: 5°C).
•State at Room Temp: Mostly liquids.
•Commonly Found In: TNT (trinitrotoluene),
explosives, dyes, pharmaceuticals.
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 Imine

•Structure: R-C=NH or R-C=N-R'

•Properties:
•Intermediate in amino acid metabolism.
•Less polar than ketones and aldehydes.
•Boiling Point: Moderate (depends on R-groups).
•Melting Point: Varies.
•State at Room Temp: Liquids or solids.
•Commonly Found In: Schiff bases, enzyme
chemistry.

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