Organic Chemistry

6th Edition
Paula Yurkanis Bruice
Chapter 2
An Introduction to
Organic Compounds

Nomenclature,
Physical Properties,
and
Representation of
Structure
IGGIK
IHTILE
.… T.
-

le ,

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Alkanes are hydrocarbons containing only single bonds

General formula: CnH2n+2

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 …

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Constitutional isomers have the same molecular formula,
but their atoms are linked differently

neopentane
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 Nomenclature of Alkyl Substituents
Removing a hydrogen from an alkane results in an alkyl
substituent

…Oa )

-
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If a hydrogen is replaced by an OH, the compound

√
becomes an alcohol;

if it is replaced by an NH2, the compound becomes an amine;

θ
~ '

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if it is replaced by a halogen, the compound becomes an
alkyl halide;

and if it is replaced by an OR, the compound becomes an

ether
>
8

Some common names are derived from the alkyl groups

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 Different Kinds of Carbons and
Hydrogens

1
3
&

2 3

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A compound can have more than one name, but a
name must specify only one compound

The prefix “tert” is used for tert-butyl and tert-pentyl

compounds
ex 3

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The use of an “iso” prefix:

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 …

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 Nomenclature of Alkanes 30 ~ 40

1. Determine the number of carbons in the longest 4444

continuous
chain

&
∅

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2. Number the chain so that the substituent gets the lowest
number

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Numbers are used only for systematic names but not
common names

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3. Number the substituents to yield the lowest possible number
in the number of the compound

1 .
mono substituents are listed in
2 .
di alphabetical order
3 .
fri

4 fetra .

5 .
Penta

6 Hexa .

08880
4

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4. Assign the lowest possible numbers to all of the substituents

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5. If the same substituent numbers are obtained in both directions,
the first group cited receives the lower number

6. If a compound has two or more chains of the same length,

the
parent hydrocarbon is the chain with the greatest number of

X
substituents
od

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7. Certain common nomenclatures are used in the IUPAC system

Some substituents have only a systematic name

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 Systematic Naming of Substituents
Systematic Method
•Determine longest chain starting with the point of attachment.
•Name longest chain as “alkyl.”
•Number and name substituents and add to “alkyl” as prefix.
•Name the substituent as (#-alkylalkyl). The parentheses distinguish
substituent numbering from the numbering of the longest chain.

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 Nomenclature of Cycloalkanes
1. No number is needed for a single substituent on a ring

2. Name the two substituents in alphabetical order

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3. If there are more than two substituents, they are cited in
alphabetical order

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 Nomenclature of Alkyl Halides

In the IUPAC system, alkyl halides are named as substituted

alkanes
r
7?
of entine

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 Nomenclature of Ethers

As substituents:

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 Nomenclature of Alcohols
• In an alcohol, the OH is a functional group

• A functional group is the center of reactivity in a

molecule

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1. Determine the longest hydrocarbon containing the functional
group:

2. The functional group suffix should get the lowest number:

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3. When there is both a functional group suffix and a substituent,
the functional group suffix gets the lowest number:

4. The chain is numbered in the direction that gives a substituent

the lowest number:

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5. The functional group substituent on a ring gets the number 1,
but the functional group is not numbered in the name:

CH3 HO CH3 OH
CH3
CH3
OH
3-methylcyclohexanol 1-methylcyclohexanol 2, 2-dimethylcyclopentanol
not not not
3-methylcyclohexan-1-ol 1-methylcyclohexan-1-ol 2, 2-dimethylcyclopentan-1-ol

6. If there is more than one substituent, the substituents are cited

in alphabetical order:

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Nomenclature of Amines

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The substituents are listed in alphabetical order and a number or
an “N” is assigned to each one:

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Naming Quaternary Ammonium Salts

A disinfectant and Antiseptic

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 Common Names Preferred over
Systematic Names in Some Cases

Pentacyclo[4.2.0.02,5.03,8.04,7]oct
ane
“Cubane”

Nonacyclo[11.7.1.12,28.0 3,16.04,13.05,10.06,14.07,11.0 15,20]

docosane
“Bastardane” The unwanted alkane. 0
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 Structures of Alkyl Halides

↑ Ψ

√
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Structures of Alcohol and Ether

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Structures of Amines

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 Attractive Forces

van der Waals force

Dipole–dipole interaction

Hydrogen bonds

The greater the attractive forces between molecules,

the higher is the boiling point of the compound.

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 van der Waals Forces

The boiling point of a compound increases with the

increase in van der Waals force
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 Dipole–Dipole Interaction

Dipole–dipole interactions are stronger than van der

Waals force but weaker than ionic or covalent bonds

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Hydrogen bonds are stronger than other dipole-dipole
interactions and van der Waals force

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Both van der Waals and dipole-dipole interactions must
be overcome for an alkyl halide to boil

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The melting point is influenced by the packing of the
molecules in the crystal lattice

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 Like Dissolves Like
• Polar compound dissolves in polar solvent

• Nonpolar compound dissolves in nonpolar solvent

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“Like Dissolves Like” Concept Important in
Drug Action
• Crossing the Blood-Brain Barrier requires a fat-soluble drug.
• THC and Barbiturates possess hydrocarbon tails to facilitate
crossing this barrier.
• Hydrocarbon substituents are termed “lipophilic” or fat-loving.
• Substituents that possess hydrogen-bonding capability are
termed “hydrophilic”or water-loving.

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 Conformations of Alkanes:
Rotation about Carbon–Carbon Bonds

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Different Conformations of Ethane

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A staggered conformer is more stable than an eclipsed
conformer

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Conformations of n-Butane

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Steric strain: repulsion between the electron clouds of atoms or
groups
The gauche interaction destabilizes the gauche 0
conformation © 2011 Pearson Education, Inc.
 Cycloalkanes: Ring Strain
• Angle strain results when bond angles deviate from the
ideal 109.5° bond angle

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The chair conformation of cyclohexane is free of strain

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Ring Flipping in Cyclohexane

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Drawing Cyclohexane

'I
,

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The Conformations of Cyclohexane
and Their Energies

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Conformations of Monosubstituted
Cyclohexanes

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Steric Strain of 1,3-Diaxial Interaction in
Methylcyclohexane

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The larger the substituent on a cyclohexane ring, the
more the equatorial substituted conformer will be
favored

Keq = [equatorial conformer]/[axial conformer]

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The Chair Conformers of cis- or
trans-1,4-Dimethylcyclohexane

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 Systematic Method for Drawing Chair Conformations of Cis and Trans
Substituted Cyclohexanes

1. Label the chair conformer axial and equatorial bonds

with either up (U) or down (D) based on the flat
cyclohexane ring.

2. Consider Cis substituents as either UU or DD and Trans

substituents as either UD or DU.
3. Example, Draw the more stable conformation of cis-
1,3-dimethylcyclohexane:

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1-tert-Butyl-3-Methylcyclohexane

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Conformations and Drug Action
Etorphine, a rigid morphine analog:

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 Conformations and Drug Action
• Conformations of the neurotransmitter
dopamine

• Apomorphine natural products: conformationally-restricted

forms of dopamine:

•Apomorphine, active dopamine mimic; Isoapomorphine, inactive

as dopamine mimic 0
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