10 Chapter 10 10 Organic Chemistry

• Organic chemistry: the study of the compounds

of carbon.
• Organic compounds are made up of carbon and only a
few other elements.
• chief among these are hydrogen, oxygen, and nitrogen
Organic Chemistry • also present are sulfur, phosphorus, and halogens
(fluorine, chlorine, bromine, or iodine)

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10 Organic Chemistry 10 Organic Chemistry

• Why is organic chemistry a separate discipline • The sheer number of organic compounds
within chemistry? • Chemists have discovered or made over 10 million
• Historical: scientists at one time believed that a organic compounds and an estimated 100,000 new
ones are discovered or made each year.
“vital force” present in living organisms was
• By comparison, chemists have discovered or made an
necessary to produce an organic compound.
estimated 1.7 million inorganic compounds.
• The experiment of Wöhler in 1828 was the first in a
• Thus, approximately 85% of all known compounds are
series of experiments that led to the demise of the vital
organic.
force theory.
O • The link to biochemistry
heat
NH4 Cl + AgNCO H2 N-C-NH2 + AgCl
A mmonium Silver U rea Silver
• Carbohydrates, lipids, proteins, enzymes, nucleic
ch loride cyan ate chloride acids, hormones, vitamins, and almost all other
chemicals in living systems are organic compounds.
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1
10 Organic Chemistry 10 Organic Structure
• a comparison of organic and inorganic compounds • Structural formula: shows the atoms present in a
Organi c Comp ound s Ino rg an ic Co mpou nds molecule as well as the bonds that connect them.
Bond ing is almost entirel y co val ent M ost have i oni c bo nds • VSEPR model: the most common bond angles are
May be g ases, li quid s, o r so li ds M ost are sol id s w ith h ig h 109.5°, 120°, and 180°.
w ith l ow melti ng po ints (l ess melting po in ts HH H H HH

: :
than 360°C) H-C-C-H C C H-C C-H H-C-C-Cl :
Mo st are i nsol ubl e in w ater M any are so lu ble i n w ater HH H H HH
Eth ane Eth ylen e Acetylene Ch loroeth ane
Mo st are so lu ble i n o rg an ic so lv en ts A lmo st al l are i nso lubl e in (bond angles (bond angles (bond an gles (bond angles
such as d iethy l ether, to luene, and o rgani c so lvents 109.5°) 120°) 180°) 109.5°)
dichl orometh ane
H H H H
Aqu eo us so lutio ns do n ot A queous sol uti ons cond uct

:
: :

: :

:
condu ct el ectrici ty electrici ty H-C-O-H C O H-C-N-H C N
Al most all burn V ery f ew burn H H HH H H
Methanol Formald ehyde Methan amin e Methyleneimine
Reacti ons are usuall y sl ow Reactio ns are o ften very fast (b ond angles (bond angles (bond angles (bond angles 120°)
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10 Organic Structure 10 Functional Groups

• Among neutral (uncharged) organic compounds: • Functional group: an atom or group of atoms
• Carbon: normally forms four covalent bonds and has within a molecule that shows a characteristic set
no unshared pairs of electrons. of predictable physical and chemical properties.
• Hydrogen: forms one covalent bond and no unshared • Functional groups are important because
pairs of electrons.
• They undergo the same types of chemical reactions no
• Nitrogen: normally forms three covalent bonds and has matter in which molecule they are found.
one unshared pair of electrons.
• To a large measure they determine the chemical and
• Oxygen: normally forms two covalent bonds and has physical properties of a molecule.
two unshared pairs of electrons.
• They are the units by which we divide organic
• Halogen: normally forms one covalent bond and has compounds into families.
three unshared pairs of electrons.
• They provide the basis on which we derive names for
organic compounds.
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10 Functional Groups 10 Alcohols
• Six common functional groups • Alcohol: contains an OH (hydroxyl) group bonded
Functional to a tetrahedral carbon atom. For example,
Family group Example Name
Alcohol - OH CH3 CH2 OH Ethanol
ethanol:
R HH
Amine - NH2 CH3 CH2 NH 2 Ethanamine

:
R-C-O-H H-C-C-O-H CH3 CH2 OH
O O

:
Aldehyde - C- H CH3 CH Ethanal R HH
O O Function al group S tructural Cond ensed
Ketone - C- CH3 CCH3 Acetone (R = H or carbon formula stru ctural
O O goup formu la
Carboxylic acid - C- OH CH3 COH Acetic acid
• may be primary (1°), secondary (2°), or tertiary (3°)
O O H CH3
H
Carboxylic ester - C- OR CH3 COCH 2 CH 3 Ethyl acetate
CH3 -C-OH CH3 -C-OH CH3 -C-OH
H CH3 CH3
A 1° alcohol A 2° alcohol A 3° alcoh ol
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10 Alcohols 10 Alcohols
• Problem: draw Lewis structures and condensed • Problem: draw Lewis structures and condensed
structural formulas for the two alcohols with the structural formulas for the two alcohols with the
molecular formula C3H8O. molecular formula C3H8O.
• Solution:
Cond ensed stru ctural
Lew is stuctu res formulas
HH H
: :

H-C-C-C-O-H CH3 CH2 CH2 OH

HH H A p rimary alcohol

H
H:O: H OH
H C-C-C-H CH3 CHCH3
HH H A secon dary alcohol
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3
10 Amines 10 Amines
• Amine: a compound containing an amino group. • Problem: draw condensed structural formulas for the
• the amino group may be primary (1°), secondary (2°), or two primary amines with the molecular formula C3H9N.
tertiary (3°).

CH3 NH2 CH3 NH or (CH3 ) 2 NH CH3 NCH3 or (CH3 ) 3 N

CH3 CH3
Methylamin e D imethylamin e Trimethylamin e
(a 1° amine) (a 2° amine) (a 3° amine)

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10-14 10-15

10 Amines 10 Aldehydes and Ketones

• Problem: draw condensed structural formulas for the
two primary amines with the molecular formula C3H9N.
• Solution:
• Both contain a C=O (carbonyl) group.
• Aldehyde: contains a carbonyl group bonded to a
hydrogen; in formaldehyde, the simplest aldehyde, the
carbonyl group is bonded to two hydrogens.
• Ketone: contains a carbonyl group bonded to two
carbon atoms.

NH2 NH2 RO O RO R O
C-C-C-NH2 C-C-C CH3 CH2 CH2 NH2 CH3 CHCH3 R C-C-H CH3 CH R C-C-C R CH3 CCH3
Th e three carbon s may Add s even hydrogens to give each R R R
be bond ed to n itrogen carbon four b on ds an d give the Fun ctional A cetaldeh yde Functional Acetone
in tw o w ays correct molecu lar formula grou p (an aldehyde) group (a ketone)

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4
10 Aldehydes and Ketones 10 Aldehydes and Ketones
• Problem: draw condensed structural formulas for the • Problem: draw condensed structural formulas for the
two aldehydes with the molecular formula C4H8O. two aldehydes with the molecular formula C4H8O.
• Solution:
• First draw the functional group of an aldehyde and add
the remaining three carbons; these may be bonded in
two ways.
• Then add the seven hydrogens necessary to complete
the four bonds of each carbon.
O
O
CH3 CHCH
CH3 CH2 CH2 CH
CH3
or or

CH3 CH2 CH2 CHO CH3 CHCHO

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10-18 10-19

10 Carboxylic Acids 10 Carboxylic Acids

• Carboxylic acid: a compound containing a -COOH
(carboxyl: carbonyl + hydroxyl) group.
• In a condensed structural formula, a carboxyl group
may also be written -CO2H.
• Problem: draw a condensed structural formula for the
single carboxylic acid with the molecular formula
C3H6O2

O O
RCOH CH3 COH
Fu nctional Acetic acid
group (a carb oxylic acid )

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5
10 Carboxylic Acids 10 Functional Groups
• Problem: draw a condensed structural formula for the • Carboxylic ester: a derivative of a carboxylic acid
single carboxylic acid with the molecular formula in which the H of the carboxyl group is replaced
C3H6O2
by a carbon group.
• Solution: the only way the carbon atoms can be written
is three in a chain; the -COOH group must be on an end
carbon of the chain.

O O
O
C-O–C CH3 -C- O-CH3 or CH3 COOCH3 or CH3 CO 2 CH 3
CH3 CH2 COH or CH3 CH2 COOH
Functional Methyl acetate
group (an ester)

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10-22 10-23

10 Chapter 10 Organic Chemistry

End
Chapter 10

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