CHAPTER 10 – ORGANIC CHEMISTRY
In 18th century classified compounds as organic &
inorganic. (organic – produced by living organisms, could
not synthesize from inorganic compounds; inorganic –
rocks, minerals)
Wohler (1828): synthesized an organic compound from 2
inorganic compounds:
NH4Cl
+
AgNCO
NH2CONH2 +
Urea
(found in urine)
AgCl
Organic Chemistry - study of compounds containing
carbon.
What are 4 most abundant elements necessary for life?
Organic compounds occur naturally or are prepared
synthetically
Inorganic Chemistry - study of compounds not containing
carbon.
More than 10,000,000 known organic compounds, only
about 1,700,000 inorganic compounds known.
Structures of Organic Compounds
Molecular Formula: Shows how many of each atom is
present, i.e. C2H6O
Structural Formula: Shows number of atoms plus the bonds
between atoms (how the atoms are attached to each other).
H
H
H–C–C–O–H
H
H
H
H
H–C–O–C–H
H
Ethanol
Dimethyl ether
H
Properties of a compound depend on its structure and not
molecular formula.
To Draw Organic Structures:
Carbon combines primarily w/ H, O, N, S, and halogens.
Each atom forms a specific number of covalent bonds.
SYMBOL
H
C
N
O
S
F, Cl, Br, I
# OF BONDS
1
4
3
2
2
1
ELEMENT NAME
Hydrogen
Carbon
Nitrogen
Oxygen
Sulfur
Fluorine, Chlorine,
Bromine, Iodine
HONC
Draw the structural formula for:
CH4
C2H6
C2H5Cl
CH4O
Why atoms form a specific # of bonds?
Review: Lewis Dot Structures
Octet Rule – 8 electrons in outer shell, except H
H
O
C2H5Cl
CH5N
N
C
Double and Triple Bonds
C= C
C= N–
C= O
–C=C–
–C=N
C= S
Draw the structural formula for:
C2H4
C2H2
HCN
H2CO
Functional Groups – an atom or group of atoms within a
molecule that cause the molecule to function in a specific
manner.
Funct. Groups are used to classify and name organic
compounds.
1) Alcohols
functional group: –OH (hydroxyl group) bonded to a
carbon having 4 single bonds
H
H
H–C – C– O – H
H
Ethanol
H
Molecular Formula: _____ C2H6O _______________
Condensed Structural Formula: shows structure/function of
compound, without drawing all the bonds
CH3CH2CH-
carbon bonded to 3 hydrogens
carbon bonded to 2 hydrogens
carbon bonded to 1 hydrogen
i.e. Ethanol:
CH3CH2OH
Write the condensed structural formula for: ____________
H
H
H
H
H
H
H
H
H–C – C– C – C – C – C – C– C–H
H
H
H
H
H
H
H
H
Three classes of Alcohols:
Primary (1o) Alcohol
Carbon bonded to -OH group is bonded to only one other C
i.e.
H
H
H–C–C–O–H
H
H
Secondary (2o) Alcohol
Carbon bonded to -OH group is bonded to 2 other carbons
i.e.
H
H
H–C–C–O–H
Condensed Struct Form: __________
H
CH3
Tertiary (3o) Alcohol
Carbon bonded to -OH group is bonded to 3 other carbons
i.e. H
CH3
H–C–C–O–H
H
CH3
Is this a primary, secondary or tertiary alcohol?
H
H
O H
H–C–C–C–H
H
2)
H H
Amines
functional group: –NH2 (amino group) bonded to one,
two or three carbons
Three classes of Amines:
Primary (1o) Amine
Nitrogen bonded to 1 carbon & 2 hydrogens
i.e.
H
H–C–N–H
H
H
Secondary (2o) Amine
Nitrogen bonded to 2 carbons & 1 hydrogen
i.e.
H
H–C–N–H
H
CH3
Tertiary (3o) Amine
Nitrogen bonded to 3 carbons
i.e.
CH3
CH3 – N
CH3
Is this a primary, secondary or tertiary amine?
CH3
CH3 – C – N – H
H H
Carbonyl group: C=O
3) Aldehyde: carbon of the carbonyl bonded to a hydrogen
i.e.
O
H – C – CH3
4) Ketone: carbon of carbonyl group bonded to 2 other
carbons
i.e.
O
H3C – C – CH3
5) Carboxylic Acids (-COOH carboxyl group): carbon of
carbonyl group bonded to a hydroxyl (OH) group
i.e.
O
CH3 – C – O - H
6) Carboxylic Esters: carbon of carbonyl group bonded to
an oxygen which is bonded to another C
i.e.
CH3 – C – O – CH3
O
Identify functional groups in these compounds:
O
O
CH3 – C – CH2 – CH2 – C – OH
O
CH3 – CH – C – OH
NH2
H
O
O
CH3 – CH – CH2 – CH2 – C – O - C H3