Professional Documents
Culture Documents
Organic Compounds,
Polymers,and Biochemicals
Index
22.1. Organic chemistry is the study of carbon compounds
22.2. Hydrocarbons consist of only C and H atoms
22.3. Ethers and alcohols are organic derivatives of water
22.4. Amines are organic derivatives of ammonia
22.5. Organic compounds with carbonyl groups include aldehy
des, ketones, and carboxylic acids
22.6. Polymers are composed of many repeating molecular
units
22.7. Most biochemicals are organic compounds
22.8. Nucleic acids carry our genetic information
Carbon Compounds
Carbon containing compounds exist in large
variety, mostly due to the multiple ways in which
C can form bonds
Some groups of atoms with similar bonding are
commonly seen, called functional groups.
Molecules may contain more than one functional
group
Can form chiral compounds
VSEPR Structures
Show all atoms
Show attachments between atoms but not how many
pairs of electrons were used
Show the geometric arrangement of the atoms
H H H
H H
H
C
C
H
H H
Condensed Structures
show the general arrangement of the atoms and the
number of atoms
no effort is made to indicate geometry, types of bonds,
or lone pairs
CH3CH2CH2CH2CH3
RC H
R C R'
R C OH
aldehyde
ketone
carboxylic acid
||
||
O
||
10
11
12
13
14
Your Turn!
Which of the following
contains an amide
group?
A. The top structure
B. The middle
structure
C. The bottom
structure
D. None of these
15
H H H H H
H C C C C C H
H H H H H
22.2. Hydrocarbons consist of only C and H atoms
16
Stick Figures
Each vertex and terminus is a carbon
Assumes that the termini contain as many H as
needed for saturation of the C
(hydrogens attached to hetero-atoms are shown)
H H H H
22.2. Hydrocarbons consist of only C and H atoms
17
Learning Check
Fill in the missing atoms and derive the condensed
structure
O
O
C5H12
22.2. Hydrocarbons consist of only C and H atoms
C4H8O2
18
Your Turn!
Which is the correct formula for the structure
shown?
A. C42H12
B. C24H12
C. C36G12
D. None of these
19
20
Alkanes (CnH2n+2)
Composed of hydrocarbon chains in which carbons
are attached to one another by single bonds
Are named by the number of C in the chain and
where any substitutions are found
Prefixes and the associated numbers of carbon
atoms
meth-1
eth-2
prop-3
but-4
pent-5
hex-6
hept-7
oct-8
non-9
dec-10
21
Naming Alkanes
1. Find the longest continuous chain of carbons-the root.
22
Naming (Cont.)
4. Number root from side closest to the first
branch
5. Use numbers to tell where the side chains
sprout from the root
6. Put a dash between any number and letter or
any letter and number. Use a comma between
two numbers
7. Use the prefix cyclo for ring systems
23
3-ethyl-2-methylhexane
2,3,3,4-tetramethylhexane
3-methylheptane
3-ethyl-4-methylhexane
24
Your Turn!
Name the structure shown:
A. 1,2-dimethylpentane
B. 3-methylhexane
C. 2-ethylpentane
D. None of these
25
Reactions Of Alkanes
Alkanes are generally stable at room temperature
They burn in air to given carbon dioxide
When heated at high temperature they crack (break into
smaller molecules)
CH 4 high
tempe rature
C 2H 2
CH 3CH 3 high
tempe rature
H 2 C CH 2 H 2
ethane
ethene
26
Unsaturated Hydrocarbons
Hydrocarbons with one or more double bonds are
members of the alkene family
open chain alkenes have the general formula C2H2n
27
Naming Alkenes
The parent chain must include the double bond
The parent alkene chain must be numbered from
whichever end gives the first carbon of the double
bond the lowest number
This number, followed by a hyphen, precedes the
name of the parent chain, unless there is no
ambiguity about where the double bond occurs
The locations of branches are not a factor in
numbering the chain
Alkyl groups are named and located as before
22.2. Hydrocarbons consist of only C and H atoms
28
ethylene
2,3-dimethyl-1-pentene
29
Your Turn!
Which name is not correct?
A.
3-pentene
B.
2-pentene
C.
2-methyl-1-butene
30
Geometric Isomers
Cis and trans isomers exist when there
is a plane of a double bond or of a
ring structure
cis same
trans-opposite
31
Your Turn
Which isomer is shown:
A. cisB. transC. cant tell
32
33
Aromatic Compounds
Contain a benzene(C6H5-) ring with delocalized
electrons
Aromatic compounds undergo substitution reactions
instead of addition reactions because of the
resonance energy of the ring
example: C6H6 + Cl2C6H5Cl + HCl
34
Ethers (ROR)
Result when both hydrogen atoms in water are
replaced with alkyl groups
Are almost as chemically inert as alkanes: they
burn and are split apart when boiled in
concentrated acid
Are named by naming each alkyl group,
alphabetically, and end with ether
Learning Check:
CH3OCH3
CH3CH2OCH3
CH3CH2OCH2CH3
dimethyl ether
ethyl methyl ether
diethyl ether
35
Alcohols (ROH)
When an alkyl group replaces a hydrogen in water, an
alcohol results
The name ending for alcohols is ol
The parent chain must include the carbon containing the
OH group
Learning Check: Name the following
CH3CH2OH
CH3CH2CH2CH2OH
ethanol
butanol
36
Oxidation of Alcohols
If the alcohol carbon atom holds at least one H atom, it
can be replaced with bonds to oxygen
O
RCH 2OH
alcohol
Further
oxidation
||
R CH
oxidation
aldehyde
O
||
||
R C OH
carboxylic acid
Further
oxidation
O
||
CH 3 C OH
37
Dehydration Of Alcohols:
The reverse the the addition of water to an
alkene, it is an example of an elimination
reaction
CH 3 C H C H 2 CH 3CH CH 2 H 2O
|
OH
38
1 - bromopropane
39
Your Turn!
What type of structure is shown
A. Alcohol
B. Ether
C. Peroxide
D. aldehyde
40
Amines
Are derivatives of ammonia where one or more
hydrogens have been replaced with alkyl groups
NH3 is ammonia
CH3NH2 is methylamine
(CH3)2NH is dimethylamine and (CH3)3N is
trimethylamine (bp 3oC).
41
Protonated Amines
Are more soluble in water than amines
Protonated amines (like protonated ammonia) are weak
acids that can react with base
NH 4 (aq) OH (aq) NH 3 (aq) H 2O
CH 3CH 2 NH 3 (aq) OH (aq) CH 3CH 2 NH 2 (aq) H 2O
42
Aldehydes
The IUPAC name ending for an aldehyde is al
The parent chain is the longest chain that includes
the aldehyde group
Ketones
The IUPAC ending for ketones is one.
The parent chain must include the
carbonyl group
propanone 3-pentanone
1 - propanol
OH
|
CH 3 C CH 3 H 2 CH 3 C H CH 3
2 - propanol
Carboxylic Acids
The IUPAC name ending for carboxylic acids is
oic acid. the parent chain must include the
carbonyl carbon, which is numbered as position 1
Your Turn!
Which of the following contain a carbonyl group?
A. amine
B. amide
C. carboxylic acid
D. All contain a carbonyl
Esters
In esters, the OH of the carboxyl group is
replaced by -OR
Name the alkyl group attached to the O atom
followed by a separate word generated from
the name of the parent acid by changing oic
acid to -ate
methyl methanoate
ethyl ethanoate
Preparation Of Esters
Esters can be prepared by heating the parent acid with
an alcohol in the presence of an acid catalyst
O
||
||
R C OH HOR' R C OR' H 2O
O
||
||
ethanol
ethyl ethanoate
Reactions of Esters
Carboxylic acids and alcohols can be obtained by
heating esters with acid in a large excess of water
Esters are split apart by the action of base in a reaction
called saponification
O
||
heat
ethyl ethanoate
O
||
ethanol
Amides (RCONH2)
Carboxylic acids can also be converted into amides, a
functional group found in proteins
Simple amides are those in which the nitrogen bears
no alkyl groups, only hydrogen atoms
The IUPAC names of simple amides are generated by
replacing the oic acid of the parent carboxylic acid
with -amide
H2N
O
NH2
propanamide
2-methyl-butanamide
Preparation of Amides
One way to prepare simple amides is by heating
a carboxylic acid in excess ammonia
O
||
R C OH NH 3
heat
||
R C NH 2 H 2O
O
||
CH 3CH 2 C OH NH 3
propanoic acid
heat
||
CH 3CH 2 C NH 2 H 2O
propanamide
Reactions of Amides
Amides, like esters, can be hydrolyzed
O
||
R C NH 2 H 2O
heat
||
R C OH NH 3
O
||
CH 3CH 2 C NH 2 H 2O
propanamide
heat
||
CH 3CH 2 C OH NH 3
propanoic acid
Your Turn!
Which of these can be hydrolyzed (react with water)
A. amides
B. alkanes
C. alcohols
D. None of these
Polymers
Are large molecules with repeating units called
monomers
55
56
57
58
Crosslinking
Branches on polymers
make them susceptible
to interaction with other
polymers
Increased crosslinking
leads to increased
strength
The concept behind
vulcanized rubber
59
60
61
Your Turn!
One form of Gak can be made by combining
dissolved white glue and dissolved borax
powder. What characteristics would you expect
if the amount of cross-linker (the borax) is
increased in the blend?
A. It becomes more viscous
B. It becomes more solid
C. It tears rather than stretches
D. All of the above
62
Biochemistry
The systematic study of the chemicals of living things
A variety of compounds are required for cells to work:
lipids
carbohydrates
proteins
nucleic acids
63
Carbohydrates
Are naturally occurring polyhydroxyaldehydes or
polyhydroxyketones, or else compounds that react
with water to give these
Types:
monosaccharides
disaccharides
polysaccharides
64
Monosaccharides
Are carbohydrates that do not react with water
The most common monosaccharide is glucose
(pentahydroxyaldehyde)
glucose is the chief carbohydrate in blood, and provides
a building units for polysaccharides like cellulose and
starch
OH
OH
OH
H2C H C H C
C H C H CH
OH OH O
H2
HO
C OH
HC CH
HO CH
O
HC CH
OH
HO
-glucose
65
Disaccharides
Are carbohydrates that split into two
monosaccharide molecules by reacting with water
example: sucrose (table sugar, cane sugar, or beet
sugar) which gives glucose and fructose upon
hydrolysis
66
Polysaccharides
Are naturally occurring polymers whose molecules
involve thousands of monosaccharide units linked to
each other by oxygen bridges
include starch, glycogen, and cellulose -all give only
glucose upon hydrolysis
plants store energy as starch
the hydrolysis of amylose (the simplest starch) can be
represented as:
Glu (O Glu ) n OH nH 2O n glucose
amylose (n is large)
22.7. Most biochemicals are organic compounds
67
Storage of glucose
Animals store glucose for energy as glycogen
excess glucose is converted to glycogen by liver and
muscle cells and stored for later use
68
Lipids
Are fats and oils that are non-polar, so they do not
dissolve in water
Are amphipathic:
the purely hydrocarbon-like portions (the long R groups
contributed by the fatty acids) avoid water and are
called hydrophobic or water fearing
the polar heads are hydrophilic or water loving
69
Triacylglycerols
Are esters between glycerol and include
edible fats and oils like olive oil, butterfat,
and lard
Are called vegetable oils when derived
from plants and animal fats when derived
from animals, and are made from fatty
acids
Are said to be polyunsaturated; vegetable
oils tend to have more alkene double
bonds per molecule than animal fats
22.7. Most biochemicals are organic compounds
70
Glycerophospholipids
The lipids involved in animal cell membrane are called
glycerophospholipids
71
Your Turn!
Which are forms of fats?
A. Lipids
B. Glycerols
C. Polysaccharides
D. All of these
72
Proteins
The dominant structural units of proteins are
macromolecules called polypeptides
polypeptides are made from a set of about 20
monomers called amino acids
polypeptides are copolymers of the amino acids
73
Reactions of Proteins
The final shape of a protein, called its native
form, is critical to its ability to function
Physical agents such as heat, poisons, and certain
solvents can alter a proteins native form
when this happened the protein is said to have been
denatured
74
Nucleic Acids
Carry the genetic
code
Are made of amino
acids
75
Reactions of DNA
The best hydrogen bonds are formed when the base
pairs that makeup the backbone match
Adenine (A) pairs with thymine (T), cytosine (C) pairs with
guanine (G), etc
76
Replication of DNA
77
DNA Characteristics
A single human gene has between 1000 and
3000 bases
the bases do not occur continuously on a DNA
molecule
the separated segments of a DNA chain that make up
a gene are called exons because that unit helps to
express a message
the sections of DNA between the exons are called
introns because they are units that interrupt the gene
78
Preparation of Polypeptides
Each polypeptide in a cell is made under the direction
of its own gene
The production of a polypeptide can be represented as:
DNA transcript
ion RNA translatio
n polypeptide
79
RNA
Four types of RNA are involved in the connection of
the gene to the polypeptide
ribosomal RNA or rRNA is packed together with enzymes
in ribosomes, the manufacturing stations for polypeptides.
messenger RNA or mRNA brings the blueprints for
particular polypeptide to the manufacturing station
(ribosome)
heterogeneous nuclear RNA or hnRNA carries the
prefabricated parts (amino acids) to the ribosome
transfer RNA or t-RNA carries amino acids to the
ribosomes
80
Genetic Defects
About 2000 diseases are attributed to various
kinds of defects in the genetic machinery of
cells
if a single base is wrong in a gene, it could result in
a completely different polypeptide being produced,
possibly with fatal consequences
81
Viruses
Viruses are packages of chemicals usually
consisting of nucleic acid and protein
Their nucleic acid takes over the genetic
machinery in certain cells of the host tissues
causing them to manufacture more virus particles
The host cell bursts, releasing the newly
manufactured viruses, which can infect more cells
82
Your Turn!
How many types of RNA are there in a living
organism?
A. 1
B. 2
C. 3
D. 4
83
Your Turn!
How many types of DNA are there in a living
organism?
A. 1
B. 2
C. 3
D. 4
84