Ch10-Organic Compounds, Polymers, and Biochemicals

Ch 22.
Organic Compounds,
Polymers,and Biochemicals
Brady & Senese, 5th Ed.

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
aldehydes, 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
2
Organic Compounds Are Diverse
Carbon compounds are greatly variant due to the

properties of C:
C is able to bond multiply
C is able to catenate
C is able to bond with a wide variety of elements
Isomers are possible when there is a carbon chain
Combinations of functional groups give great diversity
Carbon can form rings
22.1. Organic chemistry is the study of carbon compounds 3

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 C
H C C H
H 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

Alcohols & Ethers Are Polar
Contain C, H, and O, all with single bonds.

Alcohols end in OH (R-OH)
Ethers have an O atom in the chain (R-O-R)

The Carbonyl Group
When C in a chain has a double bond to an oxygen, the
group is termed a carbonyl
Aldehydes, ketones, carboxylic acids, and amides all
contain carbonyl groups
O O O
|| || ||
RC H R C R' R C OH
aldehyde ketone carboxylicacid

Aldehydes & Ketones Are Polar
Each has a carbon chain terminating in a carbonyl.

Aldehydes then have an added H (RCOH)
Ketones have another carbon chain (RCOR)

Amines & Amides Are Polar
Amines contain -NH2 on carbon chain (RNHR)

Amides contain NH2 on carbon chain with
carbonyl (RCONH2)

Carboxylic Acids & Esters Are Polar
Both have a carbon chain terminating in a

carbonyl
Carboxylic acids then have an OH group
A combined carbonyl and hydroxyl group form a
carboxyl group (RCOOH)
Esters then have a singly bound O, then another
carbon chain (RCOOR)

Identify The Functional Groups Present

Using Functional Groups
Collecting molecules into families means that only

a few kinds of reactions must be learned
The emphasis is on the properties of the functional
group, not individual molecules
Once the center of reactivity is identified, its
characteristic reactions are expected to occur

Functional Groups And Their Properties
Polar functional groups contain O and N

Like dissolves like: polar solvents will dissolve
the polar functional groups
As the carbon chain increases in size, the polarity
decreases

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

Lewis Structures Of Hydrocarbons
Show all atoms, and all electrons

Bond pairs usually shown as a line
Non-bonding (lone) pairs of electrons are shown
as dots
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)
All hetero-atoms are shown explicitly
Double bonds explicitly shown
H H H H H
H
C C C C C C
H C C H C C
H H HH

Learning Check
Fill in the missing atoms and derive the condensed

structure
O
C5H12 C4H8O2

Your Turn!
Which is the correct formula for the structure

shown?
A. C42H12
B. C24H12
C. C36G12
D. None of these

Alkanes & Alkenes Are Non-polar
Alkanes are hydrocarbons (contain only C and H)

have a ratio of atoms CnH2n+2
Alkenes- hydrocarbons with fewer H than the
alkanes (CnH2n)
Use the same prefixes, but have the suffix -ene.

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

Naming Alkanes
1. Find the longest continuous chain of carbons-the root.

2. a. Name the root by adding -ane to the appropriate
prefix (a 4-carbon chain would be butane)
b. Identify any branches, and name each by the
number of carbons (a 1-carbon branch is methyl-)
3. a. List side chains in alphabetical order, before the
root
b. Use di, tri, tetra (etc) if you have more than one
of something (these do not count in alphabetizing)

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

Name the following
3-ethyl-2-methylhexane 2,3,3,4-tetramethylhexane
3-methylheptane 3-ethyl-4-methylhexane

Your Turn!
Name the structure shown:

A. 1,2-dimethylpentane
B. 3-methylhexane
C. 2-ethylpentane
D. None of these

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)
CH4 high
C 2H2
temperature
CH3CH3 high
H2C CH2 H2
temperature
ethane ethene

Unsaturated Hydrocarbons
Hydrocarbons with one or more double bonds are
members of the alkene family
open chain alkenes have the general formula C2H2n
Hydrocarbons with triple bonds are in the alkyne
family
open chain alkynes have the general formula, CnH2n2

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

Name The Following
ethylene 2,3-dimethyl-1-pentene
Your Turn!
Which name is not correct?
A. 3-pentene
B.
2-pentene
C.
2-methyl-1-butene
D. All are correct
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

Your Turn
Which isomer is shown:
A. cis-
B. trans-
C. cant tell

Addition Reactions of Alkenes
Alkenes undergo addition reactions that eliminate the
pi-bond
CH2=CH2 + HCl(g) Cl- CH2-CH3
Inorganic compounds that undergo addition reactions
with alkenes include: H2O, Cl2, Br2, I2, and H2.
Ozone (O3) reacts with anything that has a carbon-
carbon double or triple bond, forming a variety of
products

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

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 dimethyl ether
CH3CH2OCH3 ethyl methyl ether
CH3CH2OCH2CH3 diethyl ether
22.3. Ethers and alcohols are organic derivatives of water 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 ethanol
CH3CH2CH2CH2OH butanol

Oxidation of Alcohols
If the alcohol carbon atom holds at least one H atom, it

can be replaced with bonds to oxygen
O O
|| Further ||
RCH 2OH
R C H
R C OH
oxidation oxidation
alcohol aldehyde carboxylic acid

O O
|| Further ||
CH 3CH 2OH oxidation
CH 3 C H
CH 3 C OH oxidation

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
| |
H OH
22.3.Ethers and alcohols are organic derivatives of water 38

Substitution Reactions Of Alcohols
Under acidic conditions, the -OH group can be

replaced by a halogen atom
CH 3CH 2CH 2OH HBr(conc) CH 3CH 2CH 2 Br H 2O

1 - propanol 1 - bromopropane

Your Turn!
What type of structure is shown

A. Alcohol
B. Ether
C. Peroxide
D. aldehyde

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).
Amines are bases, and react with strong proton
donors to form ammonium ion-like structures
NH3(aq) H (aq) NH4 (aq)
CH3CH2NH2 (aq) H (aq) CH3CH2NH3 (aq)
22.4. Amines are organic derivatives of ammonia 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
22.4. Amines are organic derivatives of ammonia 42

Aldehydes
The IUPAC name ending for an aldehyde is al
The parent chain is the longest chain that includes
the aldehyde group
O O O
|| || ||
HCH CH 3 C H CH 3CH 2 C H
methanal ethanal propanal
22.5. Organic compounds with carbonyl groups include aldehydes, ketones, and 43
carboxylic acids
Ketones
The IUPAC ending for ketones is one.

The parent chain must include the
carbonyl group
O O
|| ||
CH 3 C CH 3 CH 3CH 2 C CH 2CH 3
propanone 3-pentanone
carboxylic acids
Reactions Of Aldehydes & Ketones
Aldehydes and ketones can be hydrogenated to

give alcohols
O
||
CH3CH3 C H H2 CH3CH2 CH2OH 1 - propanol
O OH
|| |
CH3 C CH3 H2 CH3 C H CH3 2 - propanol
Aldehydes undergo oxidation to form
carboxylic acids, while ketones strongly resist
oxidation
carboxylic acids
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
O O
|| ||
H C OH CH3CH 2 C OH
methanoicacid ethanoicacid
The common names are used for these: formic
acid and acetic acid
carboxylic acids
Your Turn!
Which of the following contain a carbonyl group?

A. amine
B. amide
C. carboxylic acid
D. All contain a carbonyl
carboxylic acids
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
O O
|| ||
H C OCH3 CH3 C OCH2CH3
methyl methanoate ethyl ethanoate
carboxylic acids
Preparation Of Esters
Esters can be prepared by heating the parent acid with

an alcohol in the presence of an acid catalyst
O O
|| ||
H
R C OH HOR' R C OR' H 2O
O O
|| ||
H
CH 3 CH 2 C OH HOCH 2CH 3 CH 3 CH 2 C OCH 2CH 3 H 2O
ethanoic acid ethanol ethyl ethanoate
carboxylic acids
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
||
CH 3 CH 2 C OCH 2CH 3 (aq) NaOH (aq) heat

ethyl ethanoate
O
||
CH 3 CH 2 C O (aq) Na (aq) CH 3CH 2OH
ethanoate ion ethanol
carboxylic acids
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
H 2N
O
O
NH 2
propanamide 2-methyl-butanamide
carboxylic acids
Preparation of Amides
One way to prepare simple amides is by heating

a carboxylic acid in excess ammonia
O O
|| ||
R C OH NH 3
R C NH 2 H 2O
heat
O O
|| ||
CH 3CH 2 C OH NH 3
CH 3CH 2 C NH 2 H 2O
heat
propanoic acid propanamide
carboxylic acids
Reactions of Amides
Amides, like esters, can be hydrolyzed

O O
|| ||
R C NH 2 H 2O
R C OH NH 3
heat
O O
|| ||
CH 3CH 2 C NH 2 H 2O
CH 3CH 2 C OH NH 3
heat
propanamide propanoic acid

Amides are not bases; the O on the carbonyl draws
electron density to itself and tightens the unshared
electrons on N, preventing their donation
carboxylic acids
Your Turn!
Which of these can be hydrolyzed (react with water)

A. amides
B. alkanes
C. alcohols
D. None of these
carboxylic acids
Polymers
Are large molecules with repeating units called

monomers
22.6. Polymers are composed of many repeating molecular units 55

Formation Of Addition Polymers
Initiators attack a monomer and make it receptive

for the new bond
Addition polymers are assembled from molecular

units that combine to form one larger molecule

Addition Polymer: Polystyrene
Styrene is treated with an initiator to form a free

radical
Radical end is free to form a new connection to
another styrene molecule

Formation Of Condensation Polymers
Condensation polymers are formed when monomers

add and lose a small molecule
adipic acid and hexamethylene diamine combine
and eliminate water to form Nylon 6,6
The ends are free to continue the process

Crosslinking
Branches on polymers
make them susceptible
to interaction with other
polymers
Increased crosslinking
leads to increased
strength
The concept behind
vulcanized rubber

Learning Check: Teflon
Is formed from the monomer F2CCF2 . Based on

the structure of polytetrafluoroethylene (PFTE), is
this an addition or a condensation polymer?
addition

The Polyethylenes: LDPE, HDPE and
UHMWPE
Have widely disparate
properties due to the degree of
order
low density (LD) PE with an
unordered crystal, is used for
grocery sacks
high density (HD) PE with
highly structured crystal is
very strong and used in
TYVEK
ultra-high molecular weight
(UHMW) PE has very long
HDPE fibers and is used in
bulletproof vests and sails
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

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

Carbohydrates
Are naturally occurring polyhydroxyaldehydes or

polyhydroxyketones, or else compounds that react
with water to give these
Types:
monosaccharides
disaccharides
polysaccharides
22.7. Most biochemicals are organic compounds 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
H2
HO C OH
OH OH OH
HC CH
H2C H C H C
C H C H CH HO CH O
HC CH
OH OH O
HO OH
glucose (open chain polyhydroxyaldehyde) -glucose

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

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)

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
Cellulose, a chief component of plant cell walls,
is a polymer of glucose that requires a special
enzyme to hydrolyze
humans lack this enzyme and so are unable to use
cellulose for food
cellulose is the fiber found in foods like lettuce

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

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

Glycerophospholipids
The lipids involved in animal cell membrane are called

glycerophospholipids
The lipid molecules of animal cell membranes are organized as a bilayer.

Your Turn!
Which are forms of fats?

A. Lipids
B. Glycerols
C. Polysaccharides
D. All of these

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

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
Enzymes are the catalysts in living cells
Virtually all enzymes are proteins

Nucleic Acids
Carry the genetic

code
Are made of amino
acids
22.8. Nucleic acids carry our genetic information 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
DNA replicates itself by splitting the parent DNA
double helix and assembling the matching base pairs
on each strand
The result is two daughter DNA double helixes

Replication of DNA

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

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
Transcription: the genetic message is read off in the cell
nucleus and transferred to ribonucleic acid (RNA)
Translation: the genetic message, now on RNA outside the
nucleus, is used to direct the synthesis of a polypeptide

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
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
Atomic radiation and chemical agents can also
cause defects, possibly causing cancer

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

Your Turn!
How many types of RNA are there in a living

organism?
A. 1
B. 2
C. 3
D. 4

Your Turn!
How many types of DNA are there in a living

organism?
A. 1
B. 2
C. 3
D. 4

Ch10-Organic Compounds, Polymers, and Biochemicals

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Ch 22.

Brady & Senese, 5th Ed.

22.1. Organic chemistry is the study of carbon compounds

Carbon compounds are greatly variant due to the

22.1. Organic chemistry is the study of carbon compounds 3

Carbon containing compounds exist in large

22.1. Organic chemistry is the study of carbon compounds 4

show the general arrangement of the atoms and the

22.1. Organic chemistry is the study of carbon compounds 6

Contain C, H, and O, all with single bonds.

22.1. Organic chemistry is the study of carbon compounds 7

22.1. Organic chemistry is the study of carbon compounds 8

Each has a carbon chain terminating in a carbonyl.

22.1. Organic chemistry is the study of carbon compounds 9

Amines contain -NH2 on carbon chain (RNHR)

22.1. Organic chemistry is the study of carbon compounds 10

Both have a carbon chain terminating in a

22.1. Organic chemistry is the study of carbon compounds 11

22.1. Organic chemistry is the study of carbon compounds 12

Collecting molecules into families means that only

22.1. Organic chemistry is the study of carbon compounds 13

Polar functional groups contain O and N

22.1. Organic chemistry is the study of carbon compounds 14

Which of the following

22.1. Organic chemistry is the study of carbon compounds 15

Show all atoms, and all electrons

Each vertex and terminus is a carbon

22.2. Hydrocarbons consist of only C and H atoms 17

Fill in the missing atoms and derive the condensed

22.2. Hydrocarbons consist of only C and H atoms 18

Which is the correct formula for the structure

22.2. Hydrocarbons consist of only C and H atoms 19

Alkanes are hydrocarbons (contain only C and H)

22.2. Hydrocarbons consist of only C and H atoms 20

Composed of hydrocarbon chains in which carbons

22.2. Hydrocarbons consist of only C and H atoms 21

1. Find the longest continuous chain of carbons-the root.

22.2. Hydrocarbons consist of only C and H atoms 22

4. Number root from side closest to the first

22.2. Hydrocarbons consist of only C and H atoms 23

22.2. Hydrocarbons consist of only C and H atoms 24

Name the structure shown:

22.2. Hydrocarbons consist of only C and H atoms 25

22.2. Hydrocarbons consist of only C and H atoms 26

22.2. Hydrocarbons consist of only C and H atoms 27

The parent chain must include the double bond

22.2. Hydrocarbons consist of only C and H atoms 28

Cis and trans isomers exist when there

22.2. Hydrocarbons consist of only C and H atoms 31

22.2. Hydrocarbons consist of only C and H atoms 32

22.2. Hydrocarbons consist of only C and H atoms 33

22.2. Hydrocarbons consist of only C and H atoms 34

22.3. Ethers and alcohols are organic derivatives of water 35

22.3. Ethers and alcohols are organic derivatives of water 36

If the alcohol carbon atom holds at least one H atom, it

alcohol aldehyde carboxylic acid

22.3. Ethers and alcohols are organic derivatives of water 37

The reverse the the addition of water to an

22.3.Ethers and alcohols are organic derivatives of water 38

Under acidic conditions, the -OH group can be

CH 3CH 2CH 2OH HBr(conc) CH 3CH 2CH 2 Br H 2O

22.3. Ethers and alcohols are organic derivatives of water 39

What type of structure is shown