Chapter 22(a)
Organic and Biological
Molecules
Figure 22.1:
The C—H
bonds in
methane.
Figure 22.2:
(a) The Lewis
structure of
ethane (C2H6).
(b) The
molecular
structure of
ethane
represented by
space-filling and
ball-and-stick
models.
Figure 22.3: The structures of (a) propane
(CH3CH2CH3) and (b) butane (CH3CH2CH2CH3).
Each angle shown in red is 109.5º.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–4
Copyright © Houghton Mifflin Company. All rights reserved.
22a–5
Figure 22.4: (a) Normal butane (abbreviated
n-butane). (b) The branched isomer of
butane (called isobutane).
Copyright © Houghton Mifflin Company. All rights reserved.
22a–6
Normal pentane.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–7
Copyright © Houghton Mifflin Company. All rights reserved.
22a–8
Figure 22.5: (a)
The molecular
structure of
cyclopropane
(C3H6). (b) The
overlap of the
3
sp orbitals that
form the C—C
bonds in
cyclopropane.
Figure 22.6:
The (a) chair
and (b) boat
forms of
cyclohexane.
Figure 22.7: The bonding in ethylene.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–11
Figure 22.8: The bonding in ethane.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–12
Figure 22.9:
The two
stereoisomers
of 2-butene:
(a) cis-2butene and
(b) trans-2butene.
Figure 22.10: The bonding in acetylene.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–14
Figure 22.11: (a) The structure of benzene, a
planar ring system in which all bond angles are
120º. (b) Two of the resonance structures of
benzene. (c) The usual representation of benzene.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–15
Figure 22.12:
Some
selected
substituted
benzenes and
their names.
Common
names are
given in
parentheses.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–17
Chapter 22(b)
Organic and Biological
Molecules (cont’d)
Copyright © Houghton Mifflin Company. All rights reserved.
22a–19
Copyright © Houghton Mifflin Company. All rights reserved.
22a–20
Figure 22.13: Some common
ketones and aldehydes.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–21
Figure 22.14:
Some
carboxylic
acids.
Figure 22.15: The general formulas for primary,
secondary, and tertiary amines. R, R', and R"
represent carbon-containing substituents.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–24
A radio from the 1930’s made of Bakelite.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–25
A scanning electron microscope image showing the
fractured plane of a self-healing material with a
ruptured microcapsule in a thermosetting matrix.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–26
Copyright © Houghton Mifflin Company. All rights reserved.
22a–27
Figure 22.16: The reaction to form nylon can be carried out at
the interface of two immiscible liquid layers in a beaker. The
bottom layer contains adipoyl chloride, dissolved in CCl4, and
the top layer contains hexamethylenediamine, dissolved in
water. A molecule of HCl is formed as each C—N bond forms.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–28
Wallace H. Carothers
Copyright © Houghton Mifflin Company. All rights reserved.
22a–29
Figure 22.17: (a) A tube composed of HDPE is inserted into
the mold (die). (b) The die closes, sealing the bottom of the
tube. (c) Compressed air is forced into the warm HDPE
tube, which then expands to take the shape of the die. (d)
The molded bottle is removed from the die.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–30
Figure 22.18: The 20 a-amino acids found in
most proteins. The R group is
shown in color.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–31
Figure 22.18 (cont’d)
Copyright © Houghton Mifflin Company. All rights reserved.
22a–32
Figure 22.19: The amino acid sequences in
(a) oxytocin and (b) vasopressin. The
differing amino acids are boxed.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–33
Figure 22.20:
Hydrogen bonding
within a protein
chain causes it to
form a stable
helical structure
called the -helix.
Only the main
atoms in the helical
backbone are
shown here. The
hydrogen bonds
are not shown.
Chapter 22(c)
Organic and Biological
Molecules (cont’d)
Figure 22.21:
Ball-and-stick
model of a
portion of a
protein chain
in the -helical
arrangement,
showing the
hydrogenbonding
interactions.
Figure 22.22: When hydrogen bonding
occurs between protein chains rather than
within them, a stable structure (the pleated
sheet) results.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–37
Figure 22.23: (a) Collagen, a protein found in tendons,
consists of three protein chains. (b) The pleated-sheet
arrangement of many proteins bound together to form the
elongated protein found in silk fibers.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–38
Figure 22.24: Summary of the various types of interactions
that stabilize the tertiary structure of a protein: (a) ionic, (b)
hydrogen bonding, (c) covalent, (d) London dispersion, and
(e) dipole–dipole.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–39
Figure 22.25:
The permanent
waving of hair.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–41
Figure 22.26:
A schematic
representation
of the thermal
denaturation
of a protein.
Figure 22.27:
When a tetrahedral
carbon atom has
four different
substituents, there
is no way that its
mirror image can
be superimposed.
Figure 22.28: The mirror image optical
isomers of glyceraldehyde.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–44
Figure 22.29:
The cyclization
of D-fructose.
Figure 22.30: The cyclization of glucose. Two different rings
are possible; they differ in the orientation of the hydroxy
group and hydrogen on one carbon, as indicated. The two
forms are designated  and  and are shown here in two
representations.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–46
Figure 22.31: Sucrose is a disaccharide
formed from -D-glucose and fructose.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–47
Figure 22.32: (a) The polymer amylose is a
major component of starch and is made up of
-D-glucose monomers.(b) The polymer cellulose,
which consists of -D-glucose monomers.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–48
Figure 22.33:
The structure
of the
pentoses (a)
deoxyribose
and (b) ribose.
Figure 22.34: The organic bases found in
DNA and RNA.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–50
Figure 22.35: (a) Adenosine is formed by the
reaction of adenine with ribose. (b) The reaction of
phosphoric acid with adenosine to form the ester
adenosine 5-phosphoric acid, a nucleotide.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–51
Figure 22.36:
A portion of a
typical nucleic
acid chain.
Note that the
backbone
consists
of sugar–
phosphate
esters.
Figure 22.37: (a) The DNA double helix contains two
sugar–phosphate backbones, with the bases from the two
strands hydrogen-bonded to each other. The
complementarity of the (b) thymine-adenine and (c)
cytosine-guanine pairs.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–53
Figure 22.38:
During cell
division the
original DNA
double helix
unwinds and new
complementary
strands are
constructed on
each original
strand.
Figure 22.39: The mRNA molecule, constructed
from a specific gene on the DNA, is used as the
pattern to construct a given protein with the
assistance of ribosomes.
Copyright © Houghton Mifflin Company. All rights reserved.
22a–55