This document provides an overview of organic chemistry concepts including: - Carbon's unique properties allow it to form many diverse organic compounds. - Hydrocarbons are organic compounds made of carbon and hydrogen that exist as chains or rings. - Functional groups are atoms or groups that confer unique reactivity, including alcohols, aldehydes, ketones, carboxylic acids, esters, amines, and amides. - The three main types of organic reactions are addition, elimination, and substitution depending on changes in carbon bonding.

1. 15-1
Chapter 15
Organic Compounds and the Atomic
Properties of Carbon

2. 15-2
Organic Compounds and the Atomic Properties of Carbon
15.1 The special nature of carbon and the characteristics of
organic molecules
15.2 The structures and classes of hydrocarbons
15.3 Some important classes of organic reactions
15.4 Properties and reactivities of common functional groups
15.5 The monomer-polymer theme I: Synthetic macromolecules
15.6 The monomer-polymer theme II: Biological macromolecules

3. 15-3
Figure 15.1
The position of carbon in the periodic table

4. 15-4
Figure 15.2
The chemical diversity of organic compounds
4 carbons linked with single bonds, 1 oxygen and needed hydrogens.
CH3 CH2 CH2 CH2 OH
CH3 CH2 CH CH3
OH
CH3 CH2 CH2 O CH3
CH3 CH CH2 OH
CH3
CH3 C
OH
CH3
CH3
CH3 CH2 O CH2 CH3
CH3 CH
CH3
O CH3
CH3 CH CH CH3
O
H2
C
H2C CH CH2OH
H2
C
H2C CH CH2OH
CH2
CH2 CH2
CH
OH
CH2
CH CH2
O
CH3
H2C
H2C CH2
CH2
O

5. 15-5
CH3 CH2 CH2 C O
H
CH3 CH2 C CH3
O
CH2 CH CH2 CH3
O
C
H2C CH CH3
OH
H
Figure 15.2 (continued)
H2C
H2C CH
O
CH3
O
H2C C CH3
CH3
CH2
CH2 CH2
C
O
CH2
H2C CH C
H
O
C
H2C CH CH3
O
CH3 CH C
O
CH3
H

6. 15-6
HYDROCARBONS
Carbon skeletons and hydrogen skins
When determining the number of different skeletons, remember that:
 Each carbon forms a maximum of four single bonds, OR two
single and one double bond, OR one single and triple
bond.
 The arrangement of carbon atoms determines the skeleton,
so a straight chain and a bent chain represent the same
skeleton.
 Groups joined by single bonds can rotate, so a branch
pointing down is the same as one pointing up.

7. 15-7
Some five-carbon skeletons
Figure 15.3
single bonds double bonds ring structures

8. 15-8
Adding a H-atom skin to a carbon skeleton
Figure 15.4

9. 15-9
SAMPLE PROBLEM 15.1 Drawing hydrocarbons
PROBLEM: Draw structures that have different atom arrangements for
hydrocarbons with:
PLAN: Start with the longest chain and draw shorter chains until you
are repeating structures.
(a) six C atoms, no multiple bonds, and no rings
(b) four C atoms, one double bond, and no rings
(c) four C atoms, no multiple bonds, and one ring
SOLUTION: (a) six carbons, no rings
C C H
H
H
C
H
H
H
H
C
H
H
C
H
H
C
H
H
H C
H
H
C
C
H
C
H
H
C
H
H
C
H
H
H H
H
H H
C
H
H
C
H
H
C
H
C
H
H
C
H
H
H H
C
H
H H

10. 15-10
SAMPLE PROBLEM 15.1 (continued)
(a) continued:
C
C
C
C
C
C
C
C
C
C
C
C
(b) four carbons, one double bond
C C C C
H
H H H
H
H
H
H
C C C C
H
H H H
H
H
H
H
H C C C
H H
H
H
C H
H
H
(c) four carbons, one ring
C
C C
C
H
H
H
H
H
H
H
H
C
C C
C
H
H
H H
H
H H
H

11. 15-11
Table 15.1 Numerical Roots for Carbon Chains and Branches
number of
carbon atoms
roots
1
2
3
4
5
6
8
7
9
10
meth-
eth-
prop-
but-
hex-
pent-
hept-
oct-
non-
dec-

12. 15-12

13. 15-13
Figure 15.5
Ways to depict formulas and models of an alkane

14. 15-14
Figure 15.6
Depicting cycloalkanes
C
C C
H H
H
H
H
H
C
C C
C
H
H
H
H
H
H H
H
cyclopropane cyclobutane

15. 15-15
Figure 15.6
Depicting cycloalkanes
cyclopentane
cyclohexane
C C
C
C
C
H H
H
H
H
H
H
H
H
H C
C
C
C
C
C
H H
H H
H
H
H
H
H
H
H
H

16. 15-16

17. 15-17
Figure 15.7
Boiling points of the first 10 unbranched alkanes

18. 15-18
Figure 15.8
An analogy for
optical isomers

19. 15-19
Figure 15.9
Two chiral molecules
optical isomers of 3-methylhexane optical isomers of alanine

20. 15-20
Figure 15.10
The rotation of plane-polarized light by an optically active substance

21. 15-21
Figure 15.11
The binding site
of an enzyme

22. 15-22

23. 15-23
Figure B15.1
The initial chemical event in vision

24. 15-24
SAMPLE PROBLEM 15.2 Naming alkanes, alkenes and alkynes
PROBLEM: Give the systematic name for each of the following, indicate
the chiral center in part (d), and draw two geometric isomers
for part (c).
(a)
CH3 C
CH3
CH3
CH2 CH3 CH3 CH2 CH CH
CH3
CH3
CH2
CH3
(b) CH3
CH2CH3
(c)
CH3 CH2 CH CH
CH3
CH2
(d)
CH2 CH C CH
CH3
CH3
CH3
CH3
(e)
PLAN: For (a)-(c), find the longest, continuous chain and give it the base
name (root + suffix). Then number the chain so that the branches
occur on the lowest numbered carbons and name the branches with
the (root + yl). For (d) and (e) the main chain must contain the double
bond and the chain must be numbered such that the double bond
occurs on the lowest numbered carbon.

25. 15-25
SAMPLE PROBLEM 15.2
SOLUTION:
(continued)
(a)
CH3 C
CH3
CH3
CH2 CH3
butane
methyl
methyl
1 4
3
2
2,2-dimethylbutane
CH3 CH2 CH CH
CH3
CH3
CH2
CH3
(b)
hexane
methyl
methyl
1
2
3
4
5
6
3,4-dimethylhexane
(can be numbered in either direction)
CH3
CH2CH3
(c)
cyclopentane
methyl
ethyl
1
2
3
4
5
1-ethyl-2-methylcyclopentane
CH3 CH2 CH CH
CH3
CH2
(d)
methyl
1
2
3
4
5
pentene
1-pentene
3-methyl-1-pentene
chiral center

26. 15-26
SAMPLE PROBLEM 15.2 (continued)
CH2 CH C CH
CH3
CH3
CH3
CH3
(e)
methyl
methyl
1
2
3
4
5
6
3-hexene
CH2
C C
CH
CH3
CH3
CH3
CH3
methyl
methyl
1
2
3
4
5
6
3-hexene
H
cis-2,3-dimethyl-3-hexene
CH2
C C
CH
CH3
CH3
CH3
CH3
methyl
methyl
1
2
3
4
5
6
3-hexene
H
trans-2,3-dimethyl-3-hexene

27. 15-27
Figure 15.12
Representations of benzene
or

28. 15-28
Types of organic reactions
An addition reaction occurs when an unsaturated reactant becomes a
saturated product:
Elimination reactions are the opposite of addition; they occur when a
more saturated reactant becomes a less saturated product:
R CH CH R + X Y R CH CH R
X Y
R CH CH R + X Y
R CH CH R
X Y
A substitution reaction occurs when an atom (or group) from an added
reagent substitutes for one in the organic reactant:
R C X + Y R C Y + X

29. 15-29
Figure 15.13
C C + Br2
A color test for
C=C bonds

30. 15-30
C C
Br
Br

31. 15-31
SAMPLE PROBLEM 15.3 Recognizing the type of organic reaction
PROBLEM: State whether each reaction is an addition, elimination, or
substitution:
(a) CH3 CH2 CH2 Br CH3 CH CH2 + HBr
(b) + H2
CH3 C Br
O
+ CH3CH2OH
(c)
CH3 C OCH2CH3 + HBr
O
PLAN: Look for changes in the number of atoms attached to carbon.
 More atoms bonded to carbon is an addition.
 Fewer atoms bonded to carbon is an elimination.
 Same number of atoms bonded to carbon is a substitution.

32. 15-32
SAMPLE PROBLEM 15.3
SOLUTION:
(continued)
(a) CH3 CH2 CH2 Br CH3 CH CH2 + HBr
Elimination: there are fewer bonds to last two carbons.
(b) + H2
Addition: there are more bonds to the two carbons
in the second structure.
CH3 C Br
O
+ CH3CH2OH
(c)
CH3 C OCH2CH3 + HBr
O
Substitution: the C-Br bond becomes a C-O bond
and the number of bonds to carbon remains the same.

33. 15-33
Figure 15.14
Some molecules with the alcohol functional group

34. 15-34

35. 15-35

36. 15-36
Figure 15.15
General structures of amines
primary (1o) amine secondary( 2o) amine tertiary (3o) amine
C N
the amine functional group

37. 15-37
Figure 15.16
Some biomolecules with the amine functional group
lysine (1o amine)
(amino acid found
in proteins)
adenine (1o amine)
(component of
nucleic acids)
epinephrine
(adrenaline; 2o amine)
(neurotransmitter in
brain; hormone released
during stress)
cocaine (3o amine)
(brain stimulant;
widely abused drug)

38. 15-38
Figure 15.17
Structure of a cationic detergent
CH
N CH3
H3C
H2C
CH2
H2C
CH2
H2C
CH2
H2C
CH2
H2C
CH2
H2C
CH2
H2C
CH2
H2C
CH3
Cl
benzylcetyldimethyl-
ammonium chloride

39. 15-39
SAMPLE PROBLEM 15.4 Predicting the reactions of alcohols, alkyl
halides, and amines
PROBLEM: Determine the reaction type and predict the product(s) in the
following:
(a) CH3 CH2 CH2 I + NaOH
(b) CH3 CH2 Br + 2H3C CH2 CH2 NH2
H3C CH CH3
OH
(c)
Cr2O7
2-
H2SO4
PLAN: Check for functional groups and reagents, then for inorganics added.
In (a) the -OH will substitute in the alkyl halide; in (b) the amine and
alkyl halide will undergo a substitution of amine for halogen; in (c)
the inorganics form a strong oxidizing agent resulting in an
elimination.

40. 15-40
SAMPLE PROBLEM 15.4 (continued)
SOLUTION:
(a) substitution - the products are: CH3 CH2 CH2 OH + NaI
(b) substitution - the products are: CH3 CH2 NHCH2CH2CH3
+ CH3CH2CH2NHBr
(c) elimination - the product is: H3C C CH3
O

41. 15-41
Figure 15.18
Some common aldehydes and ketones
methanal
(formaldehyde)
used to make
resins in
plywood,
dishware,
countertops;
biological
preservative
ethanal
(acetaldehyde)
narcotic product
of ethanol
metabolism;
used to make
perfume,
flavors, plastics,
other chemicals
benzaldehyde
artificial
almond
flavoring
2-propanone
(acetone) solvent
for fat, rubber,
plastic, varnish,
lacquer;
chemical
feedstock
2-butanone
(methyl ethyl
ketone)
important
solvent

42. 15-42
Figure 15.19
The carbonyl group

43. 15-43
SAMPLE PROBLEM 15.5
SOLUTION:
Predicting the steps in a reaction sequence
PROBLEM: Fill in the blanks in the following reaction sequence:
CH3 CH2 CH CH3
Br OH- Cr2O7
2-
H2SO4
CH3Li H2O
PLAN: Look at the functional groups and reagents to determine the type of
reaction.
CH3 CH2 CH CH3
Br
OH-
2-bromobutane
CH3 CH2 CH CH3
OH
2-butanol
Cr2O7
2-
H2SO4
CH3 CH2 C CH3
O
2-butanone
CH3Li
H2O
CH3 CH2 C CH3
OH
CH3
2-methyl-2-butanol

44. 15-44
Figure 15.20
Some molecules with the carboxylic acid functional group
methanoic acid
(formic acid)
(an irritating
component of ant
and bee stings)
butanoic acid
(butyric acid)
(odor of rancid butter;
suspected component
of monkey sex
attractant)
octadecanoic acid
(stearic acid)
(found in animal fats;
used in making
candles and soap)
benzoic acid
(calorimetric
standard; used in
preserving food,
dyeing fabric,
curing tobacco)

45. 15-45
Figure 15.21
Some lipid molecules with the ester functional group
cetyl palmitate
(the most
common lipid in
whale blubber)
lecithin
(phospholipid found in all cell membranes)
tristearin
(typical dietary fat used as an
energy store in animals)

46. 15-46
Figure 15.22
Which reactant contributes which group to the ester?
R C OH
O
R' OH
18
+ R C O
O
R'
18
+ H O H
R C OH
O
R' OH
18
+ R C O
O
R' + H O H
18
R C OH
O
H OR'
+ R C O
O
R' + H O H
H+
General esterification reaction

47. 15-47
lysergic acid diethylamide
(LSD-25)
(a potent hallucinogen)
Figure 15.23
Some molecules with the amide functional group
N,N-dimethylmethanamide
(dimethylformamide)
(major organic solvent;
used in production of
synthetic fibers)
acetaminophen
(active ingredient in
nonaspirin pain relievers;
used to make dyes and
photographic chemicals)

48. 15-48
SAMPLE PROBLEM 15.6
SOLUTION:
Predicting the reactions of the carboxylic
acid family
PROBLEM: Predict the product(s) of the following reactions:
CH3 CH2 CH2 C
O
OH CH3 CH CH3
OH
+
H+
(a)
CH3 CH CH2 CH2
(b)
CH3
C NH
O
CH2 CH3
NaOH
H2O
PLAN: (a) An acid and an alcohol undergo a condensation reaction to form
an ester.
(b) An amide, in the presence of base and water, is hydrolyzed.
CH3 CH2 CH2 C
O
O
(a) CH
CH3
CH3
CH3 CH CH2 CH2
(b)
CH3
C NH2
O
CH2 CH3
O-
+ Na+
+

49. 15-49
Figure 15.24
The formation of
carboxylic,
phosphoric, and
sulfuric acid
anhydrides

50. 15-50
Figure 15.25
An ester and an amide of other non-metals
glucose-6-phosphate sulfanilamide

51. 15-51
SAMPLE PROBLEM 15.7
PROBLEM:
SOLUTION:
Recognizing functional groups
Circle and name the functional groups in the following molecules:
(a)
C
O
O
OH
C CH3
O
(b)
CH
OH
CH2 NH CH3
(c)
Cl
O
PLAN: Use Table 15.5 to identify the functional groups.
(a)
C
O
O
OH
C CH3
O
carboxylic
acid
ester
(b)
CH
OH
CH2 NH CH3
alcohol
2o amine
(c)
Cl
O
ketone
alkene
haloalkane

52. 15-52
Figure 15.26
A summary of the interconversions among the major
organic functional groups

53. 15-53
Figure 15.27
Steps in the free-radical polymerization of ethylene

54. 15-54

55. 15-55

56. 15-56
Figure 15.28
The formation of nylon-66

57. 15-57
Figure 15.29
The structure of glucose in aqueous solution and the
formation of a disaccharide

58. 15-58
Figure 15.30
The common amino acids

59. 15-59
Figure 15.31
A portion of a polypeptide chain

60. 15-60
Figure 15.32
Forces that
maintain
protein
structure

61. 15-61
Figure 15.33
collagen
silk
fibroin
Shapes of
fibrous
proteins

62. 15-62
Figure 15.34
mononucleotide of
ribonucleic acid (RNA)
mononucleotide of
deoxyribonucleic acid
(DNA)
portion of DNA
polynucleotide chain
Mononucleotide monomers and their linkage

63. 15-63
Figure 15.35
The double helix of DNA
1.08 nm
1.08 nm

64. 15-64
Figure 15.36
Key stages in protein synthesis

65. 15-65 Figure 15.37
Key stages of DNA replication