Chapter 22

Organic Chemistry!!!!!
Chapter 6 in rxn workbook
Chapter 16 in PR

1
Organic Chemistry Is…..
 The study of carbon
containing compounds
and their properties

 Organic compounds are

typically in chains or
rings

 All organic molecules

are produced by living
things/systems
2
Vocabulary
 Chain

 Parent chain and

substituent

3
The Name Game …again
 Alkanes = hydrocarbons (chains of C and H)

 All bonds are single i.e “Saturated”

 An alkane is a hydrocarbon in which each

carbon atom is bonded to four other carbon
or hydrogen atoms.

4
10 “normal” alkanes

5
The Rest
Pentane C5H12
Hexane C6H14
Heptane C7H16
Octane C8H18
Nonane C9H20
Decane C10H22

A note on Boiling Point:

BP Octane C8H18 < Nonane C9H20
More C = more bonds to break and more energy
required. 6
 Isomers
 Same number and
type of molecules
but bonded in a
different location

7
Draw all isomers Pentane

4
2 3 5
1

8
9
 IUPAC
International Union of Pure and Applied Chemistry

10
Rules for Naming Alkanes
 Read Page 1061
 For chain alkanes beyond butane add the
suffix –ane to the Greek root for the number
of carbons

11
For Branched alkanes find the longest
continuous carbon chain and use this name
as the base
(a). If two chains of equal length are present,
choose the one with the more branch points
as the parent.

12
 When alkane groups appear as substituent
groups they are named by dropping the
-ane and adding –yl.

 For example CH3 (methane) = methyl . C3H7

is called propyl

13
 The position of substituent groups are
specified by numbering the longest chain of
carbon atoms sequentially starting at the end
with the closest branching.
C
C-C-C-C-C-C
1 2 3 4 5 6 correct numbering
6 5 4 3 2 1 incorrect numbering

14
Last rule!
 The location and name of each substituent is
followed by the root alkane name.

 Substituents are listed in alphabetical order

and the prefixes (di, tri,) are used to indicate
multiple identical substituents.

 A number denotes which carbon that

substituent is boned to.
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Example
CH3
CH3 – CH2 - CH – CH2 – CH2 - CH3
1 2 3 4 5 6

3 - methylhexane

Smallest number for substituent

Substituent name
Parent chain root name
Hyphen between number and substituent name
16
Try some
 Draw all structural isomers or C H
6 14

1. Start with the longest chain and then

rearrange the carbons to form the shorter

CH3-CH2 -CH2 -CH2 –CH2-CH3

1 2 3 4 5 6

Hexane
17
Take one carbon out of the chain and make it a methyl
substituent

CH3
CH3-CH2 -CH -CH2 –CH3 2 - methylpetane
1 2 3 4 5

CH3
CH3-CH –CH2 -CH2 –CH3 3 - methylpetane
18
Next take two carbons out of the chain

CH3
CH3-C –CH -CH3 2,2-dimethylbutane
CH3
1 2 3 4

CH3 CH3
CH3-CH –CH -CH3 2,3-dimethylbutane
1 2 3 4

19
Write the structure for each of the
following compounds
 4-ethyl-3,5-dimethylnonane

(note the substituents are in alphabetical order

separated by a dashed line)

 4-tert-butylheptane

 (see your cheat sheet for tert structure)

20
4-ethyl-3,5-dimethylnonane

1 4 9

21
4-tert-butylheptane

1 2 3 4 5 6 7
CH3-CH2-CH2-CH-CH2-CH2- CH3
H3C-C-CH3
CH3

22
Reactions of Alkanes
 Combustion reaction
 Substitution reactions
 Dehydration reactions

 page1065

23
Cyclic Alkanes

Add Cyclo to the number of carbons present

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25
Naming cyclic structures with
substituent
 Give substituent the lowest number possible
(can start with one this time)

 If more than one substituent is present

number in alphabetical order insuring that all
substituents have the lowest possible number

26
27
Homework
Read Page 1066 sample exercise 22.4 naming
cyclic alkanes

Do page 1100 #’s: 15, 17, 19, 20,

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22.2 Alkenes and alkynes
 Hydrocarbons that contain carbon carbon
double bonds.

C2H4

C2H2

29
Rules for naming Alkenes
 Root hydrocarbon chain ends in –ene

methene
Ethene
Propene
butene

30
 In alkenes with more than three carbons, the
location of the double bond is indicated by the
lowest numbered carbon atom INVOLVED in
the double bond.

CH2= CHCH2CH3 1-butene

CH3CH=CHCH3 2-butene

31
Double Bonding

σ sigma bond

π Pi bond

32
 Isomers of Alkenes
Cis:
H on
The same side of
The molecule

Trans:

H on
opposite sides of
the molecule
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34
Practice naming
Find the longest chain
and number it in the
direction that gives the
double bond the lowest
number.

Identify if the molecule is

cis or trans

4-methyl-cis-2-hexene

35
Alkynes
 Unsaturated hydrocarbons containing a
carbon-carbon triple bond.
 The simplest alkyne is C2H2 called acetylyne
 In a triple bond there is one sigma bond and
two pi bonds.
 Replace the –ane ending –yne
 Alkenes and alkynes can exist as ringed
structures as well.

36
37
2-methyl-3-heptyne

Due to the triple bond

there is no H to be cis
or trans

38
Homework
 Pg 1101 #’s : 21, 22, 23,24

39
Aromatic Hydrocarbons
 A special class of cyclic unsaturated
hydrocarbons.

 The simplest is benzene C6H6

40
Resonance of
Benzene

41
Nomenclature
 If there is more than one substituent numbers
are used to indicate position.

1,2,4-trichlorobenzene 2,4,6-trinitrotoluene (TNT)

42
FYI

Toluene or Methylbenzene
Common name IUPAC name
43
 Some systems use prefixes for substituent
position.

 Ortho (o) for two adjacent substituent

meta (m) two substituent with 1 carbon between

them.

para (p) two substituents opposite of each other

When benzene is used as a substituent it is

called a phenyl group.
44
0-dichlorobenzene m-dichlorobenzene p-dichlorobenzene

45
Give substituents lowest number and place
in alpha order.

o-bromochlorobenzene p-bromochlorobenzene
46
Complex aromatics pg 1072 table22.3

Naphthalene

Anthracene

Phenanthrene

47
48
Homework
 25, 27(skip d) ,28, 29, 37, 38

49
22.5 hydrocarbon Derivatives
 Molecules that are fundamentally
hydrocarbons (C&H) but have additional
atoms or groups of atoms called functional
groups

 Functional Group: functional groups are

specific groups of atoms with in molecules,
that are responsible for the characteristics of
those molecules

50
Common functional groups pg 1077
table 22.5
Class General Formula
 Halohydrocarbons RX
(x = F, Cl, Br, I)
 Alcohols ROH

 Ethers ROR

 Aldehydes

O
R C H
R and R’ = hydrocarbon fragments
51
The Common Functional Groups

Class General Formula

Ketones O
R C R'

Carboxylic Acids O
R C OH

Esters
O
R C O R'

Amines RNH2
52
53
Alcohols
 Have a hydroxyl group

 Replace final -e with –ol

 Position of –OH group is specified with a

number (smallest number goes to substituent)

 Classified according to how many

hydrocarbon fragments (R) they have

54
See table 22.6 for common alcohols

55
Example: Name and state 1º, 2º, 3º
 Number the chain
Giving OH smallest
number

Note carbon that –OH is

attached to has –CH3
and a -CH2CH3 groups
attached.

Thus it is a secondary
alcohol.
56
Name and state 1º, 2º, 3º

57
3-chloro-1-propanol

Primary alcohol
58
Phenol

59
Aldehydes and Ketones
 Aldehydes and ketones contain carbonyl
groups.

60
Ketones
 Carbonyl group bonded two carbons atoms
 Ex: acetone

61
Aldehydes
Carbonyl group is bonded to at least one
hydrogen

62
Naming Aldehydes and Ketones
 Aldehydes: Named from parent alkane and removing
the e and adding –al.

 Ketones: The final e is replaced with –one.

 In both cases a number indicates the position of the

carbonyl group where necessary.

 Note: since aldehyde functional group is always a the

end of the carbon chain the aldehyde carbon is
always assigned as number 1 for referencing the
substituent position in the name.
63
Naming Aldehydes and Ketones
 The parent chain selected must contain the
carbonyl group.

 Number the carbon chain, beginning at the

end nearest to the carbonyl group.

 Number the substituents and write the name,

listing substituents alphabetically.

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3

65
66
Carboxylic Acids
 Carboxylic Acids have a carboxyl group.

RCOOH
67
Naming carboxylic acids
 Name from parent alkane by dropping e and
adding -oic

68
Esters
 Carboxylic acid reacting with an alcohol to
form an ester.

 Sweet fruity smell (bananas, oranges)

Acetylsalicylic acid

69
Amines
 Have one carbon nitrogen bond. N-C

 1° one N-C bond

 2° two N-C bond
 3° three N-C bond

 Common names are often used rather than IUPAC

names.

 Fish like odor

70
methyl amine

ethyl amine

propyl amine

cyclobutyl amine

71
Homework
 Pg 1102-1103

 #’s: 41, 47, 49, 50

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