Chem110: Chapters 24, 25 Organic Chemistry

Chem110
Chapters 24, 25
Organic Chemistry
copyright of chemistry 110 development team 1

Objectives By the end of this chapter you should be able to:
• Classify the organic compounds
• Differentiate between Aliphatic and Aromatic

Hydrocarbons
• Naming different organic compounds
• Know the chemistry of functional groups
• Know the Proteins

2
24.1 Classes of Organic Compounds
24.2 Aliphatic Hydrocarbons
 Alkane
Outline
 cycloalkane
 Alkenes
 Alkynes
24.3 Aromatic Hydrocarbon
24.4 Chemistry of Functional Groups
 Alcohol , ethers , aldehyde, ketones, carboxylic acid,
and esters
25.3 Proteins

24.1 Classes of Organic Compounds Chem
110
• Organic Chemistry: is the chemistry of carbon compounds.
Carbon has the ability to form long chains and ring structure.
• Hydrocarbons: compounds made of carbon and hydrogen only.
• Aliphatic Hydrocarbons: Do not contain benzene group.

• Aromatic Hydrocarbons: contain one or more benzene rings

24.2 Aliphatic Hydrocarbons
Chem
• Aliphatic hydrocarbons divided into:
110
• Alkanes: Only single covalent bonds are present, general
formula CnH2n+2, n = 1, 2, ….
• Cycloalkanes: alkanes whose carbon atoms are joined in

rings, general formula CnH2n, n = 3, 4, ….
• Alkenes: contain at least one carbon-carbon double bond,

general formula CnH2n, n = 2, 3 ….
• Alkynes: contain at least one carbon-carbon triple bond,

general formula CnH2n-2, n = 2, 3 ….
24.2 Aliphatic Hydrocarbons Chem
• Aliphatic hydrocarbons divided into: 110
Name Definition General Formula
Alkane Only single covalent bonds are CnH2n+2

present n = 1, 2, ….
Cycloalkanes The carbon atoms are joined in CnH2n

rings n = 3, 4, ….
Alkenes contain at least one C-C double CnH2n

bond n = 2, 3, ….
Alkynes contain at least one C-C triple CnH2n-2

bond n = 2, 3 ….

Alkanes: Chem
 The general formula CnH2n+2 where n = 1,2,3,…
110
 only single covalent bonds
 Saturated hydrocarbons
CH4 C2H6 C3H8
methane ethane propane

Alkane Chem
110

Q: C10H22 is the formula of an: Chem
a. alkane. 110
b. alkene.
c. alkyne.
d. aromatic hydrocarbon.
Q: A molecule with the formula C3H8 is a(n):

a. hexane
b. propane
c. decane
d. butane

Alkyl groups Chem
110

Alkanes Nomenclature Chem
110
• IUPAC: International Union of Pure and Applied Chemistry
1. Choose the longest chain in alkane
CH3
CH3 CH2 CH2 CH CH2 CH2 CH3

1 2 3 4 5 6 7
4-methylheptane

Chem
Start numbering from the nearest branching side .2
110
CH3
CH3 CH CH2 CH2 CH3

1 2 3 4 5
2-methylpentane
CH3
CH3 CH2 CH2 CH CH3

1 2 3 4 5
4-methylpentane

Chem
3. If there is more thane one group of same
substituent give the prefix di-, tri-, tetra- 110
p.63
CH3 CH3
CH3 CH CH CH2 CH2 CH3

1 2 3 4 5 6
2,3-dimethylhexane
CH3
CH3 CH C CH2 CH2 CH3

1 2 3 4 5 6
CH3
3,3-dimethylhexane
Chem
4- If there are two different substituent or more, start numbering
110
from the nearest side to the branch with consideration to the
alphabetical order.
Br CH3
CH3 CH CH2 CH2 CH CH3
2-bromo-5-methylhexane

Br NO2
Chem
110
CH3 CH CH CH3
1 2 3 4
2-bromo-3-nitrobutane
NO2 Br
CH2 CH2 CH CH3

1 2 3 4
3-bromo-1-nitrobutane

Chem
Q: The systematic name for 110
is 1-ethyl-2-methylbutane. Fals
Answer: 3,3-dimethylpentane

Example 24.2 p1030:
Chem
Give the IUPAC name of the following compound: 110
Solution:
2,2,4-trimethylhexane
Example 24.3 p1030: Chem
110
Write the structural formula of
3-ethyl-2,2-dimethylpentane
Solution:

Q: What is the IUPAC name of the following compound? Chem
CH3 C2H5 110
CH3 CH CH2 CH CH2 CH2 CH2 CH3
1 2 3 4 5 6 7 8
5-ethyl-2-methyloctane
Q: What is the structure of 2-propyl-4-methylhexane?
C 3H 7 CH3
CH3 CH CH2 CH CH2 CH3

1 2 3 4 5 6

Structural Isomers Chem
• Structural isomers: are molecules that have the 110
same molecular formula but different structures
C2H 6O
C4H10
CH3CH 2OH CH3OCH3
butan isobutane
2 chain isomers 2 Functional gp isomers

Structural Isomers of Alkanes Chem
110
# carbons Name # isomers
1 Methane 1
2 Ethane 1
3 Propane 1
4 Butane 2
5 Pentane 3
6 Hexane 5
7 Heptane 9
8 Octane 18
20 Eicosane 366,319
Example 24.1 p.1027: H.W. Chem
How many structural isomers does pentane, C5H12, have?
110
H H H H H
H C C C C C H
H H H H H
H CH3 H
n-pentane
H C C C H
H CH3 H H H CH3 H
H C C C C H 2,2-dimethylpropane
H H H H
2-methylbutane
Cycloalkanes Chem
 Alkanes whose carbon atoms are joined in rings are called
110
cycloalkanes.
 The general formula: is CnH2n where n = 3,4,…

Alkenes Chem
 Alkenes: at lease one C-C double bond is present. 110
 The general formula: is CnH2n where n = 2,3,4,…
ethene or ethylene
H2C = CH2
CH2 CH CH2 CH3 CH3 CH CH CH3

1-butene 2-butene

Alkene Nomenclature Chem
 Start numbering from nearest side to 110
the double bond
CH3 CH C CH2 CH2 CH2 CH3

CH3
methyl-2-heptene-3
CH3 CH CH CH CH3
Br
4-bromo-2-pentene
Q: Name the following compound: Chem
110
CH2 CH CH2 CH CH2
1,4-pentadiene

Geometric Isomers of Alkenes Chem
110
Cl Cl Cl H
C C C C
H H H Cl
cis-dichloroethylene trans-dichloroethylene
Same side Different sides

Q: Which of the following compounds has geometrical
isomer? Chem
H Cl H Cl
110
C C C C
H H H Cl
NO NO
NO2 Cl NO2 Cl
C C C C
H Cl H H
yes
NO
Cl Cl
C C
H H
yes
Q: For which of the compounds below are cis- Chem
trans isomers possible? 110
CH3CH=CH2 CH3CH=CHCH2CH3 CH3CH=CHCH3
(1) (2) (3)

• only 2
• both 1 and 2
• both 2 and 3
• all three only 3

Q: Which of the following does NOT exhibit Chem
geometric isomerism? (Hint: draw them!) 110
A. 4-octene
B. 2-pentene
C. 3-hexene
D. 2-hexene
E. 1-hexene

:Q: Write the structural formulas for the following compounds Chem
110
(a) trans -2-pentene (b) 2-ethyl-1-butene
H3 C H H C H2 C H3
C C C C
H C H2 C H3 H C H2 C H3
(c) 4-ethyl- trans -2-heptene
C H3 H
C C
H C HC H2 C H2 C H3
C H2 C H3

Alkynes Chem
 Alkynes: at lease one C-C triple bond is present. 110
 The general formula: is CnH2n-2 where n = 2,3,4,…
CH C CH2 CH3 CH3 C C CH3

1-butyne 2-butyne

Aromatic Hydrocarbons Chem
 Aromatic compound: contain one or more 110
benzene ring
H H
H C H H C H
C C C C
C C C C
H H H C H
C
H H

Aromatic Hydrocarbons Nomenclature Chem
 If one H atom has been replaced by another atom 110
or a group of atom →
the name of the atom or group then benzene
ethylbenzene aminobenzene (aniline)

CH2CH3 NH2
Cl NO2
chlorobenzene nitrobenzene
 If more than one substituent is present →
Chem
we must indicate the location of the second group
relative to first then benzene
110
Br
1
6 2 Br
Br
5 3
4 1,2-dibromobenzene Br
1,2 ortho o- (o-dibromobenzene)
1,3 meta m-
1,4 para p- Br
Br
1,4-dibromobenzene
1,3-dibromobenzene
(p-dibromobenzene)
(m-dibromobenzene)
Chem
1 NO2 110
6 2
5 3
4 Br
3-bromonitrobenzene
(m-bromonitrobenzene)

Q: Which one of these formulas is that of an unsaturated
hydrocarbon?
Chem
A. CH3 – CH2 – CH3 110
B. CH3 – CH = CH2
C. CH3 – CH2 – OH
Answer: B
Q: Which of the following is the general formula for alkynes?

A. CnH2n+2
B. CnH2n
D. CnH2n-2
Answer: C

Q: Which of these is the systematic Chem
name for the compound represented below? 110
CH3 – CH2 – CH – CH3

CH = CH2

A. 2-ethylbutane
B. 3-methyl-1-hexene
C. 3-methyl-1-pentene
Answer: C

24.4 Chemistry of Functional Groups Chem
• Functional Groups
110
Groups that are responsible for most of the
reactions of the parent compounds.
 Different Functional Groups forms:

Alcohol Ethers
Aldehyde Ketones
Carboxylic acid Esters Amines
Amino acid

Alcohols: contain the hydroxyl functional Chem
group and have the general formula R-OH. 110

Ethers: have the general formula R-O-R’. Chem
110
CH3OCH3
Dimethyl ether
C2H5OC2H5
Diethyl ether

Aldehydes and Ketones: Contain the
Carbonyl functional group Chem
C=O 110
R
 Aldehyde: has the general formula: C=O
H
 Ketone: has the general formula: R
C=O
R’
O O O
H C H H C CH3 H 3C C CH3
formaldehyde acetaldehyde acetone
Carboxylic acids: contain the carboxyl Chem
( -COOH ) functional group. 110
43
Esters: have the general formula R’COOR, Chem
where R is a hydrocarbon group, and R’ can 110
be H or a hydrocarbon
O
CH3COOH + HOCH2CH3 CH3 C O CH2CH3 + H2O
ethyl acetate
•The odour of fruits is due to the ester compounds they contain.

Amines: are organic bases with the general Chem
formula R3N. 110
CH3NH2 CH3CH2NH2
Methyl amine Ethyl amine

25.3 Proteins Chem
 Polymers: are large molecules made up of 110
repeating units called Monomers.
 Proteins: are polymers of amino acids. Termed
polypeptides
 Play a key role in nearly all biological processes
 Enzymes, the catalysts of biochemical reactions
 Transport of materials
 Storage of vital substances
 Coordinated motion
 Mechanical support
 Protection against diseases.
 Proteins high molar mass; ranging from about 5000 g.

Chem
110

25.3 Proteins Chem
 The basic structural unit of protein is amino 110
acids
 Amino acids: are the basic structural units of
proteins.
 Contain at least one amino group (-NH2)
 And at least one carboxyl group (-COOH)
H
O
Amino acid H C C
NH2 OH

Amino acids: existing form is pH dependent Chem
110

Amino acids: are joined in a protein by the formation of a
peptide bond
Chem
110
H O H O
+
H3N C C O- + +H3N C C O-
R1 R2
Peptide (amide) bond

planar
H O H O
+
H3N C C N C C O- + H2O
R1 H R2

Q: A protein is: Chem
A) a polymer of amino acids 110
B) a fatty acid ester of glycerol
C) a polysaccharide
D) an addition polymer
E) a polymer of fatty acids

(a)
(a) CH
CH3 3 OO CH CH3 3 (Ether)
CH2 2 CH (Ether)
Q: Classify each of the Chem
following molecules (b) CH
(b) CH3 3 CH
CH2 2 NH
NH2 2 (Amine)
(Amine) 110
as: OO
(c)
(c) CH (Aldehyde)
alcohol, aldehyde, CH3 3 CH
CH2 2 CC H (Aldehyde)
H
ketone, carboxylic acid,
ether, or amino acid (d)
(d) CH
CH3 3 CC CH CH3 3 (Ketone)
CH2 2 CH (Ketone)
OO
OO
(e) (Carboxylic
(e) HH CC OH
OH (CarboxylicAcid)
Acid)
(f)
(f) CH
CH3 3 CH
CH2CH2
2CH2 OH (Alcohol)
OH (Alcohol)
NH
NH2 2 OO
(g) (Amino
(g) CH
CH2 2 CC CC OH OH (AminoAcid)
Acid)
HH

Q: The formula Q: Which of the Chem
following is a 110
CH3CH2CH2CH2CH 2CH2CH2 OH
ketone?
represents:
A. CH3CH2COCH3
A. an alcohol
B. CH3CH2CHO
B. an alkene
C. an alkyne C. CH3OCH3
D. an unsaturated D. CH3CH2COOH
hydrocarbon E. H2C=C=CH2

Q: Which type of Q: Vanillin is used as a Chem
functional group does flavoring agent. 110
not include a carbonyl Identify the functional
group in its structure? group circled.
A. carboxylic acid
B. ether
C. ketone
A. aldehyde
D. aldehyde
B. ketone
E. ester
C. carboxylic acid
D. Alcohol
Chemistry 110
Dr. Laila Alharbi development
Dr. Nuha Wazzan
Dr. Eman Hegazy
Dr. Dalal Alezi
Dr. Nada Tashkandi
team
Dr. Amal Basaleh Dr. Effat Bahaidarah
Dr. Zahra Al-amshany Dr. Wafa Bawazeer
Dr. Nazeeha Alkayal Dr. Wejdan Alsaggaf
Dr. Nahed Bawakid Dr. Basma Alhogbi
Dr. Taghreed Fagieh Dr. Heba Alnajjar
Dr. Fatmah Alshareef Dr. Soha Albukhari
Dr. Qana Alsulami Dr. Zoya Zaheer
Dr. Heba Kashmery Dr. Amna Nisar Khan copyright of chemistry 110 development team 55

Chem110: Chapters 24, 25 Organic Chemistry

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Chem110

copyright of chemistry 110 development team 1

• Classify the organic compounds

• Differentiate between Aliphatic and Aromatic

• Naming different organic compounds

• Know the chemistry of functional groups

• Know the Proteins

copyright of chemistry 110 development team 3

• Hydrocarbons: compounds made of carbon and hydrogen only.

• Aliphatic Hydrocarbons: Do not contain benzene group.

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• Cycloalkanes: alkanes whose carbon atoms are joined in

• Alkenes: contain at least one carbon-carbon double bond,

• Alkynes: contain at least one carbon-carbon triple bond,

Alkane Only single covalent bonds are CnH2n+2

Cycloalkanes The carbon atoms are joined in CnH2n

Alkenes contain at least one C-C double CnH2n

Alkynes contain at least one C-C triple CnH2n-2

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CH4 C2H6 C3H8

methane ethane propane

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Q: A molecule with the formula C3H8 is a(n):

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1. Choose the longest chain in alkane

CH3 CH2 CH2 CH CH2 CH2 CH3

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CH3 CH CH2 CH2 CH3

CH3 CH2 CH2 CH CH3

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CH3 CH CH CH2 CH2 CH3

CH3 CH C CH2 CH2 CH3

CH3 CH CH2 CH2 CH CH3

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CH2 CH2 CH CH3

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Q: What is the structure of 2-propyl-4-methylhexane?

CH3 CH CH2 CH CH2 CH3

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2 chain isomers 2 Functional gp isomers

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CH2 CH CH2 CH3 CH3 CH CH CH3

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CH3 CH C CH2 CH2 CH2 CH3

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CH3CH=CH2 CH3CH=CHCH2CH3 CH3CH=CHCH3

(1) (2) (3)

• all three only 3

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(c) 4-ethyl- trans -2-heptene

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CH C CH2 CH3 CH3 C C CH3

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the name of the atom or group then benzene

ethylbenzene aminobenzene (aniline)