ORGANIC CHEMISTRY

OCHE120150E

VÕ THỊ NGÀ, PhD.

ngavt@hcmute.edu.vn
Department: Chemical Technology
Faculty: Chemical and Food Technology
 CHAPTER 1
MOLECULAR REPRESENTATIONS
IUPAC NOMENCLATURE
REACTION CLASSIFICATION

2
 GOALS

Course Description Learning

Learning At the end of the course, students are able to Outcomes
outcomes

Recognize, name, and represent organic ELO1

CO1 compounds and organic functional groups

3
 CONTENT

1. Molecular representations

2. Organic compound nomenclature

2.1. IUPAC rules
2.2. Nomenclature of the organic compounds

3. Organic reaction classification

3.1. Classification based on reaction result
3.2. Classification based on reagents
3.3. Classification based on oxidation state

4
 Task at home before class

 Watch the following video clips:

 IUPAC Nomenclature of Alkanes: Part 1
 https://www.youtube.com/watch?v=rHyIdxOzj9U&index=2&list=PLybg94GvOJ9
GtvOUYLW601u1Oiaoat2UF&t=0s
 IUPAC Nomenclature of Alkanes: Part 2
 https://www.youtube.com/watch?v=hC1LQmRsvSQ&index=2&list=PLybg94GvO
J9GtvOUYLW601u1Oiaoat2UF
 IUPAC Nomenclature of Alkenes and Alkynes
 https://www.youtube.com/watch?v=nWI4Itkg7PU&list=PLybg94GvOJ9GtvOUYL
W601u1Oiaoat2UF&index=4
 IUPAC Nomenclature of Cyclic Compounds
 https://www.youtube.com/watch?v=B02E4REukXE&index=5&list=PLybg94GvOJ
9GtvOUYLW601u1Oiaoat2UF
 IUPAC Nomenclature of Haloalkanes and Alcohols
 https://www.youtube.com/watch?v=KSi3_q7XXTk&index=3&list=PLybg94GvOJ9
GtvOUYLW601u1Oiaoat2UF

5
 Task at home after class

 Watch the following video clips:

 Practice Problem: IUPAC Nomenclature Examples

 https://www.youtube.com/watch?
v=ATZOivOGwbw&list=PLybg94GvOJ9Hkihn7mQnLBl2YJKbU1cjO&index=3

 Read Skill builder reviews and Do problems in the file “Chapter

1- Homework”

6
 Molecular Representations

Lewis structure Bond-line structure

Single bond Double bond Triple bond

Melissa :Organic Chemistry Introduction Part 1 – Structure
https://www.youtube.com/watch?v=HRz-jH4CAy8&list=PLytGGifnD9dV1oDvifUDGqEU2VmKUUhd1&index=1 7
 Practice
1. Draw bond-line representations for the following Lewis
structures
H HH HH HH
H H H H C H H H C C
Cl C C C C C C C H H
C C C C C C
H H H H C C H O H
H
H HH H H H

2. Draw bond-line representations for 3 possible isomers

given the formula: C5H9ClO

2-8
Identifying functional groups

When certain atoms are

bonded together in
specific arrangements,
they undergo specific
chemical reactions
 Functional group

Melissa :Organic Chemistry Introduction Part 2

– Functional group
https://www.youtube.com/watch?
v=0R2phZMxYSI&list=PLytGGifnD9dV1oDvifU
DGqEU2VmKUUhd1&index=2

9
Identifying functional groups (cont.)

10
Identifying functional groups (cont.)

11
 ORGANIC COMPOUND NOMENCLATURE
RULES Melissa: 3 Steps for Naming Alkanes | Organic Chemistry
https://www.youtube.com/watch?
v=QzDli_Llo9A&list=PLytGGifnD9dV1oDvifUDGqEU2VmKU
Uhd1&index=3

PREFIX PARENT CHAIN SUFFIX

Unsaturated level Functional group

CH2COOH
HCCH2CHCHCH2CHCH3
O OH Br
6-bromo-4-hydroxy-3-(2-oxoethyl)heptanoic acid
12
 Table 2.1. Nomenclature of prefixes and suffixes
listed from highest to lowest priority
Thứ tự
Highest
Loại hợp Structure
Compound chất Tiếp đầu ngữ
Prefix Tiếp vĩ ngữ
Suffix
priority
ưu tiên
Carboxylic acid RCOOH Carboxy -oic acid
Ester RCOOR’ Alkoxycarbonyl -oate
Amide RCONHR’ Amido -amide
Nitrile RCN Cyano -nitrile
Aldehyde RCH=O Oxo (=O) -al
Aldehyde RCH=O Formyl (-CH=O) -al
Ketone R,R’>C=O Oxo (=O) -one
Alcohol R-OH Hydroxy -ol
Amine R-NH2 Amino -amine
Alkene RCH=CHR’ Alkenyl -ene
Alkyne RCCR’ Alkynyl -yne
Alkane RCH2-CH2R’ Alkyl (*) -ane

Lowest
Ether R-O-R’ Alkoxy (*) -
priority Alkyl halide R-X Halo (*) -
(*) Equivalent priority 13
 NOMENCLATURE
IUPAC Rules
Parent chain: the way to identify
The longest consecutive chain of carbons with the highest
priority functional group.

CH2COOH
HCCH2CHCHCH2CHCH3
O OH Br

6-bromo-4-hydroxy-3-(2-oxoethyl)heptanoic acid
14
 The parent chain is the longest chain carring the highest
priority group and maximum functional groups.
The priority:
- Cyclic system
- maximum multiple bonds (triple bond  or double bond=)
- maximum double bond =
- maximum substituents.
Cl CH2CH3 Br

CH2CH3 H CH3CHCHCHCH2CHCH3
C CH2 OH
CH3CHCHCH2CHCH3
CH3CH2CHCHCH2CHCH3
OH Br
OH Br 15
 NOMENCLATURE
Rules
Parent chain: the way to number
Number the parent chain in the direction such that the
position number of the highest priority group is the
smaller number
2 1
CH2COOH
3 4 5 6 7
HCCH2CHCHCH2CHCH3
O OH Br

6-bromo-4-hydroxy-3-(2-oxoethyl)heptanoic acid
16
 NOMENCLATURE
Rules
Parent chain: the way to number

When the highest priority group is absent, number in the

direction such that :
- The total of locants is the smallest.

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 NOMENCLATURE
Rules
Parent chain: the way to name
The root name is named for the carbon number of the
parent chain.
2 1
CH2COOH
3 4 5 6 7
HCCH2CHCHCH2CHCH3
O OH Br

6-bromo-4-hydroxy-3-(2-oxoethyl)heptanoic acid
18
 Table 2.2.
Nomenclature of linear alkanes with 1 to 100 carbons
No. of carbons No. of carbons No. of carbons
Số carbon Name
Tên Số carbon Name
Tên Số carbon Name
Tên
1 Methane 11 Undecane 21 Henicosane
2 Ethane 12 Dodecane 22 Docosane
3 Propane 13 Tridecane 23 Tricosane
4 Butane 14 Tetradecane 24 Tetracosane
5 Pentane 15 Pentadecane 30 Triacotane
6 Hexane 16 Hexadecane 31 Hentriacontane
7 Heptane 17 Heptadecane 32 Dotriacontane
8 Octane 18 Octadecane 40 Tetracontane
9 Nonane 19 Nonadecane 50 Pentacontane
10 Decane 20 Icosane 100 Hectane

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NOMENCLATURE
Rules
Suffix for the unsaturated level
Unsaturation Type of
suffix
level bond
0 Single bond -ane
1 Double bond -ene
2 Triple bond -yne

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 NOMENCLATURE
Rules
Suffix for the highest priority group

Refer the Table 2.1

2 1
CH2COOH
3 4 5 6 7
HCCH2CHCHCH2CHCH3
O OH Br

6-bromo-4-hydroxy-3-(2-oxoethyl)heptanoic acid
21
 NOMENCLATURE
Rules
Prefix
 Indicate all substituents with the prefixes refered in Table
2.1.
 Place the prefixes, with appropriate position numbers, in
alphabetical order before the root name.
2 1
CH2COOH
3 4 5 6 7
HCCH2CHCHCH2CHCH3
O OH Br
6-bromo-4-hydroxy-3-(2-oxoethyl)heptanoic acid
22
 Prefixes of some alkyl types
1
CH3 CH2 CH2 CH2 CH2 CH3 CH3 CH2 CH2 CH2 CH2 CH2
n-hexane n-hexyl 1
CH3 CH CH2 CH2 CH3 CH3 CH CH2 CH2 CH2
CH3 CH3
isohexane isohexyl
CH3 CH3 1
CH3 C CH2 CH3 CH3 C CH2 CH2
CH3 CH3
neohexane neohexyl
CH3
1 1
CH3 CH2 CH2 CH2 CH CH3 CH2 CH2 C
CH3 CH3
sec-hexyl tert-hexyl 23
 NOMENCLATURE
Nomenclature of hydrocarbon
Dave: IUPAC Nomenclature of Alkanes: Part 1
https://www.youtube.com/watch?v=rHyIdxOzj9U
&index=2&list=PLybg94GvOJ9GtvOUYLW601u1
Naming Alkanes Summary Oiaoat2UF&t=0s
 2. Nomenclature
Dave: IUPAC Nomenclature of Alkanes: Part 2
https://www.youtube.com/watch?v=hC1LQmRsvSQ&ind
ex=2&list=PLybg94GvOJ9GtvOUYLW601u1Oiaoat2UF
2.2. Nomenclature of hydrocarbon
Dave: IUPAC Nomenclature of Alkenes and Alkynes
Hydrocarbon https://www.youtube.com/watch?v=nWI4Itkg7PU&list=PLy
bg94GvOJ9GtvOUYLW601u1Oiaoat2UF&index=4

Melissa: Drawing Alkanes When Given the Structure Name

https://www.youtube.com/watch?
v=iTo2n4ayiJU&list=PLytGGifnD9dV1oDvifUDGqEU2VmK 25
 Nomenclature
Nomenclature of hydrocarbon
Cyclic hydrocarbon :

Dave: IUPAC Nomenclature of Cyclic Compounds

https://www.youtube.com/watch?v=B02E4REukXE&index=5&list=PLybg94GvOJ9GtvOUYLW601u1Oiaoat2UF 26
 Nomenclature
Nomenclature of hydrocarbon
Aromatic hydrocarbon : monosubstituted derivatives of benzene

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 Nomenclature
Nomenclature of hydrocarbon
Aromatic hydrocarbon :
Disubstituted derivatives of benzene
Isomers differing from each other in the relative positions of two
substituents can be named in two ways:
(1) using the descriptors ortho, meta, and para or
(2) using locants (i.e.,1,3 is the same as meta)

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 NOMENCLATURE
Nomenclature of hydrocarbon
Aromatic hydrocarbon :
Di/trisubstituted derivatives, whose parents have common names

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 NOMENCLATURE
Nomenclature of hydrocarbon
Aromatic hydrocarbon :
Polysubstituted derivatives of benzene

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 NOMENCLATURE
Nomenclature for mono or poly-functional compounds

Halogen derivatives:
Common name: alkyl halide

IUPAC name: haloalkane

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 NOMENCLATURE
Nomenclature for mono or poly-functional compounds

Ether
Common name: alkyl ether

Dave: IUPAC Nomenclature of Haloalkanes and Alcohols

https://www.youtube.com/watch?v=KSi3_q7XXTk&index=3&list=PLybg94GvOJ9GtvOUYLW601u1Oiaoat2UF 32
 NOMENCLATURE
Nomenclature for mono or poly-functional compounds
Ether
Name of RO- : alkyl  alkoxy

IUPAC name: alkoxyalkane

33
 NOMENCLATURE
Nomenclature for mono or poly-functional compounds

Alcohol
Common name: alkyl alcohol

34
 2. NOMENCLATURE
2.3. Nomenclature for mono or poly-functional compounds

2.3.2.2. Alcohol
IUPAC name:

Br OCH3
CH3CH2CHCH2CHO CH3CHCHCH2COOH CH3CHCHCH2COOH

OH OH OH
3-hydroxypentanal 4-bromo-3-hydroxypentanoic acid 3-hydroxy-4-methoxypentanoic acid
Dave: Practice Problem: IUPAC Nomenclature Examples
https://www.youtube.com/watch?v=ATZOivOGwbw&list=PLybg94GvOJ9Hkihn7mQnLBl2YJKbU1cjO&index=3 35
 2. NOMENCLATURE
2.3. Nomenclature for mono or poly-functional compounds

2.3.3. Amine
Common name: alkylamine

36
 NOMENCLATURE
Nomenclature for mono or poly-functional compounds

Amine
IUPAC name:

Br OH
CH3CH2CHCH2CHO CH3CHCHCH2COOH CH3CHCHCH2COOH

NH2 NH2 NH2

3-aminopentanal 3-amino-4-bromopentanoic acid 3-amino-4-hydroxypentanoic acid

37
 NOMENCLATURE
Nomenclature for mono or poly-functional compounds

Aldehyde
Common name: ic acid  aldehyde

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 NOMENCLATURE
Nomenclature for mono or poly-functional compounds

Aldehyde
IUPAC name:

CHO
COOH COOH
OHC H3C

8-oxooctanoic acid 5-formyloctanoic acid

OHC CHO OHC CHO

heptanedial 2,6-dimethylheptanedial
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 NOMENCLATURE
Nomenclature for mono or poly-functional compounds

Ketone
Common name: alkyl ketone, ic acid  ophenone
IUPAC name:

40
 NOMENCLATURE
Nomenclature for mono or poly-functional compounds

Carboxylic acid
Common name: from origin

41
 NOMENCLATURE
Nomenclature for mono or poly-functional compounds

Carboxylic acid
IUPAC name:

HOOC COOH HOOC COOH

heptanedioic acid 2,6-dimethylheptanedioic acid

42
NOMENCLATURE
Nomenclature for mono or poly-functional compounds

Ester
alkyl ---------ate

43
NOMENCLATURE
Nomenclature for mono or poly-functional compounds

Acyl halide
---ic acid  ---yl halide
Carboxylic acid  carbonyl halide

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NOMENCLATURE
Nomenclature for mono or poly-functional compounds

Acid anhydride
Carboxylic anhydride

45
 NOMENCLATURE
Nomenclature for mono or poly-functional compounds

Amide
ic acid / oic acid  amide
carboxylic acid  carboxamide

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Common names

halide
ether

Alkyl alcohol
-amine
ketone
47
Writing equations for organic reactions

One reaction

48
Rules for writing organic reactions

Two or more sequential reactions

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 CLASSIFICATION OF ORGANIC REACTION
Classification based on reaction result
Addition reaction, A

Substitution reaction, S
Y = H or a heteroatom

Elimination reaction, E

50
CLASSIFICATION OF ORGANIC REACTION
Classification based on reaction result
A

51
 CLASSIFICATION OF ORGANIC REACTION
Classification based on reaction reagent
Electrophile – Nucleophile –
electrophilic reagent, E: nucleophilic reagent, N:
positively charged or neutral all molecules or ions with a
species having vacant free pair of electrons or at
orbitals that are attracted least one pi bond that donates
to an electron rich centre an electron pair to an
elctrophile
cation - neutral
positively species having Neutral species
anion having an electron
charged vacant orbitals
carbanion, OH-, pair
carbocation, SO3, AlCl3, FeCl3,
RO-, RCC-, X-, H O, ROH, NH ,
H3O+, NO2+, BF3, CO2,… 2 3
CN-, CH3COO-
SO3H+ RNH2,…
52
 CLASSIFICATION OF ORGANIC REACTION
Classification based on both reaction reagent and result

 Electrophilic addition reaction (AE),

 Nucleophilic addition reaction (AN),

 Electrophilic substitution reaction

(SE),

 Nucleophilic substitution reaction

(SN), 53
 CLASSIFICATION OF ORGANIC REACTION
Classification based on oxidation state
Reduction Oxidation
• Gain of electrons • Loss of electrons
• Formation of C-H bonds • Loss of C-H bonds
• Loss of C-O bonds (or • Formation of C-O bonds
its equivalent) (or its equivalent, such
as C-N, C-Cl,…)
Oxidation

Reduction 54
 CLASSIFICATION OF ORGANIC REACTION
Classification based on oxidation state

Reduction reaction

Oxidation reaction

Reduction reaction
Oxidation reaction

Reduction reaction
Oxidation reaction 55