Revision of Organic

REVISION OF ORGANIC

SKILLS TO BE TESTED
• NOMENCLATURE AND CLASSIFICATION OF COMPOUND
• PHYSICAL PROPERTIES
• TYPES OF REACTIONS
• REACTION MECHANISM
• REAGENTS USED
• PREDICTING PRODUCTS
• ANALYSIS OF REACTIONS
• SYNTHESIS
• CHEMICAL TEST FOR A PARTICULAR FUNCTIONAL GROUP
NOMENCLATURE AND CLASSIFICATION
ORGANIC COMPOUND
NOMENCLATURE
• Check on the functional group to find the parent’s name
• Identify the priority of parents when more than one functional group is present
• Set numbering and name substituent
CLASSIFICATION :
 Classification of alkyl halides and alcohols is based on the class of C at which
OH or X is bonded
 Classification of amine and amide is based number of alkyl bonded to N.
PHYSICAL PROPERTIES
MELTING POINT
• Check on types of compound: ionic OR polar OR non-polar
compounds
• Consider the arrangement of atoms/molecules and the types of forces
involved
• Melting involves the process of solid ruptures, thus energy is used to
overcome forces in the SOLID lattice and allows molecules to move
freely IN LIQUID but with intermolecular forces acting between them
PHYSICAL PROPERTIES
BOILING POINT
• BOILING involves the change of liquid to gaseous, thus energy is used to
overcome forces in the liquid molecules and finally molecules are to move
freely without forces acting between them.
• Check on types of compound: ionic OR polar OR non-polar compounds
• Consider types of forces involved in liquids
• If the same type of forces are involved, consider molar mass or its molecular
structure
• Compare the strength of forces and deduce which has higher boiling points
PHYSICAL PROPERTIES
SOLUBILITY
• Ability to dissolve in a solvent.
• Check polarity and type of forces; only the like dissolves the like
• Polar molecules dissolve in polar solvents such as water.
• The ability to form a hydrogen bond with water molecules allows the
substance to dissolve in aqueous
• Non-polar molecules dissolve in non-polar solvents because they have
the same type of interaction or forces acting between molecules.
ACIDITY
• Recall definition of acid and base (Bronsted-Lowry and Lewis)
• Compare the acidity of alcohol, phenol and carboxylic acid.
• Understand the factors influence the acidity – resonance effect (stability of
ion formed) and inductive effect (the presence of EWG and EDG)
TABLE 2 shows the boiling points and solubilities of pentane, 1-butanol,
methyl ethanoate and propanoic acid.

Compound Molecular Boiling point, Solubility in water,

mass oC g/100g
Pentane 72 36 0.04
1-Butanol 74 117 8.3
Methyl ethanoate 74 57 24.4
Propanoic acid 74 141

1. Explain why propanoic acid has the highest boiling point and most
soluble?
2. Explain why the boiling point of 1-butanol is higher than that of

methyl ethanoate whereas the solubility is the reverse?
[5 marks]
Arrange the following alkanes in order of decreasing boiling point. Explain
your answer.
2,2-dimethylbutane, hexane, butane

[3 marks]
Arrange the following alkanes in order of increasing boiling points. Explain
your answer.
2,2-dimethylheptane, 4-ethylheptane, 2,2,4,4-tetramethylpentane, nonane
[4 marks]
Acidity
Arrange acetic acid, ethanol and phenol in order of increasing acidity. Explain
in terms of the stability of their conjugate bases.
[4 marks]
Arrange the following compounds in descending order of acidity. Explain your
answer.
phenol, cyclohexanol, benzoic acid, 4-nitrophenol
[5 marks]
Arrange the following compounds in ascending order of acidity. Explain your answer.
2,3-dichlorobutanoic acid, 1-butanol, butanoic acid, 4-chlorobutanoic acid,
2-chlorobutanoic acid
[5 marks]
Types of reaction
• Molecules with a particular functional group undergo a specific type
of reaction
• Types of reaction leads to the mechanism
• Should be able to identify types of reaction and give reason for such
reaction
• Example:
Why does benzene undergo electrophilic aromatic substitution?
TYPES OF REACTION
 Alkane – Free radical substitution
 Alkene – Electrophilic Addition
 Benzene – Electrophilic Aromatic Substitution
 Alkyl halides – Nucleophilic substitution (SN1 , SN 2) & Elimination
 Alcohols – (a) as nucleophiles
(b) nucleophilic substitution & Elimination
(d) oxidation for 1o and 2o alcohols
 Carbonyls – Nucleophilic addition
 Carboxylic acids – Nucleophilic substitution at acyl
ANALYSIS OF COMPOUNDS
• Questions are given in paragraphs.

• Read each line carefully. Deduce the characters ( isomers, optically
active or other properties, such as acidic, basic, etc…)
• Transform the sentences to schematic pathways.
• Begin with the end that gives the most information/clues
• Deduce the structural formulas based on the formulas and correct
functional groups.
TIPS on Deducing formulas
If the formulas has the following characters
• a ratio of C:H is almost 1:1; probably it’s a benzene ring

• contains an O atom ; probably an alcohol or carbonyl
• contains two O or more: probably a carboxylic acids, esters or a diol
• Contains one N atom; probably an amine
• Contains N and O ; probably an amide or hydroxyl and amine
EXAMPLE
W, X and Y are isomers with a molecular formula of C7H7Br. When W, X and
Y are subjected to oxidation by hot acidified KMnO4, only Y gives benzoic
acid. The oxidation too causes W and X to form compounds P and Q with the
molecular formula of C7H5O2Br. Determine the structural formulas of W, X,
Y, P and Q.
SOLUTION
• TIPS:
Ratio of C:H is almost 1:1, thus it
may contain phenyl/benzene ring,
Consider the formula C7H7Br. that is the C6H5
Compounds probably have the structure of a

disubstituted benzene OR a benzyl halide.
Suggest your isomeric structure.

Then, test the structure by writing the
equations/schematic pathway that fits your structure
Deduce the structural formulas of W, X, Y, P and Q.
Exercise 1
• An alkyl bromide A reacts with CH3CH2OH to give B , whereas compound
CH3COOCH(CH3)CH2CH3 is formed when A is treated with a nucleophile.
Dehydrohalogenation of A produces C which obeys Saytzeff's rule. Deduce
the structures of A, B , C and nucleophile.
(6 marks)
Trend of questions
Questions given in form of paragraph. In one paragraph for a particular
number of question, it comprises the several questions. It might contain:
 writing the chemical reaction equations,
 state the type of reaction and
 suggest the mechanism for certain reaction.
*Read carefully and underline/highlight the questions
Exercise 2
Compound BB is formed from the reaction of benzene with CH3CH2Cl in the
presence of AlCl3. Oxidation of BB with hot acidified solution of KMnO4
gives CC . Treatment of CC with ethanol in the presence of traces of sulphuric
acid produces DD.
Suggest the structures of BB , CC and DD. Write mechanism for the
formation of BB .
[6 marks]
Exercise 3
Acid catalyzed dehydration of 2-pentanol gives compound V and W.
Compound V exhibits geometrical isomerism. Ozonolysis of compound V
produces Z and AA. Identify the major product of acid catalyzed dehydration
and explain your answer. Write the mechanism for the formation of
carbocation in dehydration of 2-pentanol. Write reaction equation for the
ozonolysis of V.
[5 marks]
SYNTHESIS QUESTIONS
Require the following skills:
• Remember reagents and conditions required
• Able to draw initial and final structures correctly
• Analyse the number of carbon in initial and final
 additional carbon – you may use Grignard reagent OR nitrile compound
 reduce carbon – use Hoffman degradation ,…..
• Know what can be done to the functional group
• Able to think forward and reverse. Some solution is easily deduced from the
final product rather the initial compound
REAGENT USED
• To be very careful about whether the reagent used is a mixture of a

whole or added stepwise.
• Condition is important too
• Knowing the reagents is the basic step to SYNTHESIS
Indicate the reagents needed for the following
conversions:
i. butanone to 2-butanol
ii. butanone to 2-hydroxy-2-cyanobutane
iii. benzene to acetophenone
Given the following alcohols:
• Show how you would prepare alcohol G via a Grignard reagent.

Show how 1-cyclohexylpropanone can be synthesized from
an alkyl halide containing nine carbon atoms.
Show how compound W can be prepared from
benzene. Give all reagents and intermediates formed.
CH3
C CN
CH3
Compound W
Suggest suitable reagents for the conversion of butanal to
the following compounds:
• 1-butanol
• butanoic acid
Show the synthetic steps for the preparation of
isopropylcyclopentane from propanone via Grignard reagent.
• Aniline is one of the important starting materials in the chemical
industry. Starting from benzene, show how aniline can be
prepared.
One of the industrial applications of aniline is in the production
of azo compound. Write the synthetic pathway for the
formation of azo compound from aniline.
CHEMICAL TEST
• Target - to distinguish two classes of compounds by using one
common test
• Suggest a chemical test by giving the correct test reagents used.
• State the observation. One compound should give a result that is
contradict to the other.
• If no reaction occurs, observation should be stated as ‘No Observable
Change’
• Write chemical equation that reflects the observation stated for a
positive result.
The table below may help you to present your
answer completely.
Exercise :
Suggest a chemical test to differentiate the
following pairs:
a. 2-butene and butane h. Ethanamine and aniline
b. Butanone and 1-butanol i. 2-pentanone and 3-pentanone
c. Toluene and benzene j. 1-propanamine and N-methylehanamine
d. 2-pentanone and 3-pentanol k. N,N-dimethylaniline and N-methylaniline
e. Benzaldehyde and pentanal
f. Butanal and butanone
g. Phenol and cyclohexanol

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REVISION OF ORGANIC

Compound Molecular Boiling point, Solubility in water,

1-Butanol 74 117 8.3

Methyl ethanoate 74 57 24.4

Propanoic acid 74 141

2. Explain why the boiling point of 1-butanol is higher than that of

2,2-dimethylbutane, hexane, butane

• Questions are given in paragraphs.

• a ratio of C:H is almost 1:1; probably it’s a benzene ring

Compounds probably have the structure of a

Suggest your isomeric structure.

• To be very careful about whether the reagent used is a mixture of a

• Show how you would prepare alcohol G via a Grignard reagent.

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