EXTRA EXERCISE MODULE CHAPTER 5 2020/2021
CHAPTER 5 : ALCOHOLS
WORKSHEET 5.1
For each alcohol write the IUPAC name and state the class of alcohol.
1. CH3CH2CH2CH2OH = _________________________
2. CH3CH(CH3)CH2OH = __________________________
3. CH3CH(OH)CH2Cl = _________________________
4. HOCH2CH2CH2OH = _________________________
5. CH3CH(OH)CH2CH2CH3 = ________________________
6. (CH3)3COH = _____________________________
7. CH3
CHCHCH2CH2OH
CH2CH3
__________________________________
8.
CH3
OH
__________________________________
9. CH2 CHCH2OH = ________________________
10. OH
H3C
______________________________
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EXTRA EXERCISE MODULE CHAPTER 5 2020/2021
WORKSHEET 5.2 2. Isopropyl alcohol
Draw the structure formulae for the following name.
1. 2-hexanol
3. 5-methyl-2-hexanol 4. 4-chloro-3-methyl-1-butanol
5. 2-bromo-5 methylcyclopentanol 6. 1,4-cyclohexanediol
7. 1,2,3-pentanetriol 8. 2-chlorophenol
9. 1-chloro-5,5-dimethyl-2-hexanol 10. Cis-3-pentene-1-ol
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EXTRA EXERCISE MODULE CHAPTER 5 2020/2021
WORKSHEET 5.3
BOILING POINT
1. Predict which of the compound in each of the following pairs is higher boiling point. Briefly
explain your answer.
a) CH3CH2OH and CH3CH2CH2OH
Answer :
b) CH3CH2CH2CH2OH and CH3CH2CH2CH2CH2CH2OH
Answer :
c) Ethanol and pentane
Answer :
d) 1-butanol and 1,3-prapanediol
Answer :
2. Predict which of the compound in each of the following pairs is more soluble in water. Briefly
explain your answer.
i) Butane and 1-butanol
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EXTRA EXERCISE MODULE CHAPTER 5 2020/2021
ii) 1-butanol and 1,4-butanediol
iii) 1-propanol and 1-pentanol
WORKSHEET 5.4
Preparation of alcohol
Complete the following equations.
i) Fermentation
yeast
C6H12O6
ii) Hydration of alkenes
a) H2C CH2 + H2O H+
b) CH3 H+
+ H2O
c) CH3CH2CH CH2 + H2O H+
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EXTRA EXERCISE MODULE CHAPTER 5 2020/2021
Reaction of alcohol
i) Reaction with Group 1 and Group 2 metal
a) CH3OH + Na
b) OH
+ Na
c)
HOCH2CH2CH2CH2OH + 2K
d) OH
CH3CCH3 + Mg
CH3
OH
+ Ca
CH3
ii) Oxidation with hot acidified KMnO4 or K2Cr2O7
Oxidation of 1o alcohol
CH3CH2CH2OH KMnO4/H+
CH3 KMnO4/H+
CH3CHCH2OH
CH2OH K2Cr2O7/H+
CH2OH K2Cr2O7/H+
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EXTRA EXERCISE MODULE CHAPTER 5 2020/2021
Oxidation of 2o alcohol
OH KMnO4/H+
CH3CCH3
H
CH3 K2Cr2O7/H+
CH3CHCHCH3
OH
Oxidation of 3o alcohol
Tertiary alcohols do not undergo ________________ under normal condition.
iii) Oxidation with PCC in CH2Cl2
Oxidation of 1o alcohol
CH3CH2CH2OH PCC/ CH2Cl2
iv) Esterification H+
O
CH3CH2OH + HC OH
O H+
CH3C OH + HO
O H+
HO CHCH3 + HC3CHC OH
CH3 CH3
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EXTRA EXERCISE MODULE CHAPTER 5 2020/2021
O H+
C OH
HO CH3 +
v) Dehydration of alcohol
CH3CH2CH2OH conc.H2SO4
OH
conc.H2SO4
OH
CH3CH2CHCH3 conc.H2SO4
CH3
OH conc.H2SO4
CH3
WORKSHEET 5.5
Chemical Test
i) Suggest a chemical test to distinguish the following pairs
a) 1- propanol and 2-methyl-2-propanol
Name of test :
Reagent :
Equation :
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EXTRA EXERCISE MODULE CHAPTER 5 2020/2021
Observation :
b) Ethanol and 1-butanol
Name of test :
Reagent :
Equation :
Observation :
WORKSHEET 5.6 2. What is the IUPAC name of the following
MULTIPLE CHOICE QUESTIONS
compound? CH3
1. What is the IUPAC name of the Br
following compound?
OH
CH3 55
CH3CHCHC(CH3)2
OH
EXTRA EXERCISE MODULE CHAPTER 5 2020/2021
A. 2-phenyl-1,4-dimethyl-3-pentanol A. 1-bromo-2-methylcyclohexanol
B. 4,4-dimethyl-2-phenyl-3-pentanol B. 4-bromo-3-methylcyclohexanol
C. 2,2-dimethyl-4-phenyl-3-pentanol C. 2-bromo-1-methylcyclohexanol
D. 1-tert-butyl-2-phenyl-1-propanol D. 4-bromo-5-methylcyclohexanol
E.
3. Which of the following are secondary 4. Arrange the following compounds in
alcohols? order of increasing boiling point.
I CH3CH2CH2OH
OH OH OH II (CH3)2CHOH
I II III III HOCH2CH2CH2OH
IV HOCH2CH2OH
A. I and II
B. I,II and III A. I < II < III < IV
C. I and III B. II < I < IV < III
D. II and III C. IV < III < II < I
D. I < II < IV < III
5. Which of the following compounds has
the highest boiling point? 6. Which of the following alcohols would
react fastest with Lucas reagent?
A. CH3CH2CH2CH2CH2OH
B. OH A. (CH3)3CCH2OH
B. (CH3)2CHCH2CH2OH
CH3CHCH2CH3 C. (CH3)2C(OH)CH2CH3
C. OH D. CH3CH2CH2CH(OH)CH3
CH3CCH3
OH
D. HOCH2CH2CH2OH
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EXTRA EXERCISE MODULE CHAPTER 5 2020/2021
7. Which of the following compounds 8. What is the best choice of reagent for the
does not decolourise acidified
potassium permanganate? following conversion?
A. ?
CH3
CH3CH2OH CH3CHO
B. OH
A. KMnO4/H+
B. NaOH
C. PCC/CH2Cl2
D. Conc. H2SO4
C. (CH3)2CHOH
D. (CH3)3COH
9. Which of the following alkenes is the 10. Arrange the compound in increasing
major dehydration product of 2,2- solubility in water.
dimethyl-1-bCuHta3nol?
1,3-propanediol, 1,2-ethanediol, n-butane, 1-
A. CH3CH2C CHCH3 propanol
B. CH2 C(CH2CH3)2
C. (CH3)2CHC(CH3) CH2 A. 1,3-propanediol <1,2-ethanediol < 1-
D. (CH3)2C C(CH3)2 propanol < n-butane
B. 1,2-ethanediol < 1-propanol < 1,3-
propanediol < n-butane
C. n-butane < 1-propanol < 1,3-propanediol
< 1,2-ethanediol
D. n-butane < 1,3-propanediol < 1-propanol
< 1,2-ethanediol
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EXTRA EXERCISE MODULE CHAPTER 5 2020/2021
WORKSHEET 5.7
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EXTRA EXERCISE MODULE CHAPTER 5 2020/2021
WORKSHEET 5.8 : SAMPLE PSPM
Session 2008/2009
1. D and E have the same molecular formula of C4H10O. Both evolved bubbles of gas when treated
with sodium metal. D gave a green solution with chromic acid whereas the colour of chromic acid
was unchanged with E.
i. Based on the above observation, state the functional groups of D and E.
ii. Draw the structures of D, E and the product formed when D reacts with chromic acid.
[5 marks]
Answer :
Session 2012/2013 DK 045
2. Based on the reaction below:
i. Draw the structure of N.
ii. Name the test used in the above reaction.
____________________________________
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EXTRA EXERCISE MODULE CHAPTER 5 2020/2021
iii. State your observation.
_____________________________________________________________
Session 2013/2014 DK 045 (MST)
3. Compound N,P,Q and R are isomers of alcohol with molecular formula C4H10O.P is
tertiary alcohol and gives cloudy solution with Lucas reagent,while Q gives positive iodoform
test.R has higher boiling point than N due to its larger surface area.
i. Draw the structure of N,P,Q and R
ii. State the observation for positive iodoform test.
______________________________________________________________________________
iii. Write the chemical equations for all reactions involved
[ 5 marks ]
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EXTRA EXERCISE MODULE CHAPTER 6 2020/2021
CHAPTER 6 : CARBONYL
WORKSHEET 6.1
For each alcohol write the correct IUPAC name.
1. H3C CH2 CH2 CH2 CH
O
________________________________
2.
Br CH3
H3C C CH2 CH C H
H2C CH3 O
________________________________
3. H O
________________________________
4. O
H
_________________________________
5. Br
OC
H NO2
_________________________________
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EXTRA EXERCISE MODULE CHAPTER 6 2020/2021
6. CH3 O
CH CH2 CH
H3C
_____________________________
7. CH3 O CH3
H3C CH C CH2 CH2 C Cl
CH3
_______________________________________
8. CH2
CH3 O
H3CH2C CH C
_________________________________________
9. O
Cl
CH2CH3
__________________________________________
10.
O
CH3CHCHCH2CH3
CH3
_______________________________________
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EXTRA EXERCISE MODULE CHAPTER 6 2020/2021
WORKSHEET 6.2 2. 2-methylpropanal
Draw the structure for the following IUPAC name.
1. propanal
3. Phenylmethanal @ benzaldehyde 4. 4-nitrobenzaldehyde
5. 2-pentanone 6. 4-methyl-2-pentanone
7. 1-phenyl-2-propanone 8. 1-cyclopentyl-2-butanone
9. acetophenone 10. 1-chloro-2-pentanone
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EXTRA EXERCISE MODULE CHAPTER 6 2020/2021
WORKSHEET 6.3
Preparation of carbonyl compound.
Complete the following reaction.
i) Oxidation of alcohol
1o alcohol
CH3
a) CH3CH2CHCH2OH PCC/CH2Cl2
)
b) CH2OH PCC/CH2Cl2
)
c) CH3
) CH3CHCH2CH2OH PCC/CH2Cl2
2o alcohol
OH
a) CH3CCH3 KMnO4/H+
)H
)b) OH KMnO4/H+
)
)
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EXTRA EXERCISE MODULE CHAPTER 6 2020/2021
WORKSHEET 6.4
Chemical Properties
i) Addition with KCN, H3O+ or NaCN, H3O+
O
KCN/H+
a) CH3CH2 C CH3
)
)b) NaCN/H+
CH3CH2CHO
)
) O NaCN/H+
c)
b) CH3CCH3
)
) d) CH3 O KCN/H+
b) CH3CHCH2C H
)
)
ii) Reduction to alcohol.
a) CH3CH2CHO i) LiAlH4
ii) H3O+
b)
)
b) ) O NaBH4 in methanol
CH3CH2CH2CH
)
c) ) O NaBH4 in methanol
CH3CH2CCH3
)
)
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EXTRA EXERCISE MODULE CHAPTER 6 2020/2021
d)
O H2/Pt
CH2CCH3
)
)
WORKSHEET 6.5
Chemical Test
i) Suggest a chemical test to distinguish the following pairs
a) 1- propanol and propanal
Name of test :
Reagent :
Equation :
Observation :
b) Methanal and ethanal
Name of test :
Reagent :
Equation :
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EXTRA EXERCISE MODULE CHAPTER 6 2020/2021
Observation :
c) Propanal and propanone
Name of test :
Reagent :
Equation :
Observation :
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EXTRA EXERCISE MODULE CHAPTER 6 2020/2021
WORKSHEET 6.6 2. What is the IUPAC name of the following
compound?
MULTIPLE CHOICE QUESTIONS
CH3 O
1. What is the IUPAC name of the following CH3
compound? A. 2-pentanone
O B. 3- pentanone
C. 5-hexanone
CH D. 2-hexanone
NO2 4. Which of the following groups can be
A. 4-nitrobenzaldehyde classified as carbonyl?
B. 2,4-dinitrobenzaldehyde
C. 1-nitroheptanal A. Carboxylic acids
D. Benzophenone B. Aldehyde and ketone
3. Which of the following alcohols can be C. Ester
oxidized to a ketone? D. Ether
A. CH3CH2OH 6. Which of the following pair of compounds can
B. CH3CH(OH)CH3 be distinguished by using Tollen’s reagent?
C. CH3CH2CH2OH
D. CH3OH A. CH3COOH and HCOOCH3
B. HCOOH and HCHO
5. When reacted with a reducing agent, C. CH3COCH3 and CH3CH2CH2OH
aldehyde turn to D. CH3CHO and CH3CH3NH2
A. ketones 8. Which of the following compounds would react
B. carboxylic acids with alkaline iodine solution and with 2,4-
C. secondary alcohols dinitrophenylhydrazine?
D. primary alcohols
A. C6H5CHO
7. An organic compound T, forms a yellow B. C6H5COCH3
precipitate with alkaline iodine solution, but C. CH3CH(OH)CH3
does not react with [Ag(NH3)2]+ solution. D. CH3CH2COCH2CH3
Compound T may be,
A. CH3CHO
B. CH3CH2CH2COCH3
C. CH3CH2COCH2CH3
D. CH3CH2CHO
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EXTRA EXERCISE MODULE CHAPTER 6 2020/2021
9. The intermediate which is formed during 10. Which of the following would attack the
the reaction between propanone and carbon atom in the carbonyl group?
hydrogen cyanide is known as
A. Nucleophile
A. A free radical B. Electrophile
B. A carbonium ion C. Free radical
C. A nucleophile D. Carbonium ion
D. A carbanion
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EXTRA EXERCISE MODULE CHAPTER 6 2020/2021
WORKSHEET 6.7 [Grab your
reader’s
attention
with a great
quote from
the
document
or use this
space to
emphasize
a key point.
To place
this text
box
anywhere
on the
page, just
drag it.]
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EXTRA EXERCISE MODULE CHAPTER 6 2020/2021
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EXTRA EXERCISE MODULE CHAPTER 6 2020/2021
WORKSHEET 6.8
PSPM 2012/2013 DK045
1. Two different compounds P and Q with molecular formula C5H10O have the same skeletal structure.
Compounds P and Q react with 2,4-DNPH to give orange precipitates but there are no observable
changes when reacted with I2/NaOH.
a) Draw the possible structures of P and Q.
Answer : P = Q=
b) Give the IUPAC names of P and Q.
P=
Q=
c) Suggest a chemical test to distinguish between P and Q and write the chemical equations.
Name of test
Equation
Observation
[ 7 marks ]
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EXTRA EXERCISE MODULE CHAPTER 6 2020/2021
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EXTRA EXERCISE MODULE CHAPTER 7 2020/2021
CHAPTER 7: CARBOXYLIC ACIDS
7.1 STRUCTURE AND 7.2 NAMING OF CARBOXYLIC ACIDS
1. Give the general formula of carboxylic acids
Ans:
2. Give the IUPAC name for each compound
(a)
(b)
(c)
(d)
Ans:
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EXTRA EXERCISE MODULE CHAPTER 7 2020/2021
3. Give the IUPAC name for each compound.
Ans:
4. Give the structure corresponding to each name.
(a) 2–bromobutanoic acid
(b) 2,3–dimethylpentanoic acid
(c) 3,3,4–trimethylheptanoic acid
(d) 2–sec–butyl–4,4–diethylnonanoic acid
(e) 3,4–diethylcyclohexanecarboxylic acid
(f) 1–isopropylcyclobutanecarboxylic acid
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EXTRA EXERCISE MODULE CHAPTER 7 2020/2021
(g) 3,3–dimethylpentanoic acid
(h) 4–chloro–3–phenylheptanoic acid
(i) o–chlorobenzoic acid
(j) 4–aminopentanoic acid
Ans:
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EXTRA EXERCISE MODULE CHAPTER 7 2020/2021
7.3 PHYSICAL PROPERTIES
1. Draw the cyclic dimer structure formed between two molecules of propanoic acid.
Ans:
2. What is the main reason carboxylic acid has the highest boiling point as compared to other
compounds with comparable mass?
Ans:
3. Arrange the compounds in each set in order of increasing boiling point:
methanoic acid, propanic acid, butanoic acid, ethanoic acid
Ans:
4. Which following compound is more soluble in water?
(a) Propanoic acid and heptanoic acid.
(b) Ethanoic acid and ethanedioic acid
(c) Ethanol, ethanoic acid and chloroethane.
Ans:
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EXTRA EXERCISE MODULE CHAPTER 7 2020/2021
7.4 PREPARATION
1. Identify A to D (alcohol) in the following reactions.
Ans:
2. Draw the organic products formed in each reaction.
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EXTRA EXERCISE MODULE CHAPTER 7 2020/2021
3. What alcohol can be oxidized to each carboxylic acid?
Ans:
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EXTRA EXERCISE MODULE CHAPTER 7 2020/2021
4. Predict the products of the reactions of the following compounds with acidic solution of Na2Cr2O7.
Write the equation.
(a) 1–hexanol
(b) Ethanol
(c) Acetaldehyde
(d) Hexanal
(e) 1–pentanol
Ans:
7.5 CHEMICAL PROPERTIES
1. Draw the products of each acid–base reaction.
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EXTRA EXERCISE MODULE CHAPTER 7 2020/2021
2. Complete these esterification reactions:
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EXTRA EXERCISE MODULE CHAPTER 7 2020/2021
WORKSHEET 2 (STRUCTURAL QUESTION)
1. Draw the structural formula for each of the following compound.
a. 2-hydroxy-2-phenylethanoic acid
b. 2-chlorobutanedioic acid
c. cis-6-octenoic acid
Ans:
(a)
(b)
(c)
2. TABLE shows the boiling points and solubility of 1-butanol and propanoic acid.
Compound Molecular Boiling point, oC Solubility in water,
mass g/100g
1-butanol 74 117 8.3
Propanoic acid 74 141 ∞
i. Explain why propanoic acid has the highest boiling point and most soluble in water.
Draw the intermolecular forces exist between molecule.
Ans:
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EXTRA EXERCISE MODULE CHAPTER 7 2020/2021
3. The structural formulae of several carboxylic acids A to D are shown below.
COOH
CH3CHCH3 HCOH C COOH
COOH O COOH
A B
D
Which of the above
(a) Dissolves easily in cold water?
(b) Is a solid and dissolves in aqueous NaOH?
(c) Has the highest melting point?
Ans:
4. Draw the structure of P.
Ans:
5. Draw the structure the products for K and L in the following reaction scheme. Give IUPAC name for
the carboxylic acid in the reaction scheme.
CH2COOH
Ans:
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EXTRA EXERCISE MODULE CHAPTER 7 2020/2021
LK
6. The common name of pentanoic acid is valeric acid which can be obtained from Valerian plant. It
has three isomer; 2,2-dimethylpropanoic acid, X and Y. Draw and give the IUPAC name for
compound X and Y.
Ans:
7. Give the product of the reaction between butanoic acid acid and each of the following reagents:
(a) sodium metal
(b) sodium hydroxide
(c) 2-propanol, H2SO4
Ans:
8. Identify compounds A and B in the following reactions.
(a)
O KMnO4, H+ A
CH3 CHCH2 C heat
Cl H
(b)
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EXTRA EXERCISE MODULE CHAPTER 7 2020/2021
9. Show the conversation by using appropriate chemical equation.
OO
CH3CHCOCH3 from CH3CHCOH
CH2CH3 CH2CH3
Ans:
10. Draw the structure of compound A, B and C.
C
PCC CH3
B Mg CH3CHOH A
3-phenylpropanoic acid
H+
Ans:
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EXTRA EXERCISE MODULE CHAPTER 7 2020/2021
WORKSHEET 3 (MIND MAP)
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EXTRA EXERCISE MODULE CHAPTER 7 2020/2021
KMnO4, H+ K
NaOH
CH3CHCH2COOH
CH3
OH H+
Ans:
WORKSHEET (MULTIPLE CHOICE QUESTIONS)
1. Which one of these following compounds is a carboxylic acid?
A. B.
C COOC2H5
O
C. C2H5COO D.
C OH
O
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EXTRA EXERCISE MODULE CHAPTER 7 2020/2021
2. The products of the reaction of a carboxylic acid and an alcohol would be...
A. Ketone and water
B. Amide and water
C. Acid chloride and water
D. Ester and water
3. What is the name of the following compound?
CH3CHCH2COOH
OH
A. 1-carboxylbutanol
B. 1-carboxylbutan-2-ol
C. 3-hydroxybutanoic acid
D. 1,3-dihydroxybutanal
4. Which of the following compounds is known as 2-chlorobenzoic acid?
Cl
A. COOH C.
Cl COOH
B. CHCICOOH D. COOH
Cl
5. Which of the following alcohol can be oxidized to 2-methylpropanoic acid?
A. 2- methyl-1-propanol
B. 2-methyl-2-propanol
C. 2-butanol
D. 2-methyl-2-butanol.
6. A reaction in which a carboxylic acid reacts with a base to form a salt and water is called _____ .
A. neutralization
B. esterification
C.hydrolysis
D.saponification
7. The ester with the smell of bananas has the formula shown below
C3H7CO2C2H5
Which of the following pairs of reagent can be used to prepare this ester?
A. Propanoic acid and ethanol
B. Propanoic acid and 1-propanol
C. Ethanol and butanoic acid
D. 1-propanol and ethanoic acid
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EXTRA EXERCISE MODULE CHAPTER 7 2020/2021
8. Which compound has the highest boiling point?
A. Butane
B. Propanone
C. Acetic acid
D. 1-propanol
9. What factor can decrease the solubility of carboxylic acid in water?
A. The increase in length of the hydrocarbon chain.
B. The decrease in length of the hydrocarbon chain.
C. The increase in number of carboxyl group.
D. The number of hydrogen bond.
10. Choose the correct statement.
A. Ethanoic acid is completely soluble in water because it can dimerise in the presence of water.
B. Ethanoic acid is completely soluble in water because it has 2 carbon atoms.
C. Ethanoic acid is completely soluble in water because it can form hydrogen bond and van der
Waals forces with water molecules.
D. Ethanoic acid is completely soluble in water because it has small hydrophobic group.
MODEL OF PSPM QUESTION
1. Explain the following statements.
4-chlorobutanoic acid is less acidic compared to 2-chlorobutanoic acid
2. TABLE 1 shows the boiling points and solubilities of pentane, 1-butanol, methyl ethanoate
and propanoic acid.
TABLE 1
Compound Molecular mass Boiling point, oC Solubility in water, g/100g
Pentane 72 36 0.04
1-butanol 74 117 8.3
Methyl ethanoate 74 57 24.4
Propanoic acid 74 141 ∞
i. Explain why propanoic acid has the highest boiling point and most soluble?
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EXTRA EXERCISE MODULE CHAPTER 7 2020/2021
ii. Explain why the boiling point of 1-butanol is higher than that of methyl ethanoate whereas
the solubility is the reverse?
[5 marks]
3. Arrange the following compounds in ascending order of acidity. Explain your answer.
2,3-dichlorobutanoic acid, 1-butanol, butanoic acid, 4-clorobutanoic acid,
2-chlorobutanoic acid
[5 marks]
90