VISHWA BHARATI PUBLIC SCHOOL, NOIDA

CLASS XII
HOLIDAY HOMEWORK - CHEMISTRY
Prepared by: Ms. Pragya Pant
Topics: Haloalkanes and Haloarenes, Alcohols, Phenols and Ethers

A. Multiple Choice Questions

1. Which of the following compounds is expected to be optically active?

(a) (CH3)2CHCHO (b) CH3CH2CH2CHO
(c) CH3CH2CHBrCHO (d) CH3CH2CBr2CHO
2. The halogen compound which most readily undergoes nucleophilic substitution is
(a) CH2 = CHCl (b) CH3CH = CHCl
(c) CH2 = CHC(Cl) = CH2 (d) CH2 = CHCH2Cl
3. What is the major product in the following reaction
CH3 O-
(CH3)2 – CH – CH2Br →
CH3 OH
(a) (CH3)2CHCH2OCH3 (b) CH3CH(OCH3)CH2CH3
(c) (CH3)2 C = CH2 (d) (CH3)3C(OCH3)
4. Phenyl magnesium bromide on reaction with tert-butyl alcohol gives
(a) Benzene (b) Phenol
(c) Tert-butyl benzene (d) Tert-butyl phenyl ether
5. On monochlorination of 2-methylbutane, the total number of chiral compounds formed is:
(a) 2 (b) 4
(c) 6 (d) 8
6. An SN2 reaction at an asymmetric carbon of a compound always gives:
(a) An enantiomer of the substrate (b) A product with opposite optical rotation
(c) A mixture of diastereomers (d) A single stereoisomer
7. Which of the following shows SN1 reaction most readily
(a) (b)

(c) (d)

8. Arrange in increasing order of acid strength: p-methoxyphenol, p-methylphenol and p-nitrophenol

is:
(a) p-nitrophenol, p-methoxyphenol, p-methylphenol
(b) p-methylphenol, p-methoxyphenol, p-nitrophenol
(c) p-nitrophenol, p-methylphenol, p-methoxyphenol
(d) p-methoxyphenol, p-methylphenol, p-nitrophenol
9. Phenol on treatment with CHCl3 and NaOH forms
(a) Benzaldehyde (b) Salicylaldehyde
(c) Salicylic acid (d) Benzoic acid

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10. The product of acid-catalysed hydration of 2-phenylpropene is
(a) 3-phenylpropan-2-ol (b) 1-phenylpropan-2-ol
(c) 2-phenylpropan-2-ol (d) 2-phenylpropan-1-ol
11. Toluene reacts with a halogen in the presence of iron (III) chloride giving ortho and para halo
compounds. The reaction is
(a) Electrophilic elimination reaction (b) Electrophilic substitution reaction
(c) Free radical addition reaction (d) Nucleophilic substitution reaction
12. Chlorobenzene is formed by reaction of chlorine with benzene in the presence of AlCl 3. Which of
the following species attacks the benzene ring in this reaction?
(a) Cl– (b) Cl+
(c) AlCl3 (d) [AlCl4]–
13. What should be the correct IUPAC name for diethylbromomethane?
(a) 1-Bromo-1,1-diethylmethane (b) 3-Bromopentane
(c) 1-Bromo-1-ethylpropane (d) 1-Bromopentane

14. Which is the correct increasing order of boiling points of the following compounds?
1-Bromoethane, 1-Bromopropane, 1-Bromobutane, Bromobenzene
(a) Bromobenzene < 1-Bromobutane < 1-Bromopropane < 1-Bromoethane
(b) Bromobenzene < 1-Bromoethane < 1-Bromopropane < 1-Bromobutane
(c) 1-Bromopropane < 1-Bromobutane < 1-Bromoethane < Bromobenzene
(d) 1-Bromoethane < 1-Bromopropane < 1-Bromobutane < Bromobenzene

15. Identify the compound Y in the following reaction

(a) (b)

(c) (d)

16. Which of the following species can act as the strongest base?
(a) –OH (b) –OR
(c) –OC6H5 (d)

17. CH3CH2OH can be converted into CH3CHO by ______________.

(a) catalytic hydrogenation (b) treatment with LiAlH4
(c) treatment with pyridinium chlorochromate (d) treatment with KMnO4

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18. The increasing order of reactivity of the following compounds with HBr/HCl is:

(i) (ii) (iii)

(a) (i) < (ii) < (iii) (b) (ii) < (i) < (iii)
(c) (ii) < (iii) < (i) (d) (iii) < (ii) < (i)
19. The position of –Br in the compound in CH3CH=CHC(Br)(CH3)2 can be classified as
(a) Allyl (b) Aryl
(c) Vinyl (d) Secondary
20. Arrange the compounds in increasing order of rate of reaction towards nucleophilic substitution

(i) (ii) (iii)

(a) (i) < (ii) < (iii) (b) (ii) < (i) < (iii)
(c) (iii) < (ii) < (i) (d) (i) < (iii) < (ii)
21. During dehydration of alcohols to alkenes by heating with conc. H2SO4, the initial step is
(a) Formation of ester (b) Protonation of alcohol
(c) Formation of carbocation (d) Elimination of water
22. Acetone reacts with Grignard reagent to give
(a) 3◦ alcohol (b) 2◦ alcohol
(c) Ether (d) No reaction
23. Isopropyl benzene on air oxidation in the presence of dilute acid gives
(a) C6H5COOH (b) C6H5COCH3
(c) C6H5CHO (d) C6H5OH
24. When sodium ethoxide and ethyl bromide are heated they yield:
(a) Diethyl ether (b) Ethyl alcohol
(c) Acetaldehyde (d) Acetic acid
25. Which of the following can not be prepared by Williamson synthesis?
(a) Methoxybenzene (b) Benzyl p-nitrophenyl ether
(c) tert-butyl methyl ether (d) di-tert-butyl ether
B. Assertion Reasoning Questions

In the following questions a statement of assertion followed by a statement of reason is given.

Choose the correct answer out of the following choices.
(a) Assertion and reason both are correct and reason is correct explanation of assertion.
(b) Assertion and reason both are wrong statements.

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 (c) Assertion is correct but reason is wrong statement.
(d) Assertion is wrong but reason is correct statement.
(e) Assertion and reason both are correct statements but reason is not correct explanation of
assertion.

1. Assertion(A): p-Nitrophenol is more acidic than phenol.

Reason(R): Nitro group helps in the stabilisation of the phenoxide ion by the
dispersal of negative charge due to resonance.
2. Assertion(A): Bromobenzene upon reaction with Br2/Fe gives 1,4-dibromobenzene as
the major product.
Reason(R): In bromobenzene, the inductive effect of the bromo group is more
dominant than the mesomeric effect in directing the incoming electrophile.
3. Assertion : Nitration of chlorobenzene leads to the formation of m-nitrochlorobenzene
Reason : —NO2 group is a m-directing group
4. Assertion : It is difficult to replace chlorine by –OH in chlorobenzene in comparison to that
in chloroethane.
Reason : Chlorine-carbon (C—Cl) bond in chlorobenzene has a partial double bond
character due to resonance.
5. Assertion : Phosphorus chlorides (tri and penta) are preferred over thionyl chloride for the
preparation of alkyl chlorides from alcohols.
Reason : Phosphorus chlorides give pure alkyl halides.
6. Assertion : Addition reaction of water to but-1-ene in acidic medium yields butan-1-ol
Reason : Addition of water in acidic medium proceeds through the formation of primary
carbocation.
7. Assertion : Bond angle in ethers is slightly less than the tetrahedral angle.
Reason : There is a repulsion between the two bulky (—R) groups.
8. Assertion : o-Nitrophenol is less soluble in water than the m- and p-isomers.
Reason : m- and p- Nitrophenols exist as associated molecules.
9. Assertion : Phenol forms 2, 4, 6 – tribromophenol on treatment with Br2 in carbon
disulphide at 273K.
Reason : Bromine polarises in carbon disulphide.
10. Assertion : The boiling points of alkyl halides decrease in the order :
RI > RBr > RCl > RF
Reason : The boiling points of alkyl chlorides, bromides and iodides are considerably
higher than that of the hydrocarbon of comparable molecular mass.

C. Case study based

1. An alkyl halide with β-hydrogen atoms when reacted with a base or a nucleophile has two
competing routes: Substitution (SN1 and SN2) and elimination(E1 and E2). Which route will be taken
up depends upon the nature of the alkyl halide, strength and size of the base/nucleophile and reaction
conditions. Thus, bulkier nucleophile prefers to act as a base and abstracts a proton rather than
approaching a tetravalent carbon atom (steric reasons) and vice-versa. A primary alkyl halide can
react either by SN2 or E2 mechanism, a secondary halide can react by either of the four mechanisms
(SN1, SN2, E1 and E2) depending on the stability of the intermediate carbocation or the substituted

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 alkene formed and the reaction conditions. A tertiary alkyl halide can react through three possible
pathways (SN1, E1 and E2).
a. Write the product obtained when isopropyl bromide is heated with a concentrated solution
of alcoholic KOH.
b. Differentiate between SN1 and SN2 reaction.
c. Define retention, inversion and racemisation

2. Both alcohols and phenols contain a hydroxyl group, but phenols are more acidic than alcohols.
The reason being that the phenoxide ion left after the removal of a proton is stabilized by resonance
while the alkoxide ion is not. Therefore, phenols dissolve in aqueous sodium hydroxide but alcohols
do not. However, both are weaker acids than carbonic acid and hence do not decompose aqueous
NaHCO3 solution evolving CO2. The presence of electron-donating groups in the benzene ring
decreases the acid strength while the presence of electron-withdrawing groups in the benzene ring
increases the acid strength of phenols. The relative strength of o-, m- and p-substituted phenols,
however, depends on a combination of inductive and resonance effects of the substituent.
a. What is the order of reactivity of primary, secondary and tertiary alcohols towards sodium
metal?
b. Write the reaction of tert-butyl alcohol with Aluminium.
c. Arrange in the increasing order of acidic strength and explain the order: alcohol, phenol,
water

3. Grignard reagents are very versatile organometallic compounds. Due to the large electronegativity
difference between carbon and magnesium, the C-Mg bond has significant ionic character. The
hydrocarbon part of the Grignard reagent acts as a source of carbanions. Therefore, Grignard
reagents undergo nucleophilic addition reactions to aldehydes/ketones forming the addition
products which upon hydrolysis yield alcohols.
a. Write the reaction for the addition of excess CH3MgBr to ethyl formate followed by
hydrolysis.
b. Why should Grignard reagents be stored in a moisture free environment?
c. Illustrate the reaction of aldehydes and ketones with Grignard reagent
D. Subjective Questions

Unit 6: Haloalkanes and haloarenes

1. Compound ‘A’ with molecular formula C4H9Br is treated with aq. KOH solution. The rate of this
reaction depends upon the concentration of the compound ‘A’ only. When another optically active
isomer ‘B’ of this compound was treated with aq. KOH solution, the rate of reaction was found to be
dependent on concentration of compound and KOH both.
(a) Write down the structural formula of both compounds ‘A’ and ‘B’.
(b) Out of these two compounds, which one will be converted to the product with inverted
configuration.

2. Does the presence of two chiral carbon atoms always make the molecule optically active? Explain
with an example.

3. Explain the decreasing order of reactivity of the following towards nucleophilic substitution reaction:
allyl chloride > n-propyl chloride > vinyl chloride

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4. Out of the various possible isomers of C7H7Cl containing a benzene ring, suggest the structure with
the weakest C-Cl bond.

5. What happens when:

a. Ethylbenzene reacts with Br2 in the presence of light
b. sec-butyl chloride is treated with alcoholic KOH
c. Isopropyl magnesium bromide is treated with heavy water

6. Give a chemical test to distinguish between:

a. Chlorobenzene and ethyl chloride
b. Bromoethane and Iodoethane
c. n-propyl bromide and isopropyl bromide

7. Write the major and minor products in the following reaction

𝑎𝑙𝑐.𝐾𝑂𝐻
C6H5CH2CHClC6H5 →
∆

8. Convert:
a. Butene to Iodobutane
b. Propan-2-ol to 1-bromopropane
c. methyl bromide to ethyl bromide
d. propene to 1-bromopropane
e. 2-bromopropane to 1-bromopropane

9. Identify X, Y, Z in each of the following reactions

𝐻𝐵𝑟 𝑎𝑞. 𝐾𝑂𝐻 𝐼2 ,𝑁𝑎𝑂𝐻
a. C2H4 → X→ Y→ Z
𝑎𝑙𝑐. 𝐾𝑂𝐻 𝐵𝑟2 𝑎𝑙𝑐. 𝐾𝑂𝐻
b. C2H5Br → X→ Y→ Z

𝐶𝑙2 /𝐹𝑒 𝐶𝑢𝐶𝑁 𝐻 + , 𝐻2 𝑂

c. C6H6 → X → Y→ Z
𝑝𝑦,∆
𝑁𝑎𝑁𝑂2 ,𝐻𝐶𝑙 𝐶𝑢𝐵𝑟/𝐻𝐵𝑟 (𝐶𝐻3𝐶𝑂)2 𝑂
d. C6H5NH2 → X→ Y→ Z
273−278𝐾 𝑎𝑛ℎ𝑦𝑑.𝐴𝑙𝐶𝑙3
𝐶𝐻3 𝐶𝑙 𝐶𝑙2 /ℎ𝜐 𝐾𝑂𝐻
e. C6H6 → X→ Y→ Z
𝑎𝑛ℎ𝑦𝑑.𝐴𝑙𝐶𝑙3

10. Explain why

a. Neopentyl bromide undergoes nucleophilic substitution reaction very slowly.
b. 3-bromocyclohexene is more reactive than 4-bromocyclohexene in hydrolysis with aq. NaOH.
c. vinyl chloride is unreactive in nucleophilic substitution reactions.
d. halogen in chlorobenzene is less reactive than in methyl chloride.
e. Wurtz reaction fails in case of tert-alkyl halides.
f. Lewis acids are used in the preparation of aryl bromides and chlorides in the dark.
g. Explain why the hydrolysis of chlorocyclohexane is easier than that of chlorobenzene.
h. Aryl halides not be prepared by reaction of phenol with HCl in the presence of ZnCl2

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Unit 7: Alcohols, phenols and ethers

1. Account for the following:

a. di-tert-butyl ether cannot be prepared by Williamson synthesis
b. anisole is less reactive than phenol towards electrophilic substitution reactions.
c. acid catalysed dehydration of tert-butyl alcohol is faster than that of n-butyl alcohol.
d. methyl phenyl ether reacts with HI to give phenol and methyl iodide and not iodobenzene and
methyl alcohol.
e. The order of reactivity of halogen acids towards cleavage of ethers is HI > HBr > HCl
f. Nitration of phenol gives o-, p- products only.
g. alcohols are soluble in water but alkyl halides are not.
h. Alcohols have higher boiling points than corresponding hydrocarbons but lower boiling points
than corresponding phenols.
i. Dipole moment of methanol is higher than that of phenol.
j. The order of reactivity of alcohols follows the order: Primary > Secondary > Tertiary
k. ethers possess a net dipole moment even if they are symmetrical in structure.
l. The C – O – C bond angle in ethers is greater than the H – O – H bond angle in water, even though
oxygen is sp3 hybridised in both cases.
m. Alcohols react with halogen acids or phosphorus halides to form haloalkanes but phenols do not
form halobenzenes.

2. Convert:
a. Chlorobenzene to phenol
b. phenol to 4-bromophenol
c. phenol to 2-acetoxybenzoic acid
d. acetone to tert-butyl alcohol
e. propanone to 2-methylpropan-2-ol
f. methanol to ethanol
g. ethanol to ethoxyethane
h. phenol to acetophenone
i. anisole to phenol
j. ethyl magnesium bromide to propan-1-ol

3. How will you distinguish between the following pairs of compounds:

a. propanol and propan-2-ol
b. phenol and methanol
c. ethanol and propanol
d. phenol and acetic acid
e. sec-butanol and tert-butanol

4. Complete the following equations

𝑐𝑜𝑛𝑐. 𝐻2 𝑆𝑂4
a. C2H5OH →
443 𝐾
𝐶𝑢
b. C2H5OH →
573 𝐾
𝐻2 𝑂
c. C6H5OH + Br2 →

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 𝐻3 𝑃𝑂4
d. C6H6 + CH3 – CH = CH2 →
𝑁𝑎𝑂𝐻
e. C6H5COCl + C6H5OH →

5. What happens when

a. Phenol is treated with neutral FeCl3
b. Phenol is warmed with CCl4 in the presence of aq. NaOH
c. Ethanoyl chloride is treated with phenol
d. Phenol is treated with conc. HNO3 in the presence of conc. H2SO4
e. Phenol is reacted with CO2 at 400K and 4-7 atm pressure
f. Phenol is treated with excess of bromine water.

6. Describe Lucas test to distinguish between primary, secondary and tertiary alcohols. Can we use
this test as a test for Phenol?

7. What happens when primary, secondary and tertiary alcohols are:

a. Oxidised using alkaline KMnO4
b. Passed over heated Cu at 570K

8. Give the mechanism for the preparation of ethoxyethane from ethanol.

9. Illustrate the mechanism of reaction of HI with Methoxyethane.

10. Write the structure of the major product obtained from the dinitration of 3-Methylphenol.

11. Write the equation of the reaction of Hydrogen Iodide with:

a. Benzyl ethyl ether
b. tert-butyl methyl ether

12. Which of the following is the correct method for synthesising methyl-tert-butyl ether and why?
a. (CH3)3CBr + NaOMe
b. CH3Br + NaO-tert-Bu

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