Time: 70 Min

M.M: 30

Name: ………………………… Subject: Chemistry

………………………………………………………………………………………………………………………………………………………………………
General Instruction: -

➢ All Questions are compulsory

SECTION -A (4×1=4M)

Q1. The position of –Br in the compound in CH3CH=CHC(Br)(CH3)2 can be Classified as ____________.
(i) Allyl
(ii) Aryl
(iii) Vinyl
(iv) Secondary

Q2. Which reagent will you use for the following reaction.
CH3CH2CH2CH3 → CH3CH2CH2CH2Cl + CH3CH2CHClCH3
(i) Cl2/UV light
(ii) NaCl + H2SO4
(iii) Cl2 gas in dark
(iv) Cl2 gas in the presence of iron in dark

Q3. Which of the following species can act as the strongest base.

Note : 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.
(i) Assertion and reason both are correct and reason is correct explanation of assertion.
(ii) Assertion and reason both are wrong statements.
(iii) Assertion is correct statement but reason is wrong statement.
(iv) Assertion is wrong statement but reason is correct statement.
(v) Both assertion and reason are correct statements but reason is not correct explanation of assertion.
Q4. Assertion : Phenol forms 2, 4, 6 – tribromophenol on treatment with Br2 in carbon disulphide at 273K.
Reason : Bromine polarises in carbon disulphide.
Section -B (3×2=6M)
Q5. Predict the order of reactivity of the following compounds in SN2 reactions:
(i) The four isomeric bromobutanes
(ii) C6H5CH2Br, C6H5CH(C6H5)Br, C6H5CH(CH3)Br, C6H5C(CH3)(C6H5)Br
Q6. Explain why
(i) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.
(ii) Alkyl halides, though polar, are immiscible with water.

Q7. a. While separating a mixture of ortho and para nitrophenols by steam distillation, name the
isomer which will be steam volatile. Give reason.
b. Explain why is ortho nitrophenol more acidic than ortho methoxypheno.
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 Section -C(2×3=6M)
Q8. a. Ethyl chloride is treated with aqueous KOH,
b. Methyl bromide is treated with sodium in the presence of dry ether,
c. Methyl chloride is treated with KCN?
Q9. Write the mechanism of acid catalysed hydration of ethene to yield ethanol.
Section -C (4×1=4M)
Alkene hydration is a catalytic process that involves the addition of water across the double bond of an
alkene to produce an alcohol. This is most direct and atom-economical approach to the synthesis of
alcohols. Acid-catalysed alkene hydration is the most well-known hydration process. This process is used
industrially with several different acidic species as the catalyst, including zeolites, oxides, phosphoric acid
and sulpuric acid. There are several major drawbacks with this catalytic process. The first drawback is the
acidic environment which is very corrosive and can lead to degradation of reactors or the need to use
specially engineered and expensive reactors to resist the acidic conditions. Another drawback is the acidic
environment required for hydration Which is not suitable for alkenes with acid- sensitive functional
groups. Thus, this process Is typically only used with simple alkenes such as ethylene, propylene and
butene. The Final and biggest drawback is the selectivity of the reaction. Acid catalysed hydration Follows
Markovnikov’s rule which states that the proton will add to the carbon with the Most hydrogens attached
to it. Therefore, starting with propylene, acid-catalysed hydration will always be selective for internal
alcohols (secondary or tertiary). Except for ethanol, primary alcohol cannot be synthesized by acid-
catalysed hydration. Generally,
Primary alcohols are the more valuable commodity industrially. Therefore, different synthetic strategies
have to be invented for the synthesis of primary alcohols.
Read the given passage carefully and give the answer of the following questions:

Q1. When propene reacts with water under acidic condition, what is the product formed.
Q2. Write down the Lucas reagent formula.
Q3. Methyl propene when undergoes hydration in presence of acid catalyst, what is the Product
obtained. Also give its structure.
OR
But-1-ene (P) on acidic condition hydration will produce ‘X’ compound, which on Dehydration produce ‘Y’,
acidic condition hydration of ‘Y’ will produce ‘Z’. What happens When X reacts with Na.
Section -E(5×2=10M)
Q10. a. Primary alkyl halide C4H9Br (a) reacted with alcoholic KOH to give compound (b).Compound (b) is
reacted with HBr to give (c) which is an isomer of (a). When (a) Is reacted with sodium metal it gives
compound (d), C8H18 which is different From the compound formed when n-butyl bromide is reacted with
sodium.Give the structural formula of (a) and write the equations for all the reactions.
b. Give the uses of freon-12, DDT, carbon tetrachloride and iodoform.
OR
Write the following Name reactions:
1.Finkelstin Reaction. 2.Benzylic halogenation 3.Sandmayer reaction
4.Balz-Schiman reaction 5.Dow process reaction
Q11. a. Give equations of the following reactions:
(i) Oxidation of propan-1-ol with alkaline KMnO4 solution.
(ii) Bromine in CS2 with phenol.
(iii) Dilute HNO3 with phenol.
(iv) Treating phenol with chloroform in presence of aqueous NaOH.
b. Give reason for the higher boiling point of ethanol in comparison to methoxymethane.
OR
a. How are the following conversions carried out.
(i) Propene to Propan-2-ol.
(ii) Benzyl chloride to Benzyl alcohol.
(iii) Ethyl magnesium chloride to Propan-1-ol.
(iv) Methyl magnesium bromide to 2-Methylpropan-2-ol.
b. Arrange the following compounds in increasing order of their acid strength:
Propan-1-ol, 2,4,6-trinitrophenol, 3-nitrophenol, 3,5-dinitrophenol,Phenol, 4-methylphenol

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