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Haloalkanes and Haloarenes Test 7
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Haloalkanes and Haloarenes Test 7
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  • Question 1/17
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    The atom which defines the structure of a family of organic compounds and their properties is called ___________

    Solutions

    Explanation: The atom which defines the structure of a family of organic compounds and their properties is called a functional group. Functional groups are specific groups of atoms or bonds within molecules that are responsible for the characteristic chemical reactions of those molecules.

  • Question 2/17
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    In SN1 reaction, racemisation occurs if the reaction occurs at a stereogenic centre, however, 50:50 mixture of enantiomers are rarely obtained, why?

    Solutions

    In SN1 reaction, some of the substrate, even after ionisation, remains associated as an intimate ion pair preventing nucleophilic attacks from front side and gives inverted product.


    Due to partial reaction of nucleophile with intimate ion pair, net inversion of configuration is observed although predominant reaction occurs at planar carbocation giving racemic products.

  • Question 3/17
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    Pick out the most reactive alkyl halide for an SN1 reaction.

    Solutions

    Tertiary halide would be most reactive in SN1 reaction.

  • Question 4/17
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    Pick out the compound which reacts fastest in the presence of AgNO3.

    Solutions

    Tertiary halide would react at fastest rate with AgNO3 as reaction will proceed by SN1 mechanism.

  • Question 5/17
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    From the following, pick out the explanation for why molecule Y hydrolyses faster than molecule Z.

    Solutions

    Y forms a tertiary carbocation which rearranges to a further more stable benzylic carbocation.

  • Question 6/17
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    Which of the following statement(s) is/are true for SN1 reaction?

    I. The rate of SN1 reaction depends on concentration of alkyl halide
    II. The rate of SN1 reaction depends on concentration of nucleophile
    III. SN1 reactions of alkyl halides are favoured by non-polar solvents

    Solutions

    Rate of SN1 reaction is directly proportional to concentration of alkyl halide but independent of concentration of nucleophile. Non-polar solvents play no role in SN1 reaction.

  • Question 7/17
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    From the following, pick out the potential energy profile for a SN1 reaction.

    Solutions

    SN1 reaction proceeds via carbocation intermediate which is being indicated here by two transition states and a small trough between reactant and product. Also the second transition state must be below first transition state in SN1 reaction

  • Question 8/17
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    The most and least reactive electrophiles respectively in a SN1 reaction are


    Solutions

    Electron donating —CH3 gro up stabilises benzylic carbocation, hence increases reactivity of corresponding substrate. Electron withdrawing —NO2 decreases stability of carbocation, decreases reactivity of corresponding substrate in SN1 reaction

  • Question 9/17
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    Pick out the strongest substrate(s) for a SN1 reaction.

    Solutions

    It forms a secondary carbocation which, by hydride shift, rearranges to a tertiary carbocation.

  • Question 10/17
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    Pick out the following factor(s) which promote a SN1 reaction :

    I. Temperature
    II. Concentration of nucleophile
    III. Concentration of alkyl halide
    IV. Aprotic solvents

    Solutions

    Increasing temperature increases rate of any reaction. Also, rate of SN1 reaction is directly proportional to concentration of alkyl halide but independent of nucleophile and aprotic solvent.

  • Question 11/17
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    Which of the following alkyl halides is respectively most and least electrophilic in SN1 reaction?

    Solutions

    (III) forms tertiary carbocation, hence most reactive. (I) is least reactive as highly unstable carbocation is formed at bridge head carbon of bicyclic compound.

  • Question 12/17
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    Which of the following is true regarding a SN1 reaction?

    Solutions

    Protic solvents solvate carbocation, promotes SN1 reaction.

  • Question 13/17
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    Rank the following molecules increasing in order of relative rate of SN1 solvolysis with methanol and heat.

    Solutions

    (V) form s m ost stable, tertiary allylic, carbocation. (II) is vinylic halide, least reactive.

  • Question 14/17
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    Which is the most likely product when the following iodide is heated with water?

    Solutions


  • Question 15/17
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    What is the correct order of reactivity of the followings in hydrolysis reaction at elevated temperature?

    Solutions

    (II) is most reactive as it forms aromatic carbocation (III) is next most reactive as it forms allylic carbocation. (I) is least reactive as it forms least stable cyclopropyl carbocation.

  • Question 16/17
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    Statement Type

    Direction (Q. Nos. 16 and 17) This section is based on Statement I and Statement II. Select the correct answer from the codes given below.

    Q.

    Consider the following two bromides I and II, undergoing solvolysis reaction in boiling ethanol :


    Statement I : I is less reactive than II in the given solvolysis reaction.

    Statement II : Resonance stabilisation available with the intermediate formed from II is the important driving force.

    Solutions

    (II) forms more stable carbocation than (I).

  • Question 17/17
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    Statement I : When 3-bromo propene, which contain a labelled 13C at C-1 position is refluxed with methanol, following products were obtained.

    Statement II : Methanol has an acidic proton bonded to oxygen.

    Solutions

    Both statements are true but the two different products are due to resonance in carbocation intermediate as

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