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    Aromaticity: Aromaticity: Benzenoid and Non-Benzenoid Compounds - Generation and Reactions

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    Sankar Adhikari
    The document discusses aromaticity and provides examples of questions and solutions related to aromatic compounds from past exams. It examines the properties of different aromatic rings and heterocycles, including their acidity, basicity, dipole moments, NMR spectra, and whether they follow Hückel's rule to be aromatic, antiaromatic, or nonaromatic. Key topics covered include the ordering of acidity/basicity, identification of aromatic versus antiaromatic structures, and effects of substituents on aromaticity and magnetic properties.

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    Aromaticity: Aromaticity: Benzenoid and Non-Benzenoid Compounds - Generation and Reactions

    Uploaded by

    Sankar Adhikari
    626 views7 pages
    The document discusses aromaticity and provides examples of questions and solutions related to aromatic compounds from past exams. It examines the properties of different aromatic rings and heterocycles, including their acidity, basicity, dipole moments, NMR spectra, and whether they follow Hückel's rule to be aromatic, antiaromatic, or nonaromatic. Key topics covered include the ordering of acidity/basicity, identification of aromatic versus antiaromatic structures, and effects of substituents on aromaticity and magnetic properties.

    Original Description:

    Questions and answers on Aromaticity

    Original Title

    Aromaticit y

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    The document discusses aromaticity and provides examples of questions and solutions related to aromatic compounds from past exams. It examines the properties of different aromatic rings and heterocycles, including their acidity, basicity, dipole moments, NMR spectra, and whether they follow Hückel's rule to be aromatic, antiaromatic, or nonaromatic. Key topics covered include the ordering of acidity/basicity, identification of aromatic versus antiaromatic structures, and effects of substituents on aromaticity and magnetic properties.

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    © All Rights Reserved
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    Download as docx, pdf, or txt
    626 views7 pages

    Aromaticity: Aromaticity: Benzenoid and Non-Benzenoid Compounds - Generation and Reactions

    Uploaded by

    Sankar Adhikari
    The document discusses aromaticity and provides examples of questions and solutions related to aromatic compounds from past exams. It examines the properties of different aromatic rings and heterocycles, including their acidity, basicity, dipole moments, NMR spectra, and whether they follow Hückel's rule to be aromatic, antiaromatic, or nonaromatic. Key topics covered include the ordering of acidity/basicity, identification of aromatic versus antiaromatic structures, and effects of substituents on aromaticity and magnetic properties.

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    © All Rights Reserved
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    of 7

    Aromaticity

    Aromaticity: Benzenoid and non-benzenoid compounds – generation and reactions.

    JUN- DEC- JUN- DEC- JUN- DEC- JUN- DEC- JUN- DEC- JUN-
    YEAR 2016 2015 2015 2014 2014 2013 2013 2012 2012 2011 2011
    No.of
    questions
    appeared 1 – 1 2 1 1 1 2 – 1 2

    1.The correct order of pKa values for the compounds X, Y and Z is……

    Ans (3)

    Soln:

    More acidic strength of compound less will be pka value.

    ‘Y’ is most acidic due to presence of strong electron withdrawing and to gain aromatic character So, it
    has least pka value ‘Z’ is least acidic, due to more Annelation effect of two Benzene ring so, It have
    highest pka value therefore order of pka value Z > X > Y

    2.The compound that is antiaromatic is

    (a) I

    (b) II

    (c) III

    (d) IV

    Ans (a)

    Soln:
    1
    Only I one follows huckel rule and contain 4nπ electron system

    II and IV are aromatic

    III is non aromatic due to sp3 carbon.

    3.The decreasing order of basicity of the following compounds is

    (a) I > II > III > IV

    (b) IV > I > II > III

    (c) III > II > I > IV

    (d) IV > III > II > I

    Ans (c)

    Soln:

    Basicity depends on the ease of donating lone pair or greater the electron density greater will be the
    basic character

    Pyridine is least basic as it is part of sp2 ring system.

    Highest electron density will be of guanidine group. Hence C is the correct option

    Refrerence : Organic Chemistry, Clayden.

    4.The correct order of basicity for the following anions is

    (a) II > III > I

    (b) I > II > III

    2
    (c) II > I > III

    (d) III > II > I

    Ans (c)

    Soln:

    In case of ortho and para resonance as well as inductive effect both operate.

    Thus, electron withdrawl will be more in the case of ortho and para substituted nitro phenol.

    Thus, conjugate base of ortho and para will be less basic.

    Meta substituted phenoxide (II) will be most basic.

    Now, in between I and III, since H-bonding (intramolecular) occurs in the case of I, it is less

    acidic as com-pared to para, thus it will be more basic as compared to III.

    => II > I > III.

    5.Amongst the following, the compound which has the lowest energy barrier for the cis-trans
    isomerisation is:

    Ans (c)

    Soln

    3
    Among all options, option (c) has gain aromaticity in both the rings. Therefore, the lowest energy barries
    for cis-trans isomerisation is option (c)

    6.Among the following compounds, the one which has highest dipole moment is

    Ans (b)

    Soln:

    The compound which have maximum charge separation, have highest dipole moment.

    This compound is aromatic in nature, and have maximum charge separation. So, it have highest dipole
    moment.

    7.The correct order of acidity of the compounds A – C is:

    (a) A > B > C

    (b) B > C > A

    (c) C > A > B

    4
    (d) B > A > C

    Ans (c)

    Soln:

    Acidity ∝E.W. tendency.

    So, the correct order of acidity is C > A > B.

    8.Consider the following statements for [18]-annulene

    (A) It is aromatic

    (B) The inner protons resonate at δ9.28 in its 1H NMR spectrum

    (C) There are six protons in the shielded zone.

    (a) A, B, C

    (b) A and B only

    (c) B and C only

    (d) A and C only

    Ans (d)

    Soln:

    5
    [18] annulene is aromatic compound and shows ring current

     The ring current produces strong induced magnetic field.


     Outer 12 protons appears at 8.9 ppm because they remains in deshielding zone.

    Inner six protons appears at – 1.8 ppm because they remains in shielding zone (up-field)

    Hence, statement A and C are correct.

    9.Among the carbocations given below

    (a) A is homoaromatic, B is antiaromatic and C is aromatic.

    (b) A is aromatic, B is antiaromatic and C is homoaromatic.

    (c) A is antiaromatic, B is aromatic and C is harmoaromatic.

    (d) A is homoaromatic, B is aromatic and C is antiaromatic.

    Ans (a)

    10.The correct order of acidity of the following compound A–C is:

    6
    (a) B > C > A

    (b) C > B > A

    (c) A > C > B

    (d) A > B > C

    Ans (c)

    11.Among A-C, the aromatic compounds are

    (a) A, B and C

    (b) A and B only

    (c) B and C only

    (d) A and C only

    Ans (c)

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