-I am having trouble understanding 1) how to rank compound starting byacidity. e

Question

-I am having trouble understanding     1) how to rank compound starting byacidity.              ex: Rankthe follwing starting with the most to least acidic                     a) ClCH2CH2OH      b)CH3CH2OH       c) CH3CH2NH2    2) how to recognize the most acidic hydrogenin compounds          ex:                   a)CH3CH2CH2OH     b) HOCH2CH2CH2NH2    3) how do I tell if a compound is mostlypolar, nonpolar, or ionic and when a compounds dipole moment iszero.       ex: CH3Cl    4) how to rank for water solubilitygiven         ex: a)(CH3)3 CH b)CH3OCH2CH3   c)CH(CH2)2CH3      d)CH3(CH2)2OH        5) and I"m guessing torank increasing-decreasing order of boiling points ofcompounds just by looking at for instance,CH3(CH2)4CH3   and (CH3)2CHCH(CH3)2 hassomething to do with int. forces but I am lost, can you give mesome clues on this stuff?! THANK YOU! -I am having trouble understanding     1) how to rank compound starting byacidity.              ex: Rankthe follwing starting with the most to least acidic                     a) ClCH2CH2OH      b)CH3CH2OH       c) CH3CH2NH2    2) how to recognize the most acidic hydrogenin compounds          ex:                   a)CH3CH2CH2OH     b) HOCH2CH2CH2NH2    3) how do I tell if a compound is mostlypolar, nonpolar, or ionic and when a compounds dipole moment iszero.       ex: CH3Cl    4) how to rank for water solubilitygiven         ex: a)(CH3)3 CH b)CH3OCH2CH3   c)CH(CH2)2CH3      d)CH3(CH2)2OH        5) and I"m guessing torank increasing-decreasing order of boiling points ofcompounds just by looking at for instance,CH3(CH2)4CH3   and (CH3)2CHCH(CH3)2 hassomething to do with int. forces but I am lost, can you give mesome clues on this stuff?! THANK YOU!

Explanation / Answer

   1) For acidity, we need to apply the following rules :       Bronsted's rule : An acid donates a H+ ion, while abase accepts H+ ion    Lewis' rule : An acid accepts a lone pair of electron, while abase donates a lone pair of electrons        Now, we check the tendency to donate H+ ion oraccept lone pair of electrons in this case, which gives the order:       ClCH2CH2OH> CH3CH2OH >CH3CH2NH2       2) The most acidic hydrogen is the one which is attached tothe most electronegative atom, which here is oxygen O.       a) The last H atom, of -OH group is most acidic    b) The first H atom, of -OH group is most acidic.       3) When different atoms are attached to the central atom, orwhen linear pairs are present, which disorient the    arrangement, or molecule is non-symmetric, atom is polar, andhas dipole moment       CH3Cl - Here, since different atoms (H and Cl) areattached to central atom, it is polar and has dipole moment.       4) More is the polarity, more is the solubility of compound(since wate itself is polar)    Here, the order of polarity, and thus of solubility is :       CH3(CH2)2OH >CH3OCH2CH3 >CH(CH2)2CH3 >(CH3)3CH    5) More is the branching, more is the intermolecular force,and more is the boiling point.    Here, it is(CH3)2CHCH(CH3)2    

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