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Ask iit jee aieee pet cbse icse state board community Community Discussion Question: Basicity order
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[Post New]27 Mar 2008 19:22:27 IST
    Subject: Basicity order
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Sushmi (84)

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Check the pic attached below and hence find out the basicity order of the following compounds

Explain your answer too.

    
[Post New]27 Mar 2008 19:24:00 IST
    Subject: Re:Basicity order
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computer001 (1847)

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i think1 and 4 r very weakly basic...but ofcourse im a big 0 @ organic so i cant b trusted
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[Post New]27 Mar 2008 19:29:45 IST
    Subject: Re:Basicity order
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anandghegde (1707)

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A>C>B>D
"I a universe of atoms.......an atom in the universe"
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[Post New]27 Mar 2008 19:31:06 IST
    Subject: Re:Basicity order
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computer001 (1847)

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[Post New]27 Mar 2008 19:33:25 IST
    Subject: Re:Basicity order
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Sushmi (84)

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Explain your answers.
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[Post New]27 Mar 2008 19:38:12 IST
    Subject: Re:Basicity order
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anandghegde (1707)

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The lone pair of electrons in D is involved in aromatisation. Hence the lp is not available for protonation. It is the least basic.

in the remaining three compounds, the lone pair in B is in sp2 orbital and hence tightly bound to the nucleus. Hence it is less basic.

Now compare the remaining two.....In C the lone pair is pulled by the -I effect of oxygen. Hence it is less basic than A.

Hence the order is A>C>B>D
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[Post New]27 Mar 2008 19:38:53 IST
    Subject: Re:Basicity order
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anandghegde (1707)

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@ Gokul. how is A aromatic????
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[Post New]27 Mar 2008 19:40:37 IST
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ninadroxxx (21)

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how is D aromatic
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[Post New]27 Mar 2008 19:41:20 IST
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ninadroxxx (21)

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D is anti aromatoc 4pi electrons and cyclic
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[Post New]27 Mar 2008 19:43:06 IST
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ninadroxxx (21)

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Anand how will u compareb/w B and C In B the lone pair is involved in resonance and in C there is inductive effect so i feel the former dominates
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[Post New]27 Mar 2008 19:44:44 IST
    Subject: Re:Basicity order
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anandghegde (1707)

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in D lone pair of nitrogen is involved in aromatisation man....
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[Post New]27 Mar 2008 19:56:29 IST
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ninadroxxx (21)

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but it is not aromatic
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[Post New]27 Mar 2008 20:38:42 IST
    Subject: Re:Basicity order
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Conjurer (610)

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B is most basic, as conjugate acid is most stable.

EDITED previous post.
Let us learn to dream, gentlemen, and then perhaps we shall learn the truth.
- August Kekule
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[Post New]27 Mar 2008 20:43:48 IST
    Subject: Re:Basicity order
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annihilator (298)

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i think it shld be A>B>C>D
A: its similar to a sec amine
B:the l.p are not involved in conjugation or in aromaticity and hence it's readily available.
C:the electron withdrawing effect of oxygen dec. e` density in N.
D:the electrons are involved in conjugation hence are not available for donation.
Ajay Antony
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[Post New]27 Mar 2008 20:45:02 IST
    Subject: Re:Basicity order
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eistien (343)

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i think the answer is B>A>C>D
 
B is a highly stable compund due to resonance and the lone pair is not involved in it too and so can be easily attacked and thus is most preffered
 
then comes A and then C as there is electron withdrawing nature of electronegative O
 
D is least basic coz the lone pair of N is involved in resonance with the ring and thus makes it aromatic but least basic!!!
 
B>A>C>D!!!
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