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Ask iit jee aieee pet cbse icse state board community Community Discussion Question: basicity(easy one)
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svj29 (2140)

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the correct order of basicity of following compounds is(plz xplain d ansr, all opitons):
1.     
                  CH3-C-NH2
                          ||
                         N(+)H2
2.CH3CH2NH2
 
3.(CH3)2NH
 
4.CH3CONH2
 
1. 2>1>3>4
2.1>3>2>4
3.3>1>2>4
4.1>2>3>4
 
the ansr is 2>1>3>4 as postd in d ansr sheet....
sry 4 nt posting d options earlier...
    
tarinbansal (3903)

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Wat's the meaning of (+) in first option?

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svj29 (2140)

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(+) charge on N....

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tarinbansal (3903)

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There is some problem in the order given by U.
4 is least basic for sure but how can 3 be less basic than 2?
3 is definitely more basic than 2.

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tarinbansal (3903)

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Arre N pe + kahan se aa gaya? N ki teeno valencies complete hain.
The + charge must be on C.

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svj29 (2140)

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i dunno...N ki 4 valency hai...chck again and tl d ordr according to ya... cz tis a quesn of by booklt...so ans cn also be wrong...

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tarinbansal (3903)

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I am getting 1>3>2>4.

Let others also reply so that we can confirm the ans. If my ans is found to be correct, I will post the explanation.

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svj29 (2140)

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post it rite nw......if ur xplanation is crct dn ur ansr also shud be crct....cmon odrs try it....

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dutta1 (11)

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the ans 2134 is corect acc to me
but i think there should not be any + charge on n
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svj29 (2140)

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ya bro ur crct... giv ur xplanation....
and dere is +chrge on N..widout it N cn't have 4 valency...

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tarinbansal (3903)

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Wait, I think the answer shud be 3>2>4>1.

See 4 is least among 2,3 basic due to electron withdrawing effect of C=O both by resonance as well as by inductive.
Now 3>2>4 due to more electron pushing inductive effect of 2 CH3 groups in 3.

Now in 1, u can see that if u do resonance between double bond of one N and lone pair of other N, U get 2 idenctical resonance structures. it means the given compound is very stable. But U can't put one more H+ on the already +ve N and if U put the H+ on the other N, the compound will become highly unstable due to 2 +ve charges. Hence it cannot accept H+ and hence is least basic
 
EDITED THE LAST REASON. HAD POSTED THE WRONG REASON EARLIER.

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tarinbansal (3903)

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dutta1,
can U please explain how did u get 2134?

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dutta1 (11)

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4 n is with c=o there by resonance no e on N so least basic
3 1 e donating gp
1 + charge attaract double bounded e
2 3 e donating gp attached

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dutta1 (11)

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sorry for late reply
i was also looking something else...
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