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Ask iit jee aieee pet cbse icse state board community Community Discussion Question: ACIDITY
Forum Index -> Organic Chemistry like the article? email it to a friend.  
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x4 (300)

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WHICH ONE HAS HIGHER ACIDITY ?  STRONGER BASE ??


 


    C – NH2


  /    \


C    C                                   COMPOUND 1


 |      |


C    C


  \    /


    C


 


 


CH3---CH2---NH2                   COMPOUND 2


 


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ashish_banga (937)

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second
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sandeepramesh (1245)

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why the sudden flurry of questions? :huh:huh:huh :D :D


i think it will be 2 bcos in 1, the C is having sp2 char no?

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x4 (300)

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SP2 CHAR IN 1 MUST INCREASE ELECTRON DENSITY THAT IN 2 COZ ITS SP3 RIGHT ?

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sandeepramesh (1245)

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sp2 char might make it a bit en withdrawing thus decr the en density no? :huh:huh

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x4 (300)

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ANSWER THE OTHER ONE NO . THINK IN TERMS OF HYDROGEN BONDING . THATS IF IM RIGHT .

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sandeepramesh (1245)

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i answered :huh and see ur nudges often :huh

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ashish040191 (135)

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ther is no C with sp2 hbridisation in any of the given molecules.


on the basis of +I  carbon atoms basic strrength can b judged.


since no. of C atoms in 1st ismore. her4 electron density at N is more.ther4 more is the ease of donation of lone pair(so more basic strength)

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Mr.IITIAN007 (2985)

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1st one is more acidic and the second one is more basic .........cuz of presence of methyl gp in the second compound which is quite a strong +I gp and makes the compund more basic, soluble and less tendency to act as a leaving gp .


Ken
From: UNITED STATES, Green Bay, Wisconsin
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sandeepramesh (1245)

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mr. ashish040191 havent you learnt that in a cyclic ring, all the carbons are like sp2 hybridised? :huh:huh

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shreyasnivas (256)

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sandeepramesh i think you are talking about benzene ring.. for cyclo hexane all carbons are and behave like sp3.


i think this problem is a mixture of


1) number of carbon atoms


2) steric hindrance to protonation.


these 2 are competing factors. in questions like these its sometimes really hard to say which is more acidic..


the only wayto know for sure is when there is clear data. otherwise in jee and all they only ask such questions where the answer is obvious by using techniques that students can think of.


each persons answer is as good as the other's.


im not trying to sound like some great preacher.. just telling you something my organic chem teacher had once told me.. and she is quite knowledgeable.

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sandeepramesh (1245)

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no im talking abt cyclic rings only

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ashish040191 (135)

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mr.  sandeepramesh, 


who the damn told u that all C of cyclic rings are sp2 hyb.????????????????.mind it,,,,,,,, 


carbns of cyclohexane are sp3 hyb.!!!!!!!!!!!!!!!!!!! and this is what i wrote. carbons are sp2 hyb. when it has 1 pie bond.


right?????

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shubham.123 (302)

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ya dude
u r right!
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sandeepramesh (1245)

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