organic discussion!

"nucleophilicity runs parallel to basicity when the nucleophilic atom is the same in various species"

97 Answers

1
? ·

arre sorry R-O-

1
? ·

u are just considering the negative charge !!

but there are other things too !

3
msp ·

the order shud be

RCOO-> RCO- > ROH > RCOOH

1
voldy ·

RCO- ??????????

1
? ·

good then how can we arrange these chemistry things in increasing order of their nucleophilicity ? :D

RCOO- , RO- , ROH , RCOOH

1
Siddharth ·

Basicity F- > Cl- > Br- > I-
Leaving ability I- > Br- > Cl- > F-

Higher basicity, lower leaving ability

a nucleophile which has lower leaving ability will replace a nucleophile with higher leaving ability
a nucleophile which has higher nucleophilicity will replace a nucleophile with lower nucleophilicity.
a nucleophile which has higher basicity will replace a nucleophile with lower basicity

This is because more basic anion will have more negative charge on the nucleophilic atom. Eg. CH3OH is a stronger acid than C2H5OH because CH3O- is more stable than C2H5O- . (+I effect of C2H5 is more than CH3 group). Therefore C2H5O- is stronger base than CH3O- (Conjugate base of weaker acid is stronger). CH3O- has higher leaving ability than C2H5O-. C2H5O- has more electron density on O due to more +I effect compared to CH3O- .

11
Anirudh Narayanan ·

Well, unique. That maybe bcos CCl2 (or more formally :CCl2[3]) has two eletcrons less than the configuration it was comfortable with [1]

1
? ·

thats a unique thinking dude !!

then why is CCl2 a electrophile even though it has a lone pair of electrons ?

3
msp ·

when the electrostatic force of repulsion is greater the electrons have more tendency to get away from the atom because the electrostatic force is predominantly higher

1
Harry Potter ·

hey dai poyi urgan Unique Jinesh ..........nee poo monee dinesha..........

1
Harry Potter ·

hey dai poyi urgana ..........nee poo monee dinesha..........

1
? ·

"nucleophilicity or basicity arises when the electrostatic force of repulsion is greater than that of the electrostatic force of attraction"

can u elaborate this sankara ?

3
msp ·

i thot dat the discussion can be done by considering as ions.

nucleophilicity or basicity arises when the electrostatic force of repulsion is greater than that of the electrostatic force of attraction

please reply if i was wrong

3
msp ·

unique anna

in case of RCOO- the negative charge will be shared by the oxygen atom over a larger area which means dat the molecule is having a less charge per unit area

in case of RO- the charge on the oxygen atm is predominately higher and it will be like l

1
? ·

ha prateek !... its one and the same thing !!... well done buddies !!

shall we move on to another one ?

3
msp ·

PRATEEK I ALSO HAVE GIVEN THE SAME REASON

WE SHUD WAIT UNIQUES REPLY

1
Harry Potter ·

dai unique was my reason correct

1
? ·

sankara !!..thats very true !!

the O is just so mean to have the electrons with him !!... selfish girl ..hehe

so its rite sankara .........

1
prateek punj ·

wat about mine it can be one reason....

3
msp ·

please stop me if i blabbered

1
? ·

yes sankara but u have not written ROH in that ...please do check it !

1
Harry Potter ·

was my reason correct unique

3
msp ·

unique anna i have given the same ans
whle typing i have left the R letter

1
? ·

so any one like to reason it ?

1
prateek punj ·

might be due to resonance the charge on O gets delocalized and the charge is distributed among two O becoz of whcih the electron density decreases....
and therefore electron density of RO- greater as compared to RCOO-

3
msp ·

the nucleophilic atom was programmed to donate electrons

1
? ·

R-O- > R-COO- > R-OH > RCOOH

is the answer !

1
Harry Potter ·

becaz C0 bond is much more stronger than R0 bonds is that correct unique

1
prateek punj ·

can u please post the correct ans then we can discuss on it....

1
? ·

prateek i was just expecting this answer ... which is wrong !

but sankara what about the charge density on RCOO- ..why do u think it is less than that of RO- ?

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