In the ACS book pg 73 2006 edition, it states that the nitrogen atom is inherently much better nucleophile (more powerful base) than the oxygen atom and also preferentially strikes the carbonyl carbon atom. Why is the nitrogen a better nucleophile? isn"t the oxygen a better electron withdrawing atom than the nitrogen?
because O is even more electronegative then N, the electron deserve to be held stronger in the O then in the N. therefore, it will certainly be harder to form O nucleophile then N nucleophile.

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poc91nc
I think the line of thinking for why N is a much better nucleophile is because nitrogen is bigger than oxygen. Thus, the external electrons are held even more loosley and also even more easily donated (as a nucleophile/lewis base). Electronegativity doesn"t explain why Nitrogen is a better nucleophile b/c nitrogen is to the ideal of oxygen. Electronegativity rises left to right. N|O This same line of thinking explains why R-S:- is a much better nucleophile than R-O:- (alkoxide)
jdoc04
N (-3) charge provides it a more powerful nucleophile than O (-2). What does a nucleophile like??.............Hopeful charges therefore N is more strongly attracted to a electrophile (+). Nitrogen is not even more EN than O nor is it larger. EN increases Left to Right throughout a period and also up a team N- MW 14 O- MW 16 I hope this helps!!
ok i acquired it. since O is more electronegative then N, the electron can be hosted stronger in the O then in the N. thus, it will be harder to form O nucleophile then N nucleophile.
I think Poc91nc reasoning is correct bigger atoms=loosely held electrons. Nucleophiles are electron wealthy and also desire to donate the electrons, and also the loosely organized electrons are simpler to provide up making them the best nucleophiles
War Eagle
Last I checked on a table N is smaller sized than O. The real reason has actually been declared currently. N is less electronegative, therefore its electrons are hosted more loosely and also deserve to react more easily through other molecules. You have the right to also think of it in the terms that even more electronegative atoms manage an adverse charge better (F is even more most likely to have a negative charge than C). Due to the fact that N isn"t as electronegative as O, it doesn"t bring the negative charge also and is even more reenergetic.

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poc91nc
Last I checked on a table N is smaller than O
. The real factor has actually been proclaimed currently. N is less electronegative, therefore its electrons are organized more loosely and also can react more conveniently with other molecules. You can also think of it in the terms that even more electronegative atoms take care of a negative charge better (F is more likely to have actually an unfavorable charge than C). Because N isn"t as electronegative as O, it does not bring the negative charge as well and is more reactive.
War Eagle, Could you please verify your claim? For primary group elements, size ALWAYS rises from RIGHT to LEFT. As you go appropriate to left EN decreases too. Therefore, decreasing electronegativity ALWAYS parallels size for the main group elements. Which comes initially...chicken or the egg? So...does dimension not contribute to exactly how loosley the outer electrons are held? Is electronegativity a manifesation of size? or vice versa? Nitrogen is to the left oxygen on the routine table. If you still don"t believe me: pg 309 of Chemistry by Silberberg number 8.12 atomic radii of nitrogen 75 atomic radii of oxygen 73
poc91nc
N is LARGER than O. It has actually much less protons which subsequently holds the valence electrons less loosely providing it a larder atomic radius than O which has more proloads. N is additionally much less electronegative than O, what I should have actually shelp is that for me it is most basic to think of the best nucleophile as one that can easily give ameans electrons aka the bigger atom
If size rises...electronegativity decreases. So, is nitrogen less electronegative b/c it is larger, or is nitrogen larger b/c it is much less electronegative? That is what I am puzzled around....which describes which? dimension or electronegativity....chicken or egg?
I think what helps most is understanding the meanings of both electronegativity and atomic size. All the periodic trends relate to each other in some way so it just counts on how you look at it. Electronegativity
= the capacity an atom has to tempt electrons so Flourine the smallest facet to the appropriate of the routine table desires that additional electron to make it a noble gas. The little size right here is among the reason electronegativity is so high because it alows the flourine atom to pull the electrons cshed to it. Atomic Size: How huge an atom is So significant atoms have actually much ameans electrons that are held loosely (akan interpretation of weak electronegativity) Nucleophilicity=electron well-off species which will provide its electrons to electrophiles "electron loving" species Aget for me I personally think it is less complicated to look at big atoms as the finest nucleophiles bereason large atoms have the right to conveniently offer ameans electrons which is what a nucleophile wants to carry out. You can think of it as weak electronegativity however for me I think of electronegativity as something to carry out with stamina of bonding