what makes a good nucleophile Flashcards

1
Q

Nucleophility along period 2

A

it decreases from carbon to f

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2
Q

why does nucleophility decrease along period

A

more electronegative elements hold their electrons more tightly, and are less able to donate them to form a new bond.

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3
Q

vertical periodic trend of nucleophility

A

The vertical periodic trend for nucleophilicity is somewhat more complicated that that for basicity: depending on the solvent that the reaction is taking place in, the nucleophilicity trend can go in either direction. Let’s take the simple example of the SN2 reaction below:

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4
Q

nucleophility down period 7 in protic solution

A

Relative nucleophilicity in a protic solvent increases

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5
Q

nucleophility down period 7 in polar aprotic solution

A

Relative nucleophilicity in a polar aprotic solvent decreases down the group

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6
Q

Resonance effects on nucleophilicity

A

If the electron lone pair on a heteroatom is delocalized by resonance, it is inherently less reactive - meaning less nucleophilic, and also less basic.

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7
Q

steric effect on nucleophility

A

Steric hindrance is an important consideration when evaluating nucleophility. For example, tert-butanol is less potent as a nucleophile than methanol. This is because the comparatively bulky methyl groups on the tertiary alcohol effectively block the route of attack by the nucleophilic oxygen, slowing the reaction down considerably

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