CH8 Mechanisms Flashcards

1
Q

Define mechanism

A

Shows how a reaction occurs. Demonstrates how an electron flows.

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2
Q

Name the 3 types of mechanisms

A

Ionic, Radical, and Pericyclic.

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3
Q

Key for demonstrating electrons (find what and go towards what)

A

Find the most negative/partial negative souce and use that to go towards the most positive/partial positive source.

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4
Q

Define nucleophile

A

Ion or compound that is capable of donating a pair of electrons
*Must had a pi bond or lone pair(s)

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5
Q

Define electrophile

A

Ion or compound poor in electron density and want electrons.

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6
Q

Define Basicity and what makes a base strong/weak

A

Basicity is the measure of the position of equilibrium of an acid/base reaction.
A strong base = donate electrons quickly, picks up H+ quickly
A weak base = donate electrons slowly, picks up H+ slowly.

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7
Q

Define nucleophilicity and what makes a strong/weak nuc?

A

Nucleophility is how quickly a nuc will attack.
A strong nuc attacks fast, but a weak one reacts slow.

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8
Q

Define a proton transfer

A

Transfer of H is fast and happens first.

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9
Q

What makes something a strong nuc and a strong base?

A

Can donate electrons easily and pick up protons easily.

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10
Q

What makes something a weak nuc and a weak base?

A

Does not donate electrons easily or pick up protons easily

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11
Q

What makes something a strong nuc and a weak base?

A

Donates electrons easily but does not pick up protons easily.

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12
Q

What makes something a weak nuc and strong base?

A

Pick up protons easily but does not donate electrons easily.

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13
Q

Define polarizable

A

Electron density can shift more easily in response to external influence due to size. Polarizable makes a good nuc.

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14
Q

Define Carbocations

A

Unstable, high energy, short-lived intermediates that can be rearranged to low energy intermediates.

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15
Q

What are the 2 types of resonance stabilized carbocations?

A

Allylic carbocation and Benzylic carbocation

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16
Q

Define hydride shift

A

Moving a hydrogen from an adjacent carbon to where the carbocation is to stabilize charge.

17
Q

Define methyl shift

A

Moving a methyl group from an adjacent carbon to where the carbocation is.

18
Q

What are the 5 rearrangement mechanisms and their shorthand names?

A

Nucleophilic Attack (NA)
Proton Transfer (PT)
Loss of Leaving Group (LLG)
Rearrangement (REAR)
Resonance (RES)

19
Q

What does NA do?

A

Nuc attaches to an electrophile.

20
Q

What does PT do?

A

“stealing” of a proton/hydrogen. A subcategory of NA.

21
Q

What does LLG do?

A

Bond breaks and turns into a lone pair, severing a connection in the molecule.

22
Q

What does REAR do?

A

Rearrangement of a molecule (shifting of methyl, etc)

23
Q

What does RES do?

A

Technically not a mechanism. Movement of electrons in the molecule.