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review Flashcards

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1
Q

Electrophile

A

molecules that accept electrons to form a new bond

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2
Q

What charges do electrophiles have?

A

positive or partially positive charge

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3
Q

R1 and R2 directly bound to the carbonyl could affect what?

A

Electrophilicity

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4
Q

What ways could R1 and R2 affect the carbon’s electrophilicity?

A

if R1 or R2 donates an electron density, then the carbons is less electrophilic

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5
Q

What are the two ways that R1 and R2 could affect electrophilicity?

A

Resonance and Hyperconjugation

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6
Q

Resonance

A

delocalization of electron within a certain molecule

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7
Q

Hyperconjugation

A

a weak overlap between p orbital in the carbonyl carbon and sp3 in the ch3 group. Usually happens between c-c or c-h groups. (very week electron donation).

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8
Q

Could aldehydes have resonance or hyperconjugation?

A

No (best electrophile)

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9
Q

Could ketones have resonance or hyperconjugation

A

No resonance but can undergo hyperconjugation

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10
Q

Could esters have resonance or hyperconjugation

A

Yes (least electrophile)

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11
Q

Nucleophile

A

a molecule that donates electron density to an electrophile so as to form a new bond

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12
Q

what charges are the nucleophiles

A

negative or partially negative

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13
Q

How do nucleophiles react with electrophiles

A

they attack the carbonyl carbon making the π electrons to be pushed to oxygen

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14
Q

What are the two types of additions

A

reversible and irreversible

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15
Q

What happens during a reversible addition

A

Nucleophile attacks and a weak bond is formed that could usually go backward (reverse). Usually, the nucleophile used is weak

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16
Q

What happens during irreversible addition

A

Nucleophile attacks and a strong bond that can’t go reverse (backward) is formed. Usually, a strong and reactive nucleophile is used.

17
Q

what are the two types of irreversible additions

A

organometallic reagents and hydride reagent

18
Q

What is an organometallic reagent

A

This is a carbonion with a metallic countercation

19
Q

What are the two types of Organometallic reagents

A

Organolithiums (Li) and Grignard reagents (MgBr)

20
Q

How do organometallic reagents react with carbonyls

A

Step 1 is the addition of the R organometallic reagent with ethereal solvent and step2 you add H+

21
Q

What shape do the carbonyl carbons changes from and to after the addition of organometallic reagents

A

From sp2 to sp3

22
Q

Why should we always make sure that in organometallic reaction the rxn is anhydrous?

A

since water is an acid and also a base, it could react with carbonyl to form an acid-base rxn. deprotonation rxn usually kills the nucleophiles. This why H+ is added at the second step of the rxn.

23
Q

What is a hydride reagents

A

additions of hydrides (H-) which a very strong and a reactive nucleophile to electrophiles

24
Q

what are the two types oh hydride reagents

A

Sodium borohydride (NaBh4) and lithium aluminum hydride(LAH)

25
Q

What electrophiles do both nabh4 and lah react with

A

aldehydes and ketones

26
Q

what are two differences between lah and nabh4

A
  1. nabh4 uses a solvent as proton source(MEOH OR ETOH) while lah uses H+ as a proton source in which u add it at the second step.
  2. Lah is more nucleophilic and basic than nabh4
27
Q

what are hydride reactions usually referred to?

A

reduction. This is because the number of bonds to oxygen has been reduced.

28
Q

What is the difference between hydride rxn and an organometallic rxn

A

in hydride rxns, we don’t add any new carbon element in the rxn but in organometallic rxns, we add carbon elemets

29
Q

why is it that nabh4 can react with esters and carboxylic acids

A

This is because nabh4 is a weak nucleophile and since both esters and carboxylic acids are weak electrophiles, they need a strong nucleophile to react.
That is why we use Lah to reduces them

30
Q

what do we call the reactions in which nucleophiles displace a leaving group in an alkyl electrophile?

A

SN1 and SN2

31
Q

what do sn1 and Sn1 stand for?

A

substitution nucleophilic (bimolecular or unimolecular)

organic chem (1 decks)

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