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Chem > Organic :( > Flashcards

Organic :( Flashcards

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1
Q

Nucleophilic addition HOMO?

A

Nucleophile lp

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2
Q

NA LUMO?

A

C=O pi*

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3
Q

NA hard or soft nucleophile?

A

Hard (electrostatic attraction important)

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4
Q

NA mechanism

A

See notes

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5
Q

What is the Burgyl-Dunitz trajectory?

A

approach of nucleophile 107 degrees to c=o bond

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6
Q

Draw out reasons for ideal angle of nucleophile approach

A

See notes

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7
Q

Large bulky R groups effect on reactivity

A

Reduced, increase steric crowding

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8
Q

e- withdrawing groups effect on reactivity

A

higher, increase electrostatic attraction

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9
Q

water reacts with HCOCCl3 mechanism

A

see notes

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10
Q

RC=OR’ (NaCN, EtOH) -> R’RC(CN)(OH)

A

see notes

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11
Q

NaHSO3 nucleophilic attack draw mechanism

A

see notes

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12
Q

Addition of hydride to carbonyl what is source of nucleophilic hydrogen?

A

B-H or Al-H bonds

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13
Q

HOMO and LUMO hydride addition?

A

HOMO BHsigma LUMO C=O pi*

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14
Q

Draw general hydride addition reaction

A

see notes

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15
Q

Hydride: aldehydes reduced to…

A

primary alcohol

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16
Q

Hydride: ketones reduced to…

A

secondary alcohol

17
Q

Speed of aldehyde vs ketone reduction?

A

aldehyde faster, less steric crowding, less sigma donation

18
Q

Most convenient hydride reagent?

A

NaBH4 - reduces aldehydes and ketone ONLY (mildest reagent for job)
Reactions often carried out in protic solvent so can be source of >1 hydride so less than 1 equivalent can be used

19
Q

In organometallic reagents c-metal bond is…

A

polarised towards carbon so carbon is a nucleophilic centre

20
Q

How do you prepare Grignard reagent?

A

see notes

21
Q

How do you prepare organolithium?

A

see notes

22
Q

R-metals…

A

are powerful carbon nucleophiles, attack carbonyl groups of aldehydes/ketones to make alcohols (and form new C-C bond!)

Chem (6 decks)

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