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B18OB > Dr Barker > Flashcards

Dr Barker Flashcards

1
Q

EWG ___ hydration

A

Promote

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2
Q

EDG ___ hydration

A

Inhibt

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3
Q

Relative reactivities at C=O

A

Acid chloride, anhydride, aldehyde, ketone, ester, amine

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4
Q

EWG ___ acidity

A

Increase = lower pKa gives more stable anion

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5
Q

EDG ___ acidity

A

Decreases = higher pKa so less stable anion

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6
Q

How are enolates stabilised

A

Resonance stabilised by delocalisation of negative charge onto oxygen

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7
Q

Why is LDA a good base

A

Very sterically hindered so is a poor nucleophile

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8
Q

When are crossed aldol reactions successful

A

Only one carbonyl has enolisable alpha-H and the non-enolisable carbonyl compound is more electrophilic

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9
Q

Use of reformatsky reaction

A

React with aldehydes and ketones but not ester so no danger of self reaction

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10
Q

Claisen produces

A

1,3-dicarbonyls with ester group

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11
Q

What does final step of Claisen require

A

irreversible deprotonation

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12
Q

What’s Robinson annulation

A

Michael addition followed by intramolecular aldol condensation

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13
Q

Robinson annulation produces

A

6 membered rings

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14
Q

What base is needed to deprotonate phophonium salts

A

nBuLi

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15
Q

How are ylides formed

A

PPh3 and alkyl halide

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16
Q

Stabilised ylides

A

Have another group to stabilise eg C=O or CN

17
Q

What to stabilised ylides produce

A

E/trans alkenes

18
Q

What base s needed to deprotonate stabilised ylides

A

NaOEt

19
Q

What do unstabilised ylides give

A

Z/cis alkenes

20
Q

Can unstabilised ylides be stored

A

No

21
Q

compare reactivity of stabilised and unstabilised ylides

A

Stabilised only react with aldehydes and unstabilised react with aldehydes and ketones

22
Q

What does aldol condensation produce at a) low temps and b) high temps

A

A) β-hydroxycarbonyl
B) E1cB removal of water gives enal

23
Q

Prep of organocopper reagents

A
  1. Alkyl halide and lithium gives alkyl lithium
  2. 2 x alkyl lithium and CuI in ether gives organocopper and lithium salt
24
Q

Product of tandem conjugate addition of cuprate

A

Alkyl groups installed trans due to sterics and needs reactive alkylation agents eg non-sterically hindered alkyl bromides

25
Q

What’s needed to reduce aldehydes and ketones

A

NaBH4

26
Q

What’s needed to reduce esters and amines

A

LiAlH4

27
Q

Carboxylic acid and alcohol gives

A

Ester and water, reversible reaction

28
Q

Alcohol and acid chloride/ anhydride

A

Gives carboxylic acid

29
Q

Reformatsky and carbonyl gives

A

β-hydroxyester at low temps or enone at high temps

B18OB (4 decks)

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