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Medicinal Chemistry > Carbonyls 2 > Flashcards

Carbonyls 2 Flashcards

1
Q

What are aldehydes oxidised to?

A

COOH

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2
Q

What oxidising agents are used?

A

CrO3
KMnO3
HNO3

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3
Q

What is ethinylestradiol used in?

A

Formulation of combined pill

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4
Q

What is required in ethinylestradiol?

A

NaNH2

Liquid NH3

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5
Q

Why do all COOH derivatives react by same mechanism?

A

Polarity of carbonyl group

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6
Q

What happens in nucleophilic acyl substitution?

A

Nu- adds carbonyl carbon
= forms tetrahedral anionic intermediate
Leaving group expelled
Tetrahedral intermediate eliminated weakest base

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7
Q

When is Nu- expelled and why?

A

Nu- weaker than leaving group

= Nu- more stable than L-

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8
Q

When is L- expelled and why?

A

L- weaker than Nu-

= leaving group more stable than Nu-

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9
Q

Which intermediate will decompose the fastest?

A

One with best leaving group

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10
Q

What happens to reactivity as leaving group becomes more basic?

A

Decreases

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11
Q

Why is a WB more electronegative?

A

Able to accommodate negative charge better

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12
Q

Why is a WB better at inductive e- withdrawal from carbonyl C?

A

Increases electrophilicity of carbonyl carbon
More electrophilic carbonyl groups = more reactive to addition
Carbonyl carbon more susceptible to nucleophilic attack

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13
Q

Are acid halides more reactive than amides?

A

YES

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14
Q

Why is chloride good leaving group?

A

Undergoes acyl substitution easy

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15
Q

Is chloride useful in pharmaceutics?

A

Too reactive

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16
Q

What do you need to synthesise acid chlorides?

A

COOH + SOCl2 (thionyl chloride)

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17
Q

What reactions can acid chlorides undergo?

A

Nucleophilic acyl substitution
Hydrolysis
—-> ester/amides

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18
Q

What happens in nucleophilic substitution of acid chloride?

A

Follows general mechanism

Halogen replaced by OH, OR, OC(=O)R or NH2

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19
Q

What is formed acid chloride + NH3?

A

Amide

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20
Q

What is formed acid chloride + R’OH?

21
Q

What is formed acid chloride + R’CO2-?

A

Acid anhydride

22
Q

What is formed acid chloride + H2O?

A

Carboxylic acid

23
Q

What is does acid chloride hydrolysis form?

24
Q

What happens in acid chloride hydrolysis?

A

Add H2O

Tetrahedral intermediate undergoes elimination of Cl- + loss of H+ to give COOH

25
Q

What is formed acid chloride + alcohol?

26
Q

What is formed acid chloride + NH3?

A

Primary amide

27
Q

What is formed acid chloride + RNH2?

A

Secondary amide

28
Q

What is formed acid chloride + R2NH?

A

Tertiary amide

29
Q

What must be present to form ester from acid chloride?

A

Presences of tertiary amine base
OR
NaOH

30
Q

What reactions can acid anhydrides undergo?

A

—-> esters

31
Q

What does acetic anhydride form?

A

Acetate ester

32
Q

Are anhydrides less reactive than acid chlorides?

33
Q

What reactions can esters undergo?

A

Transesterification
Aminolysis
Reduction

34
Q

What happens in transesterification?

A

Alkoxy group replaced by another with acid or base catalyst

35
Q

What is required in transesterification?

A

Large excess of alcohol

36
Q

What happens in aminolysis?

A

NH3, primary amine or secondary amine react to form amide

37
Q

What is the equation for aminolysis?

A

RCOOEt + NH3 —-> RCONH2 + EtOH

38
Q

What happens in reduction of esters?

A

Yields 2x = aldehyde the primary alcohol

39
Q

What is required in reduction of esters?

40
Q

What is Xenical (active orlistat)?

A

Anti-obesity drug

41
Q

Where does Xenical work?

A

Locally in stomach + small intestine

42
Q

What does Xenical prevent?

A

Action of gastric + pancreatic lipases

43
Q

How does Xenical work?

A

Irreversible acylation of active site serine in phospholipase
Inactive enzyme cannot hydrolyse triglyceride = block fat uptake

44
Q

What is acetylcholinesterase responsible for?

A

Nerve-impulse transmission

45
Q

What is the second site of reactivity for aldehydes, ketones, esters + N,N-disubstituted amides?

A

Alpha H

= acidic enough to be removed by strong base

46
Q

In reaction elonate ions + enols what does the reaction at C or O depend on?

A

Electrophile + reaction conditions

47
Q

Where does protonation normally occur in reaction of elonate ions + enols?

48
Q

What is the consequences of enolization?

A

Stability

Racemization = any chiral centre next to carbonyl prone to racemization

49
Q

What happens when alpha carbon is halogenated?

A

Electrophilic

Medicinal Chemistry (19 decks)

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