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Pharmacy (year one) > Synthesis of drugs > Flashcards

Synthesis of drugs Flashcards

1
Q

Is the hydrolysis of aspirin an addition or a substitution reaction?

A

Substitution

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2
Q

Acid chloride is unreactive because Cl- is a good leaving group. True or false?

A

False - it is very reactive

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3
Q

Are amides reactive or unreactive?

A

Very unreactive

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4
Q

NH2 can be used as a nucleophile and can react with any acid _______ or ________

A

chloride

anhydride

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5
Q

Ethanol doesn’t get excreted, it gets metabolised. It gets oxidised using ____________ to form acid aldehyde

A

alcohol dehydrogenase

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6
Q

Aldehyde dehydrogenase oxidises acid aldehyde to give ___________ which causes weight gain

A

acetic acid

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7
Q

Why is methanol toxic?

A

it is processed by alcohol dehydrogenase to give formaldehyde which causes death and blindness

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8
Q

Formaldehyde cannot be further processed as aldehyde dehydrogenases are much more specific than alcohol dehydrogenases. True or false?

A

True

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9
Q

What is used to treat methanol poisoning and ethylene glycol poisoning?

A

Whisky

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10
Q

ethanol -> acid aldehyde. Which enzyme is responsible for this oxidation?

A

alcohol dehydrogenase

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11
Q

acid aldehyde -> acetic acid. Which enzyme is responsible for this oxidation?

A

aldehyde dehydrogenase

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12
Q

Does alcohol dehydrogenase prefer to oxidise ethanol or non-ethanol alcohols?

A

ethanol

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13
Q

Is H- a good or bad leaving group?

A

Bad

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14
Q

Which is more reactive, acid chloride or acid anhydride?

A

chloride

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15
Q

which is more reactive amides or esters and COOH?

A

esters and COOH

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16
Q

The grignard reaction is a way of forming new _________ bonds

A

carbon-carbon

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17
Q

In the grignard reaction, what acts as the nucleophile?

A

carbon

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18
Q

The alpha carbon refers to which carbon?q

A

the carbon next to the carbonyl

19
Q

What is an e.g. of an alpha carbon reaction?

A

bromination of a carbonyl

20
Q

What type of reaction is most important for drug synthesis?

A

substitution

21
Q

What are the three types of reactions that carbonyls do?

A

substitution
addition
substitution at alpha carbon

22
Q

What are the possible leaving groups in nucleophilic substitution reactions?

A

Cl, Br, I, tosylate

23
Q

What is the biggest barrier for SN2 reactions?

A

steric hinderance - the more groups around the leaving group, the slower the rate of reaction

24
Q

In SN2 both the nucleophile and substrate are involved in the rate determining step. True or false?

A

True

25
Q

In a mechanism, what do square brackets and a sigma complex indicate?

A

A transition state

26
Q

In SN2 mechanisms, there is a complete racemisation at the carbon. True or false?

A

False - there is a complete inversion at the carbon

27
Q

How many steps are there in an SN2 reaction?

A

One step

28
Q

How many steps are there in an SN1 reaction?

A

Two steps

29
Q

If a leaving group is attached to an alkene or alkyne, will SN1 or SN2 reactions take place?

A

No - reactions only take place for alkyl halides

30
Q

What is the biggest barrier for SN1 reactions?

A

Stability of carbocation

31
Q

What happens in the first step of SN1 reactions?

A

Leaving group leaves upon which a carbocation is formed

32
Q

What happens in step 2 of SN1 reactions?

A

A nucleophile attacks the carbocation

33
Q

The carbocation intermediate in SN1 reactions is planar. True or false?

A

True

34
Q

In SN1 reactions there is complete racemisation at carbon. True or false?

A

True

35
Q

In SN1 reactions, only one side of the compound is accessible to the nucleophile. True or false?

A

False - both sides of compound are equally accessible to the compound

36
Q

In SN1 reactions, rate of reaction is dependent on the nucleophile. True or false?

A

False - it is independent - nucleophile is not involved in rate determining step

37
Q

What does acylation mean?

A

Adding a ketone group

38
Q

When a monosubstituted benzene reacts with an electrophile, substitution can be three things…

A

ortho
meta
para

39
Q

ortho is a 1,4 substitution. True or false?

A

False - it’s a 1,2 substitution

40
Q

1,4 substitution is called?

A

para

41
Q

What position is meta substitution?

A

1,3

42
Q

electron donating substituents give rise to which regioselectivity?

A

ortho

para

43
Q

electron withdrawing leads to which regioselectivity?

A

meta

44
Q

Which is more preffered, Friedel-Crafts acylation or alkylation?

A

acylation

Pharmacy (year one) (60 decks)

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