Synthesis of drugs

Question 1

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

Answer 1

Substitution

Question 2

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

Answer 2

False - it is very reactive

Question 3

Are amides reactive or unreactive?

Answer 3

Very unreactive

Question 4

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

Answer 4

chloride

anhydride

Question 5

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

Answer 5

alcohol dehydrogenase

Question 6

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

Answer 6

acetic acid

Question 7

Why is methanol toxic?

Answer 7

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

Question 8

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

Answer 8

True

Question 9

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

Answer 9

Whisky

Question 10

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

Answer 10

alcohol dehydrogenase

Question 11

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

Answer 11

aldehyde dehydrogenase

Question 12

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

Answer 12

ethanol

Question 13

Is H- a good or bad leaving group?

Answer 13

Bad

Question 14

Which is more reactive, acid chloride or acid anhydride?

Answer 14

chloride

Question 15

which is more reactive amides or esters and COOH?

Answer 15

esters and COOH

Question 16

The grignard reaction is a way of forming new _________ bonds

Answer 16

carbon-carbon

Question 17

In the grignard reaction, what acts as the nucleophile?

Answer 17

carbon

Question 18

The alpha carbon refers to which carbon?q

Answer 18

the carbon next to the carbonyl

Question 19

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

Answer 19

bromination of a carbonyl

Question 20

What type of reaction is most important for drug synthesis?

Answer 20

substitution

Question 21

What are the three types of reactions that carbonyls do?

Answer 21

substitution
addition
substitution at alpha carbon

Question 22

What are the possible leaving groups in nucleophilic substitution reactions?

Answer 22

Cl, Br, I, tosylate

Question 23

What is the biggest barrier for SN2 reactions?

Answer 23

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

Question 24

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

Answer 24

True

Question 25

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

Answer 25

A transition state

Question 26

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

Answer 26

False - there is a complete inversion at the carbon

Question 27

How many steps are there in an SN2 reaction?

Answer 27

One step

Question 28

How many steps are there in an SN1 reaction?

Answer 28

Two steps

Question 29

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

Answer 29

No - reactions only take place for alkyl halides

Question 30

What is the biggest barrier for SN1 reactions?

Answer 30

Stability of carbocation

Question 31

What happens in the first step of SN1 reactions?

Answer 31

Leaving group leaves upon which a carbocation is formed

Question 32

What happens in step 2 of SN1 reactions?

Answer 32

A nucleophile attacks the carbocation

Question 33

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

Answer 33

True

Question 34

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

Answer 34

True

Question 35

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

Answer 35

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

Question 36

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

Answer 36

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

Question 37

What does acylation mean?

Answer 37

Adding a ketone group

Question 38

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

Answer 38

ortho meta para

Question 39

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

Answer 39

False - it's a 1,2 substitution

Question 40

1,4 substitution is called?

Answer 40

para

Question 41

What position is meta substitution?

Answer 41

1,3

Question 42

electron donating substituents give rise to which regioselectivity?

Answer 42

ortho | para

Question 43

electron withdrawing leads to which regioselectivity?

Answer 43

meta

Question 44

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

Answer 44

acylation