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SL12101 Chemistry of drugs Y1 > Lecture 15 - Electrophilic carbonyls 2 > Flashcards

Lecture 15 - Electrophilic carbonyls 2 Flashcards

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1
Q

We can made esters from acyl chlorides. What are the reactants and products?

A

reactants: acyl chloride + alcohol
products: ester + HCl

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2
Q

Draw the mechanism for making an ester from an acyl chloride.

A
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3
Q

We can make esters from carboxylic acids. What are the reactants and products?

A

reactants: carboxylic acid + alcohol
products: ester + H+

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4
Q

Esters can be made from carboxylic acids as well as acyl chlorides. But, carboxylic acids are not very reactive so under what conditions does the reaction occur?

A

Acid catalyst- this protonates the carbonyl oxygen

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5
Q

Draw the mechanism for the production of an ester from a carboxylic acid

A
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6
Q

We can make amides from acyl chlorides. What are the reactants and products?

A

Reactants: acyl chloride + amine
Products: amides + HCl

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7
Q

Draw the mechanism for making an amide from an acyl chloride

A
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8
Q

Amides can be made from carboxylic acids. What are the reactants and products?

A

reactants: carboxylic acid + amine
product: ammonium carboxylate salt.

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9
Q

Draw reaction for making an amide from carboxylic acid

A
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10
Q

Nature makes amide bonds. Draw the mechanism for the production of glutamine from glutamate.

A
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11
Q

Acyl phosphate structure

A
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12
Q

What is a hydrolysis reaction?

A

a reaction where a molecule of water breaks one or more chemical bonds.

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13
Q

Acidic hydrolysis of an ester produces…

This is a fully …………… reaction

A

carboxylic acid and alcohol

reversible

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14
Q

Draw the mechanism for the acid hydrolysis of an ester.

A
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15
Q

Basic hydrolysis of an ester produces….

A

carboxylate ion and alcohol

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16
Q

Draw the mechanism for the base hydrolysis of an ester.

A
17
Q

Why is the hydrolysis of amides so difficult?

A

They are the least reactive.

18
Q

Acid hydrolysis of an amide produces…

A

carboxylic acid and ammonia

19
Q

Draw the mechanism for acidic amide hydrolysis

A
20
Q

Base hydrolysis of an amide produces…

A

carboxylate and ammonia

21
Q

Draw the mechanism for basic amide hydrolysis

A
22
Q

Hydrolysis of an ………… is easier than ……………

A

ester
amide

SL12101 Chemistry of drugs Y1 (20 decks)

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