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Medicinal Chemistry > Functional Group Chemistry 7 & 8 > Flashcards

Functional Group Chemistry 7 & 8 Flashcards

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1
Q

Describe amide stability

A

Very unreactive
More stable chemically than esters
L.P stabilised by resonance

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2
Q

What are the different types of amides?

A

Primary
Secondary
Tertiary

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3
Q

What are some important amides?

A

Paracetamol
Aspartame
Melatonin

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4
Q

What is the pKa of amides?

A

35

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5
Q

What are the properties of amides?

A

High B.Ps

Stable

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6
Q

What happens to B.Ps of liquids as intermolecular forces of solvent increase?

A

Increase

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7
Q

What is in amides?

A

H bonding

Strong dipole-dipole interactions

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8
Q

Describe amide structure

A

4 e- shared between 3 pi orbitals
N = planar = sp2
e- shared unequally = greater density in O

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9
Q

What does the amide have + why is it important?

A

Restricted rotation around amide bond

= gives rise to cis + trans orientations

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10
Q

How does solvents affect amides?

A

Rate of rotation is faster in least polar solvent

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11
Q

How are acid chlorides synthesised?

1

A

COOH + SOCl2 —-> CH3CH2CH2COOCl

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12
Q

What does an acid anhydride react with alcohol to form?

A

Ester + carboxylic acid

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13
Q

What does an acid anhydride react with H2O to form?

A

Carboxylic acid

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14
Q

What does an acid anhydride react with amine to form?

A

Amide + half of acid anhydride + 1 mole of amine

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15
Q

What is the equation for forming N-methylpropanamide?

A

Propanoic anhydride + 2 CH3NH2 —-> N-methylpropanamide + RNH3+ -OOCR

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16
Q

How do form an amide from an ester?

A

Ester + NH3 —-> Amide

17
Q

How do you go from an amide to an ester?

A

Amide + MeOH —-> Ester

18
Q

How do you form an amide from an acid?

A

COOH + RNH2 —-> Amide

Catalyst

19
Q

What is the strongest C=O?

A

Acid halide

= very weak delocalisation

20
Q

What is the weakest C=O?

A

Ester

= complete delocalisation

21
Q

What reagents are used for dehydration of amides to nitriles?

A

SOCl2
P2O5
POCl3

22
Q

What is the an acid chloride reduced to?

A

Amine

by LiAlh4

Medicinal Chemistry (19 decks)

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