Amines and amides

Question 1

How does chloroquine cure malaria?

Answer 1

• Concentrates in the acidic food vacuole as it is basic so moves down conc. gradient
• Forms complexes with the haematin and disrupts hemozoin formation
• Prevents removal of haem

Question 2

What adaption from malaria parasites has led to resistance to choloroquine?

Answer 2

Up-regulation of transporters that pump chloroquine out of the food vacuole

Question 3

Is the electronegativity of O greater than N?

Answer 3

Yes

Question 4

What is the orbital structure of amines?

Answer 4

4sp³ hybridized

Question 5

What shape are amines?

Answer 5

Trigonal pyramidal

Question 6

What is the bond angle of amines?

Answer 6

Around 107º

Question 7

Compare the basicity of aromatic and aliphatic amines

Answer 7

Aromatic amines are less basic than aliphatic amines

Question 8

What is the approximate pKa of aromatic amines?

Answer 8

4-5 (conj)

Question 9

Why are aromatic amines less basic?

Answer 9

Withdrawl of nitrogen lone pair via delocalisation

Question 10

Which carbon does ortho refer to?

Answer 10

2/6

Question 11

Which carbon does meta refer to?

Answer 11

3/5

Question 12

Which carbon does para refer to?

Answer 12

4

Question 13

Give 4 examples of electron donating groups

Answer 13

• CH₃
• OH
• NH₂
• HS

Question 14

Give 2 examples of electron withdrawing groups

Answer 14

• NO₂
• Br

Question 15

Does a higher pKa mean a compound is more basic?

Answer 15

Yes

Question 16

Give a way of synthesizing amines, what is a problem with this method?

Answer 16

Amine alkylation, often results in a mixture of amines

Question 17

Can amines hydrogen bond?

Answer 17

Yes

Question 18

What is the reaction of primary amines with activated esters used for?

Answer 18

Used to couple proteins to affinity matrices for chromatography or cross-linking proteins

Question 19

What function groups are present in amides?

Answer 19

Amine and carboxyl

Question 20

What orbital structure does the carbonyl group in amides take?

Answer 20

3sp² hybrid orbitals and one unchanged p-orbital which lies at right angles to the plane of the hybrid orbitals

Question 21

How are amides formed?

Answer 21

By condensationof carboxylic acids with amines

Question 22

How are amides synthesized chemically?

Answer 22

Acid anhydride mixed with an amine to produce a carboxylic acid and an amide

Question 23

Compare the relative basicity of amines and amides

Answer 23

Amides are much less basic than amines

Question 24

How can a protein being produced by a bacteria by quickly isolated?

Answer 24

• On gene for protein add code for a row of 6 histidine amino acids
• put protein through column
• No other protein in nature has 6x His in a row
• His tail sticks to column due to coordinate bonds with Ni²⁺ in column