Deck 21: Special Topic: Bio-Organic Chemistry

Question 1

What is the major product of the reaction of n-butyl bromide with excess ammonia?

A)butylamine
B)dibutylamine
C)tributylamine
D)tetrabutylammonium bromide
E)ammonium bromide

Answer 1

butylamine

Question 2

What is the major organic product of two-step transformation?

A)
B)
C)
D)
E)

Answer 2

Question 3

Which amine is the most basic?

A)

B)

C)

D)

E)

Answer 3

Question 4

Which of the following compound i s a lipid?

A)

B)

C)

D)

E)

Question 5

Which atom is the most basic in each molecule? Which of the molecules is more basic overall?

A)
B)
C)
D)
E)

Question 6

Which of the following compounds is an alkaloid?

A)
B)
C)
D)
E)

Question 7

Arrange the following amines in the order of increasing basicity.

A)
B)
C)
D)
E)

Question 8

What is the major cyclic product of the following reaction sequence?

A)

B)

C)

D)

E)

Question 9

Which class of the enzymes catalyzes the following reaction?

A) dehydrogenase
B) hydrogenase
C) peroxidase
D) oxidase
E) acyl transferase

Question 10

Which compound would not give butylamine as a major product upon reduction with LiAlH₄ ?

A) butanamide
B) butanenitrile
C) N-methylpropanamide
D) butyl azide
E) nitrobutane

Question 11

What is the final organic product of this two-step transformation?

A)
B)
C)
D)
E)

Question 12

What is the role of an iron-enzyme complex in the biochemistry of unsaturated fats?

A)Iron binds to the lipids, enhancing the membrane-permeation properties.
B)Iron complex catalyzes biosynthesis of lipids from acetyl-CoA.
C)Iron complex catalyzes oxidation of unsaturated lipids by oxygen.
D)all of the above
E)There are no known interaction between iron complexes and lipids.

Question 13

Which heterocycle is indole?

A)
B)
C)
D)
E)

Question 14

What is the product of the following reaction?

A)

B)

C)

D)

E)

Question 15

What is the major product of this reaction?

A)
B)
C)
D)
E)

Question 16

Which of the following statements about phospholipids is/are true?
I.Phospholipids contain a hydrophobic and a hydrophilic part in the molecule.
II)The polar part of the molecule is a sulfonic acid.
III)Phospholipids constitute an important part of cell membranes.
IV)Phospholipids form bilayers in water.

A)I
B)I, III
C)III, IV
D)I, III, IV
E)All of the above

Question 17

Which of the following compounds can be formed during catalytic hydrogenation of m-nitrobenzonitrile?

A) I
B) I, II, III
C) I, III, IV
D) II, III
E) I, II, III, IV

Question 18

Which alkaloid contains a tropane moiety?

A)
B)
C)
D)
E)

Question 19

Which of the following strutyres is isporene?

A)

B)

C)

D)

E)

Question 20

Which of these reactions directly leads to the formation of soap?

A)acidic hydrolysis of starch
B)enzymatic hydrolysis of starch
C)basic hydrolysis of fats
D)acidic hydrolysis of fats
E)amide bond formation between two amino acids

Question 21

What is the product of the following reaction?

Question 22

Which important class of bioorganic compounds is biosynthesized from arachidonic acid?

Question 23

Which important class of bioorganic compounds is produced by polycyclization of squalene?

Question 24

Rank the following compounds in order of increasing basicity.

Question 25

Provide the reagents necessary to achieve the following transformation.

Question 26

The following reaction sequence is part of a very important biosynthetic process related to the
synthesis of biomass.What is this process?

Question 27

What is the product of the following reaction?

Question 28

The following reversible transformation occurs in biological systems.
Draw the imine intermediate.

Question 29

What common heterocycle moiety is present in the structure of alkaloid morphine?

Question 30

Why the following synthesis of aniline does not work?

Question 31

Vegetable oil consists mainly of triglycerides of unsaturated fatty acids.Animal fat consists of
glycerol esters of saturated fatty acids.If stored in the presence of air and sunlight (and in the
absence of microorganisms), which type of fat is the most stable? Explain.

Question 32

Provide two different synthetic routes from X to Y:

Question 33

Dolichodial is synthesized in a biological system from two units of isoprene.

Two carbon atoms in isoprene were isotopically labeled with ¹³C (marked with *) and this molecule was introduced into the biosynthetic pathway. Which atoms in the resulting molecule of dolichodial will bear the ¹³C label?

Question 34

What is the product of the following reaction sequence?

Question 35

Typically, extraction of nonpolar organic compounds from biological materials is done with the
help of organic solvents.However, alkaloids, even the nonpolar ones, are often extracted from
plants by acidic aqueous solutions.Explain why this is possible.

Question 36

What common heterocycle moiety is present in the structure of alkaloid quinine?

Question 37

Rank the following compounds in order of increasing basicity.

Question 38

Which of the following lipids has the lowest melting point?

Question 39

Equal masses of stearic acid, polyalanine, and cellulose were combusted in pure oxygen.Which
compound has the largest heat of combustion?

Question 40

A mixture of three alkenes is formed in the following reaction sequence. The ratio of products is 67 (major): 27 (minor): 12 (trace). Identify each alkene and its abundance in the reaction mixture.