Chapter 1 (E1)

Question 1

The notation used to draw organic molecules (also referred to as “line angle” or “zig zag”).

Answer 1

What is bond line?

Question 2

Any atom in a bond line structure that is not a C or an H.

Answer 2

What is a heteroatom?

Question 3

What is the typical order for a molecular formula?

Answer 3

CxHy, and then alphabetical order for the rest of the elements

Question 4

The “R” group in a chemical formula.

Answer 4

What is a generic alkyl?

Question 5

The “X” group in a chemical formula.

Answer 5

What is a halogen?

Question 6

The “Ph” group in a chemical formula.

Answer 6

What is phenyl?

Question 7

The part of a molecule where reactions occur.

Answer 7

What is a functional group?

Question 8

Electronegativity becomes greater as we move to the { } and { } on the periodic table (HINT: blanks are directions).

Answer 8

1) Right
2) Up

Question 9

Atomic radius/size becomes greater as we move to the { } and { } on the periodic table (HINT: blanks are directions).

Answer 9

1) Left
2) Down

Question 10

A ring containing one or more heteroatoms.

Answer 10

What is a heterocycle?

Question 11

The number of unsaturations in a molecule.

Answer 11

What is the index of hydrogen deficiency (IHD)?

Question 12

For every 1 unsaturation, how many hydrogens do we lose?

Answer 12

2

Question 13

Under what 2 molecular conditions do unsaturations occur?

Answer 13

1) Multi-bonds (i.e., double & triple)
2) Rings

Question 14

The mixing of atomic orbitals to form new hybrid orbitals.

Answer 14

What is hybridization?

Question 15

When does hybridization typically occur?

Answer 15

In preparation for bonding

Question 16

How many bonding areas (or areas of electron density) will you see with sp3 hybridization?

Answer 16

4

Question 17

How many bonding areas (or areas of electron density) will you see with sp2 hybridization?

Answer 17

3

Question 18

How many bonding areas (or areas of electron density) will you see with sp hybridization?

Answer 18

2

Question 19

A tetrahedral, sp3-carbon with 4 different groups attached.

Answer 19

What is a stereocenter?

Question 20

Non-superimposable mirror images.

Answer 20

What are enantiomers?

Question 21

What are the 4 rules for the Cahn-Ingold-Prelog (CIP) naming convention when assigning stereocenters?

Answer 21

1) Assign priorities from highest to lowest based on atomic number (1=highest priority)

2) If 2 groups have same priority, continue down chain until you see a difference

3) Visualize molecule so that lowest priority group is pointed away from you, then trace in a circle 1->2->3

4) For groups containing multi-bonds (i.e., double or triple bonds), assign priorities as if both atoms were duplicated or triplicated

Question 22

For Rule 3 of the CIP naming convention, a clockwise circle has an { } configuration.

Answer 22

R

Question 23

For Rule 3 of the CIP naming convention, a counterclockwise circle has an { } configuration.

Answer 23

S

Question 24

True or False: Enantiomers have identical physical properties.

Answer 24

True

Question 25

In what 2 ways do enantiomers differ from one another?

Answer 25

1) They show different interactions with other chiral molecules 2) They rotate plane-polarized light in opposite directions (i.e., optical activity)

Question 26

Does a negative sign correlate to a molecule being levorotary or dextrorotary?

Answer 26

Levorotary

Question 27

Does a positive sign correlate to a molecule being levorotary or dextrorotary?

Answer 27

Dextrorotary

Question 28

An instrument used to measure the optical activity of a chiral compound.

Answer 28

What is a polarimeter?

Question 29

Non-superimposable, non-mirror images, containing multiple stereocenters in which one or more, but not all, differ.

Answer 29

What are diastereomers?

Question 30

This plant was used in early China to treat coughs.

Answer 30

What is ma huang?

Question 31

What is the active ingredient in ma huang?

Answer 31

Ephedrine

Question 32

This Indian spice treats many ailments and is even used as a dietary supplement today.

Answer 32

What is turmeric?

Question 33

What is the active ingredient in turmeric?

Answer 33

Curcumin

Question 34

This Greek seed was a known analgesic.

Answer 34

What is the poppy seed?

Question 35

What is the active ingredient in poppy seeds?

Answer 35

Morphine

Question 36

This Peruvian tree bark is used to treat malaria and fever.

Answer 36

What is cinchona bark?

Question 37

What is the active ingredient in chinchona bark?

Answer 37

Quinine

Question 38

Are amino acids naturally L- or D-configured?

Answer 38

L

Question 39

Are sugars naturally L- or D- configured?

Answer 39

D

Question 40

How do you determine if a Fischer projection is L- or D-configured?

Answer 40

L-configured: chiral center's OH group on the left (NOTE: this only applies to the chiral center furthest from the C=O bond) D-configured: chiral center's OH group on the right (NOTE: this only applies to the chiral center furthest from the C=O bond)

Question 41

What birth defect did thalidomide cause?

Answer 41

Shortened limbs

Question 42

Which thalidomide enantiomer treated nausea?

Answer 42

R

Question 43

Which thalidomide enantiomer caused birth defects?

Answer 43

S

Question 44

How did S-thalidomide cause birth defects? What was the mechanism of action?

Answer 44

It prevented the growth of new blood vessels, particularly during the critical period of limb development early on in pregnancy

Question 45

Why did FDA medical officer Frances Kelsey deny thalidomide to be used in the U.S. for pregnant mothers?

Answer 45

There was not enough safety testing

Question 46

Why was there no point in isolating ONLY the R-thalidomide enantiomer?

Answer 46

It racemized in the body, so you would still end up with the S enantiomer

Question 47

What disease is thalidomide effective in treating today?

Answer 47

Multiple myeloma

Question 48

What does NSAID stand for?

Answer 48

Non-steroidal anti-inflammatory drug

Question 49

What does COX stand for?

Answer 49

Cyclooxygenase

Question 50

What is the relationship between COX enzymes, prostaglandin, pain, inflammation, and COX inhibitors?

Answer 50

COX enzymes produce prostaglandins, which are chemicals that cause pain and inflammation. COX inhibitors prevent the production of prostaglandins, thus preventing pain and inflammation

Question 51

Which 2 COX enzymes produce prostaglandins?

Answer 51

1 & 2

Question 52

Although acetaminophen is a COX-3 inhibitor, why is it not considered an NSAID?

Answer 52

Acetaminophen does not prevent inflammation, only pain and fever

Question 53

What is the serious side-effect of COX inhibitors?

Answer 53

Tightening of arteries, resulting in heart attacks and strokes

Question 54

Why was fen-phen removed from the market?

Answer 54

It caused pulmonary hypertension, often associated w/ heart valve problems

Question 55

What was the intended purpose of fen-phen?

Answer 55

Weight loss via amine-induced appetite suppression

Question 56

What medications was fen-phen a mixture of?

Answer 56

Either fenfluramine or dexfenfluramine mixed w/ phentermine