Chem test 3

Question 1

what is a stereoisomer?

Answer 1

a compound with the same chemical formula, but a different 3-dimensional arrangement of atoms. ( how they look in space)

Question 2

Why do we care about stereoisomers?

Answer 2

because they can have different effects in the body

Question 3

Thalidomide was a drug prescribed for morning sickness. After some research, they found that it was a mixture of _____

Answer 3

stereoisomers

Question 4

Drug companies have to prove to the FDA that a drug being proposed has either: (regarding stereoisomers)

Answer 4

single chemical entity, (one version of the stereoisomer) or
prove that both of the stereoisomers in the racemic mixture is safe

Question 5

what makes up a stereoisomer?

Answer 5

stereocenter/chiral center/stereogenic center
and either a enantiomer or diastereomer

Question 6

where a wedge or dash exists for this class, that is the

Answer 6

stereocenter

Question 7

What are the 2 types of stereoisomers

Answer 7

Enantiomers and diastereomers

Question 8

how do you know when you are dealing with a diastereomers?

Answer 8

all of their properties are different. They don’t have a lot incommon except their chemical formula and arrangement of atoms.

Question 9

what is the one property that is different in an enantiomer?

Answer 9

enantiomers are mirror images except for their optical rotation

Question 10

what is the optical rotation?

Answer 10

something that rotates polarized light
left (counterclockwise) is the negative direction
right (clockwise) is the positive direction

Question 11

in a stereocenter: for carbon atoms that only contain single bonds, there must be ______ different groups attached

Answer 11

4

Question 12

how to denote a stereocenter without a wedge or dash?

Answer 12

an asterisck

Question 13

which direction are solid wedges?
which direction are dashes?

Answer 13

in plane groups in: FRONT coming towards you
out of plane groups: BACK going away from you

Question 14

what are the rules to labeling stereocenters of a tetrahedral?

Answer 14

1. prioritize the atoms by increasing atomic number (look at the periodic table)
   *if 2 or more are the same, look at what they are attached to to find a point of difference.
2. Only consider atoms 1-3
   * if it is clockwise (to the right)=R stereoisomer
   * if is it counterclockwise (to the left= S stereoisomer
3. look at group 4.
   *if it is on the dash, the stereocenter is on the dash, keep it as it is
   *if it is on the wedge, invert the isomer.

Question 15

hydrogen always has the least ____ when labeling stereocenters

Answer 15

priority. The atomic number is 1, nothing is smaller than 1

Question 16

for carbons in an alkene, there must be two different groups attached to

Answer 16

each carbon of the double bond

Question 17

when labeling stereoisomers on alkenes, what are the naming options?

Answer 17

E=opposite side
Z=same side

Question 18

every double bond has a ____ carbon and a _____ carbon

Answer 18

left
right

Question 19

enantiomers can have 1 or more

Answer 19

stereocenters

Question 20

how to tell if you have an enantiomers in a picture of 2 structures?

Answer 20

all the stereocenters must be switched between 2 structures

Question 21

why can enantiomers impact how a compound interacts within the body?

Answer 21

the body recognizes the different stereocenter.

(i.e. spearmint vs. caraway seed smells)

Question 22

in a diastereomers you have to have a minimum of ____ stereocenters

Answer 22

2

Question 23

how to tell if you have an diastereomers in a picture of 2 structures?

Answer 23

one stereocenter changes and one stays the same (dash vs wedge)

Question 24

diastereomers structures are completely _______

Answer 24

different. Can even happen in different physical properties and have a liquid and a solid

Question 25

Enantiomer isomers usually involves one form that can be dangerous, usually diastereomers extra form doesn't really do

Answer 25

much of anything

Question 26

what is the standard aromatic compound?

Answer 26

Benzene

Question 27

heterocycles

Answer 27

a ring compound that contains a heteroatom

Question 28

The benzene ring is very _______

Answer 28

stable and common

Question 29

substituted benzine rings can have different names based on the

Answer 29

substituents attached to them

Question 30

Name this substituted benzene

Answer 30

toluene

Question 31

Name this substituted benzene

Answer 31

cumene

Question 32

Name this substituted benzene

Answer 32

styrene

Question 33

Name this substituted benzene

Answer 33

phenol

Question 34

Name this substituted benzene

Answer 34

anisole

Question 35

Name this di-substituted benzene

Answer 35

2-bromotoluene

Question 36

Name this di-substituted benzene

Answer 36

4-isopropylphenol

Question 37

Name this fused benzene

Answer 37

naphthalene

Question 38

Name this fused benzene

Answer 38

anthracene

Question 39

Name this fused benzene

Answer 39

phenanthrene

Question 40

Name this fused benzene

Answer 40

pyrene

Question 41

name this aromatic ring

Answer 41

benzene

Question 42

name this aromatic ring

Answer 42

pyrrole

Question 43

name this aromatic ring

Answer 43

furan

Question 44

name this aromatic ring

Answer 44

thiophene

Question 45

name this aromatic ring

Answer 45

imidazole

Question 46

name this aromatic ring

Answer 46

pyridine

Question 47

name this aromatic ring

Answer 47

pyrimidine

Question 48

name this aromatic ring

Answer 48

indole

Question 49

name this heterocycle

Answer 49

tetrahydrofuran

Question 50

name this heterocycle

Answer 50

pyrrolidine

Question 51

name this heterocycle

Answer 51

tetrahydropyran

Question 52

name this heterocycle

Answer 52

piperidine

Question 53

name this heterocycle

Answer 53

piperazine

Question 54

name this heterocycle

Answer 54

morpholine

Question 55

which drug class is this?

Answer 55

steroids

Question 56

which drug class is this?

Answer 56

quinines

Question 57

which drug class is this?

Answer 57

penicillins

Question 58

which drug class is this?

Answer 58

barbituates

Question 59

which drug class is this?

Answer 59

benzodiazepines

Question 60

which drug class is this?

Answer 60

anesthetics

Question 61

which drug class is this?

Answer 61

morphines

Question 62

which drug class is this?

Answer 62

bensomorphans

Question 63

which drug class is this?

Answer 63

phenylpiperidines

Question 64

Name this fused benzine

Answer 64

Fullerene AKA bucky Ball

Question 65

Name this functional group

Answer 65

Aldehyde

Question 66

Name this functional group

Answer 66

Ketone

Question 67

Name this functional group

Answer 67

Esters

Question 68

Name this functional group

Answer 68

Amide

Question 69

Name this functional group

Answer 69

Carboxylic acid

Question 70

Name this di-substituted benzene

Answer 70

3-methoxyaniline

Question 71

Name this substituted benzene

Answer 71

aniline

Question 72

Name this di-substituted benzene

Answer 72

3- methylstyrene

Question 73

steps to labeling an alkene stereoisomer:

Answer 73

1. find the stereocenter. this is where you have a double bond with 2 carbons. 2. Look at the right side and decide the priority 3. look at the left and decide the priority 4. draw a line through the double bond. If the priorities are both on the top or both on the bottom it is a Z isomer. If the priorities are on the opposite side then it is an E isomer.