Chapter 5

Question 1

isomer

Answer 1

nonidentical molecules that have the same formula

Question 2

constitutional isomer

Answer 2

same molecular formula but a different order of connectivity of atoms

Question 3

stereoisomers

Answer 3

same molecular formula and constitution but a different spatial arrangement

Question 4

regioselectivity

Answer 4

determines the position within a molecule a reaction occurs, guiding which region or direction is favored

Question 5

stereoselectivity

Answer 5

focuses on the spatial arrangement of atoms, leading to the preferential formation of one stereoisomer over others

Question 6

regioselectivity is about ________ a reaction happens on a molecules, while stereoselectivity is about ___________ atoms are arranged in the resulting product

Answer 6

“where”, “how”

Question 7

geometric isomers

Answer 7

cis and trans

Question 8

chiral atoms

Answer 8

bonded to 4 DIFFERENT groups of atoms

Question 9

enantiomers

Answer 9

non-superimposable mirror images (all stereo centers switch)

Question 10

diastereomers

Answer 10

stereoisomers, but NOT mirror images (cis and trans)
(at least one (but not all) stereo centers switch)

Question 11

Cohn-Ingold-Prelog Rules

Answer 11

1. identify chiral atom (4 different groups)
2. assign priority by atomic number
3. tie = take a step out
4. rotate so that priority 4 is in the back
5. determine R vs S

Question 12

R configuration

Answer 12

clockwise

Question 13

S configuration

Answer 13

counterclockwise

Question 14

2^n

Answer 14

• equation to determine the maximum number of stereoisomers
• n=chiral centers