Lecture 8: Chemistry of Haloalkanes (Nucleophilic Substitution)

Question 1

types of reactions of haloalkanes

Answer 1

1. alkane + halogen —> free radical substitution
2. alkene + HX —> electrophilic addition

Question 2

whats the strongest CX bond?

Answer 2

C and Fluorine

Question 3

2 pathways for nucleophilic substitution

Answer 3

SN1 & SN2

Question 4

SN1 characteristics

Answer 4

1. longer
2. rate depends on haloalkane only
3. enantiomers formed in equal amounts
4. tertiary haloalkane means SN1 favored
5. mechanism contains carbocation

Question 5

SN2 characteristics

Answer 5

1. shorter
2. rate depends on nucleophile and haloalkane
3. only one product
4. less sterically hindered means SN2 favored

Question 6

SN1 mechanism steps

Answer 6

1. CX bond to X-
2. carbocation formed
3. Nu- ro carbocation
4. X- left outside
5. Nu substituted

Question 7

SN2 mechanism steps

Answer 7

1. Nu to C in CX
2. CX bond to X
3. Nu substituted