ch.7

Question 1

Sn2

Answer 1

nucleophilic attack, loss of a leaving group

Question 2

methyl

Answer 2

3 hydrogen attached to alpha carbon

Question 3

primary 1

Answer 3

2 hydrogen attached to alpha carbon

Question 4

secondary 2

Answer 4

1 hydrogen attached to alpha carbon

Question 5

tertiary 3

Answer 5

no hydrogens attached to alpha carbon

Question 6

strong nucleophiles

Answer 6

I, BR, Cl, HS, RS, HO, RO, CN

Question 7

weak nucleophiles

Answer 7

H2O, ROH

Question 8

Sn2 preferred solvent.

Answer 8

polar aprotic

Question 9

protic solvents

Answer 9

water, methanol, ethanol, ammonia, acetic acid

Question 10

polar aprotic solvents

Answer 10

Acetone, Dimethylsulfoxide (DMSO), Dimethylformamide (DMF), acetonitrile, Hexamethylphosphoramide (HMPA)

Question 11

protic solvents

Answer 11

H-bonding stabilize anions (like good nucleophiles) and also cations

Question 12

Aprotic solvents

Answer 12

stabilize cations only

Question 13

E2

Answer 13

proton transfer, loss of a leaving group

Question 14

Sn1

Answer 14

lose of a leaving group, nucleophilic attack (proton transfer)

Question 15

E1

Answer 15

loss of leaving group and proton transfer

Question 16

strong base; weak nucleophile (1-3)

Answer 16

E2

Question 17

strong base; strong nucleophile 1

Answer 17

E2 minor, Sn2 major

Question 18

strong base; strong nucleophile 2

Answer 18

E2 major; Sn2 minor

Question 19

strong base; strong nucleophile 3

Answer 19

E2

Question 20

weak base; strong nucleophile (1-2)

Answer 20

Sn2

Question 21

weak base; strong nucleophile 3

Answer 21

Sn1

Question 22

weak base; weak nucleophile (sterically hindered) 3

Answer 22

E1

Question 23

weak base; weak nucleophile (non-sterically hindered) 3

Answer 23

Sn1

Question 24

most stable to least stable carbocations

Answer 24

tertiary>secondary>primary>methyl

Question 25

least reactive to most reactive

Answer 25

I>Br>Cl>F

Question 26

water solvent type

Answer 26

protic

Question 27

ethanol solvent type

Answer 27

protic

Question 28

ammonia solvent type

Answer 28

protic

Question 29

acetic acid solvent type

Answer 29

protic

Question 30

acetone solvent type

Answer 30

polar aprotic

Question 31

DMF solvent type

Answer 31

polar aprotic

Question 32

HMPA solvent type

Answer 32

polar aprotic

Question 33

DSMO solvent type

Answer 33

polar aprotic

Question 34

acetonitrile solvent type

Answer 34

polar aprotic

Question 35

what is the major product for a substitution reaction with a sterically hindered substrate and sterically hindered base?

Answer 35

the less substituted alkane

Question 36

bredt's rule

Answer 36

a small bicyclo ring cannot have alkenes at the bridgeheads

Question 37

strong bases; weak nucleophiles

Answer 37

DBN;DBU

Question 38

strong bases; strong nucleophiles

Answer 38

OH-;EtO-;MeO-

Question 39

weak bases, strong nucleophiles

Answer 39

I; Br; Cl; RS; HS; RSH;

Question 40

weak bases, weak nucleophiles

Answer 40

H2O, MeOH, EtOH

Question 41

what does the rate of an Sn2 reaction depend on?

Answer 41

the strength of the nucleophile

Question 42

what does the rate of an E2 reaction depend on?

Answer 42

concentration of the alkyl halide and of the base

Question 43

what is the RDS for E1 and Sn1 reactions?

Answer 43

loss of a leaving group