212 Chem Alkyl halide problems 3
Provide the products for the following reactions, show the mechanisms, and all relevant stereochemistry.
1. Cl H
NaNH2 NH3
+ 6. Br
HO H2O OH OH
2. Cl H
NaBr acetone Br
7.
Br
Br
NH3 EtOH N H
Br 3. Cl H KOH + CN 8. NaCN DMSO
4. Cl H
AgNO3 EtOH OEt
+
OEt
9.
Br
AgNO3 EtOH
OEt
+ 5. Cl H CsI MeOH I
I
10.
Br
NaCN DMSO
CN
11. Predict the effect of the changes given below on the rate of the following reaction: NaCN Cl MeOH CN faster faster
a) change the halogen from Cl to I.
b) change solvent from MeOH to DMSO
c) change starting material from 1-chloropropane to 2-chloropropaneslower
12. Rank the following sets in order of increasing SN2 reactivity a) Br CH3Br fastest b) Cl c) fastest Cl fastest Cl slowest Cl I slowest Br slowest Cl
13. Rank the members of the following groups in order of basicity, nucleophilicity, and leaving group ability. Expain your answers. nucleophilicity basicity a) H2O, - OH, CH3CO2 b) Br -, Cl -, F -, I c) - NH2, NH3, - PH2 d) H2O, H2S, NH3 e) NaF, NaOH, NaSMe
-OH
leaving group ability H2O > CH3CH2CO2- > -OH I- > Br- > Cl- >FNH3 > -PH2 > -NH2 H2S > H2O > NH3
-SMe
> CH3CO2 - > H2O
-OH
> CH3CO2 - > H2O
F- > Cl- > Br- > I- NH > - PH > NH 2 2 3
I- > Br- > Cl- >F- PH > - NH > NH 2 2 3
NH3 > H2O > H2S
H2S > NH3 > H2O NaSMe > NaOH > NaF
NaOH > NaSMe > NaF
> -OH > F-