11 - OEt a) H 2 O, - OH, CH 3 CO 2-OEt b) Br -, Cl -, F -,...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
Cl H Cl H Cl H Cl H Cl H Br Br Br Br Br Chem 212 Alkyl halide problems 3 NaNH 2 NH 3 NaBr acetone KOH Cl AgNO 3 EtOH CsI MeOH CN H 2 O NH 3 EtOH NaCN DMSO Br AgNO 3 EtOH NaCN DMSO 1. Br 2. 3. Cl 4. I 5. Cl 6. 7. Cl 8. Cl 9. Cl 10. 11. Predict the effect of the changes given below on the rate of the following reaction: NaCN MeOH a) change the halogen from Cl to I. b) change solvent from MeOH to DMSO c) change starting material from 1-chloropropane to 2-chloropropane 12. Rank the following sets in order of increasing S N 2 reactivity a) CH 3 Br Provide the products for the following reactions, show the mechanisms, and all relevant stereochemistry. b) Br c) 13. Rank the members of the following groups in order of basicity, nucleophilicity, and leaving group ability. Expain your answers.
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: OEt a) H 2 O, - OH, CH 3 CO 2-OEt b) Br -, Cl -, F -, I -c) - NH 2 , NH 3 , - PH 2 d) H 2 O, H 2 S, NH 3 e) NaF, NaOH, NaSMe + OEt + CN + CN N H faster faster slower fastest slowest slowest slowest fastest fastest Br OH basicity-OH > CH 3 CO 2-> H 2 O F-> Cl-> Br-> I-- NH 2 > - PH 2 > NH 3 NH 3 > H 2 O > H 2 S NaOH > NaSMe > NaF nucleophilicity I-> Br-> Cl->F-NaSMe > NaOH > NaF H 2 S > NH 3 > H 2 O-OH > CH 3 CO 2-> H 2 O- PH 2 > - NH 2 > NH 3 leaving group ability I-> Br-> Cl->F--SMe > -OH > F-H 2 O > CH 3 CH 2 CO 2-> -OH NH 3 > -PH 2 > -NH 2 H 2 S > H 2 O > NH 3 I I + HO OH...
View Full Document

Ask a homework question - tutors are online