Problems 479- Give the major product expected from the reaction of 2-ethyloxirane with each of the following reagents:
a. 0.1 M HCl c. ethyl magnesium bromide in ether, followed by 0.1 M HCl e.
b. d. 0.1 M NaOH - When ethyl ether is heated with excess HI for several hours, the only organic product obtained is ethyl iodide. Explain why ethyl
alcohol is not obtained as a product. - a. Propose a mechanism for the following reaction:
b. A small amount of a product containing a six-membered ring is also formed. Give the structure of that product.
c. Why is so little six-membered ring product formed?- Identify A through H.
- Greg Nard added an equivalent of 3,4-epoxy-4-methylcyclohexanol to an ether solution of methyl magnesium bromide and then
added dilute hydrochloric acid. He expected that the product would be a diol. He did not get any of the expected product. What
product did he get? - An ion with a positively charged nitrogen atom in a three-membered ring is called an aziridinium ion. The following aziridinium
ion reacts with sodium methoxide to form A and B:
If a small amount of aqueous is added to A, the reddish color of persists, but the color disappears when is added to B.
When the aziridinium ion reacts with methanol, only A is formed. Identify A and B.- Dimerization is a side reaction that occurs during the preparation of a Grignard reagent. Propose a mechanism that accounts for the
formation of the dimer. - Propose a mechanism for each of the following reactions:
a. c.b.OHH+
H 2 OOHH 2 SO 4
∆OHOOH
H+
H 2 OBr MgBra dimer+MgBr 2 Br 2 Br 2N+CC
CH 3
an aziridinium ionH 3 CH 3 C CH 3H 3 C CH 33,4-epoxy-4-methyl-
cyclohexanol1,2-dimethyl-
1,4-cyclohexanediolOOHH 3 COHH 3 COH
CH 3CH 3 Br C CH 3 CH 2 CH 2 OHA
B- D
2. E CH^3 CH^2 CH^2 OCH^2 CH^2 OH- F
- G
- H
CH 2 CH 2 CH 2 BrBr−O CH 2 OCH 3
+CH 3 O−OCH 3 OH>H+CH 3 OH>CH 3 O-BRUI12-437_480r3 27-03-2003 11:51 AM Page 479