478 CHAPTER 12 Reactions of Alcohols, Ethers, Epoxides, and Sulfur-Containing Compounds- Propose a mechanism for the following reaction:
- When deuterated phenanthrene oxide undergoes an epoxide rearrangement in water, 81% of the deuterium is retained in the product.
a. What percentage of the deuterium will be retained if an NIH shift occurs?
b. What percentage of the deuterium will be retained if an NIH shift does not occur?- When 3-methyl-2-butanol is heated with concentrated HBr, a rearranged product is obtained. When 2-methyl-1-propanol reacts
under the same conditions, a rearranged product is not obtained. Explain. - When the following seven-membered ring alcohol is dehydrated, three alkenes are formed:
Propose a mechanism for their formation.- How could you synthesize isopropyl propyl ether, using isopropyl alcohol as the only carbon-containing reagent?
- Ethylene oxide reacts readily with because of the strain in the three-membered ring. Cyclopropane has approximately the
same amount of strain, but does not react with Explain. - Which of the following ethers would be obtained in greatest yield directly from alcohols?
- Propose a mechanism for each of the following reactions:
a. b.- Indicate how each of the following compounds could be prepared, using the given starting material:
a. d.b. e.c.- Triethylene glycol is one of the products obtained from the reaction of ethylene oxide and hydroxide ion. Propose a mechanism for
its formation.
H 2 CHOCH 2 + −O
HOCH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 OH
triethylene glycolCH 3 CCH 2 CH 2 CH 3CH 3OHCH 3 CHCHCH 2 CH 3CH 3BrCH 3 CH 2 CH CH 2 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3OH CH 2 CH 2 OHCH 3 OH DHBr
∆ Br CH^2 CH^2 CH^2 CH^2 CH^2 Br H^2 O
O+H+
HOCH 2 CH 2 CH 2 CH 2 OH H 2 O
O+CH 3 OCH 2 CH 2 CH 3 CH 3 CH 2 OCH 2 CH 2 CH 3 CH 3 CH 2 OCH 2 CH 3 CH 3 OCCH 3CH 3CH 3HO-.HO-∆H 2 SO 4
+ +CH 3CH 3CH 3
CH 2
CH 3CH 3 CH 3 CH 3
H 3 CCH 3 CH 3
H 3 C OHHDOCH 3 CHCH CH 2 CH 3 O−Cl+ CH
3 OHCH 3 CH CHCH 2 OCH 3 + Cl−O OBRUI12-437_480r3 27-03-2003 11:51 AM Page 478