ETHYL PROPYL ETHER

CH3CH=CH2 + CH3CH2CH2OCH2CH3 Propene (9%) Ethyl propyl ether (91%)... 

Ethyl propyl ether 109 C5Hi20 Sulfur trioxide 2.30 S02... 

Bromine B 43 Ethyl propyl ether B 72 Propyl acetate A... 

Consider the reaction of ethyl propyl ether with HI. Write the two different possible product combinations. Compare e energies of the two products 1-propanol and ethyl iodide-, ethanol and 1-propyl iodide). Which is the lower-energy combination Is the energy difference significant (>.002 au or 1 kcal/mol) Based on thermochemistry alone, is this reaction Likely to be selective Explain. 

Selective ether cleavage comes about during the substitution step, which obeys an Sn2 mechanism. Therefore, selective cleavage requires selective attack by Y on one of the electrophilic carbons in the protonated ether. Determine if selective attack is likely by examining the shape of the lowest-unoccupied molecular orbital (LUMO) in protonated ethyl propyl ether. Is this orbital larger near one carbon than the other If so, what product combination will result What other atom(s) contribute to the LUMO What would happen if 1 attacked this atom(s) ... 

Repeat this analysis for the reaction of phenyl methyl ether with HI leading to phenol and methyl iodide or methanol and phenyl iodide and involving protonated phenyl methyl ether as an intermediate. (Note In this case, the appropriate empty molecular orbital is LUMO+2 the LUMO is concentrated primarily on the CO bond.) Which reaction, with ethyl propyl ether or phenyl methyl ether, appears to be more likely to give selective ether cleavage ... 

LUMO of protonated ethyl propyl ether reveals likely site of nucleophilic attack. 

IB-2 A mixture of diethyl ether, dipropyl ether, and ethyl propyl ether is formed in a 1 1 2 ratio. 

Write the formula of (a) ethyl methyl ether, (b) ethyl propyl ether (c) dimethyl ether... 

METHYL-1-BUTANOL 2-METHYL-2-BUTANOL 2 2-DIMETHYL-l-PROPANOL ETHYL PROPYL ETHER METHYL-T-BUTYL ETHER BUTYLMETHYL ETHER... 

Ethyl benzene Ethyl bromide 2-Ethyl butyl acrylate Ethyl chloride Ethyl ether Ethyl formate 2-Ethyl hexyl acrylate Ethyl iodide Ethyl propionate Ethyl propyl ether Ethyl sulfide Ethylene bromide Ethylene chloride Ethylene glycol Ethylidebe chloride Fluorobenzene Formic acid Freon-11 Freon-12 Freon-21 Freon-22 Freon-113 Glycerol, 100%... 

Step 2 The full name is ethyl propyl ether. 

METHYL sec-BUTYL ETHER METHYL tert-BUTYL ETHER METHYL ISOBUTYL ETHER ETHYL PROPYL ETHER ETHYLENE GLYCOL MONOPROPYL NEOPENTYL GLYCOL... 

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