Organic Halide Reaction: Products of Chloroethane and Sodium Hydroxide

[temaire]

Homework Statement

When reacting chloroethane with sodium hydroxide, what are the products?

The Attempt at a Solution

I think there are two possible solutions to this problem. One possible solution is ethanol and sodium chloride, through a substitution reaction. Another solution could be ethene, water, and sodium chloride, through an elimination reaction. How do I know which solution the question is looking for?

 

[chemisttree]

Remember that the carbon is primary in this case. Do you know of any elimination reactions on a primary carbon that aren't stabilized by an adjacent group?

 

[temaire]

What do you mean by stabilized?

 

[chemisttree]

If the reaction mechanism calls for a carbonium ion intermediate, something that would donate electron density to that carbonium ion would "stabilize" it. If the carbonium ion intermediate could be delocalized somehow as in an aromatic ring or and some other unsaturated system, that would "stabilize" the carbonium ion.

 

[chemisttree]

The reaction mechanism for the elimination reaction (is it E2 or E1?) involves plucking off an adjacent hydrogen resulting in... what? Is this (primary, secondary or tertiary?) carbonium ion reasonable?