Organic Halide Reaction: Products of Chloroethane and Sodium Hydroxide

In summary, the question is asking what the products are when chloroethane is reacted with sodium hydroxide. There are two possible solutions: ethanol and sodium chloride through a substitution reaction, or ethene, water, and sodium chloride through an elimination reaction. To determine which solution is correct, we need to consider the stability of the carbonium ion intermediate. A primary carbon is involved in this reaction, so it is important to consider if there are any adjacent groups that can stabilize the carbonium ion. Additionally, the type of elimination reaction (E2 or E1) will also affect the stability of the carbonium ion intermediate.
  • #1
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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?
 
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  • #2
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?
 
  • #3
What do you mean by stabilized?
 
  • #4
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.
 
  • #5
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?
 

Related to Organic Halide Reaction: Products of Chloroethane and Sodium Hydroxide

1. What is an organic halide reaction?

An organic halide reaction is a chemical process in which a halogen atom (such as chlorine, fluorine, or bromine) is added or substituted into an organic compound. This can result in the formation of new molecules with different properties and functions.

2. What are some common examples of organic halide reactions?

Some common examples of organic halide reactions include halogenation, nucleophilic substitution, and elimination reactions. Halogenation involves the addition of a halogen atom to an organic compound, while nucleophilic substitution involves the replacement of a halogen atom with a nucleophile. Elimination reactions involve the removal of a halogen atom to form a double bond.

3. Why are organic halide reactions important?

Organic halide reactions are important because they allow for the synthesis of a wide range of organic compounds, which are essential for many industries such as pharmaceuticals, agriculture, and materials science. They also play a crucial role in biological processes, as many enzymes and hormones contain halogen atoms.

4. What are some safety considerations when working with organic halide reactions?

Organic halide reactions can be hazardous due to the toxic and corrosive nature of many halogen compounds. It is important to handle these reactions in a well-ventilated area and wear appropriate protective equipment, such as goggles and gloves. Proper disposal of waste products is also necessary to prevent environmental contamination.

5. How do reaction conditions affect the outcome of an organic halide reaction?

The outcome of an organic halide reaction can be greatly influenced by reaction conditions such as temperature, solvent choice, and the presence of catalysts. These factors can impact the rate of the reaction, the selectivity of products, and the stability of intermediates. It is important to carefully control these conditions to achieve desired outcomes in organic halide reactions.

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