Final answer:
To prepare the given alcohol using oxymercuration, the four smallest alkenes that can be used are CH3-CH=CH-CH3, CH3-CH2-CH=CH2, CH3-CH=CH-CH3, and CH3-CH=CH-CH3.
Step-by-step explanation:
To prepare the given alcohol using oxymercuration, we need to start with an alkene. Oxymercuration is a reaction in which an alkene reacts with a mercuric acetate compound to form a mercurinium ion intermediate. This intermediate is then hydrolyzed to yield the alcohol.
The given alcohol is CH3O-CH2-CH2-CH3. To draw the structural formulas for all alkenes that could be used to prepare this alcohol, we need to first identify the alkene by removing the -OH group from the alcohol and adding a double bond in its place.
Since the alcohol has 4 carbon atoms, the possible alkenes that can be used to prepare it are:
- CH3-CH=CH-CH3
- CH3-CH2-CH=CH2
- CH3-CH=CH-CH3
- CH3-CH=CH-CH3
These are the four smallest alkenes (also known as butenes) that can be used to prepare the given alcohol by oxymercuration.