Identifying Preferred Reactivity in Organic Compounds

In summary, when determining which functional group will react in preference in an organic compound, it is important to consider the structure of the molecule rather than just the functional groups present. In the case of an ether and an alcohol, the alcohol will get preference in naming but will not react with excess HI due to loss of aromaticity in resonance. The ether, being less sterically hindered, will react with the acid instead.
  • #1
scott_for_the_game
28
1
In organic if you have more than one functional group.. how do you know which will react in preference?

In the attachment I've got an organic compound which has an ether and alcohol.

In terms of naming the alcohol gets preference.

It reacts with excess HI and the alcohol apparently doesn't react.. chemical changes occur with the ether..
 

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  • #2
my first reaction was that it should react with the alcohol... but if your text or teacher says it doesn't then...

my guess is that instead of looking at "functional groups" per se, try to understand the structure of the molecule. Both oxygens have free electrons but the ether O is farther out from the phenyl ring = less sterically hindered. So then the acid would protonate the ether O instead of the alcohol O. Then again, I could be completely wrong, but that's what makes sense.
 
  • #3
Oh yeah, it won't react with the alcohol because if you protonate the alcohol O, you lose aromaticity in resonance. Since aromaticity is a strong driving force, the reaction with the alcohol O is not favored. Does that make sense?
 

Related to Identifying Preferred Reactivity in Organic Compounds

1. What is the purpose of identifying preferred reactivity in organic compounds?

The purpose of identifying preferred reactivity in organic compounds is to understand how different compounds will behave in chemical reactions. This information is crucial for designing efficient and selective reactions, predicting reaction outcomes, and synthesizing new compounds.

2. How is preferred reactivity determined in organic compounds?

Preferred reactivity in organic compounds is determined by various factors such as functional groups, electronic and steric effects, and reaction conditions. These factors influence the stability and reactivity of the compounds and can be analyzed using techniques such as spectroscopy, computational chemistry, and reaction kinetics.

3. What are the different types of preferred reactivity in organic compounds?

The different types of preferred reactivity in organic compounds include electrophilic, nucleophilic, acid-base, and radical reactivity. These types of reactivity are determined by the electron donating or withdrawing abilities of functional groups and the availability of electron pairs or unpaired electrons.

4. How does preferred reactivity impact the outcome of a chemical reaction?

The preferred reactivity of organic compounds can significantly impact the outcome of a chemical reaction. For example, if a compound has a preferred electrophilic reactivity, it will react readily with nucleophiles, resulting in a different product compared to a compound with preferred nucleophilic reactivity. Understanding preferred reactivity can also help predict the regio- and stereochemistry of a reaction.

5. What are some practical applications of identifying preferred reactivity in organic compounds?

Identifying preferred reactivity in organic compounds has many practical applications, such as drug design, materials synthesis, and natural product synthesis. It can also be used to optimize reaction conditions and develop more environmentally friendly and efficient chemical processes.

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