Organic Chemistry Leaving groups

In summary, the best leaving group between Cl-, enolate, and NR3 is Cl-. This is because resonance on the enolate will disperse the negative charge, making it a weaker conjugate base. Additionally, HCl, the acid form of Cl-, is a stronger acid than NR3H, the acid form of NR3.
  • #1
destinc
17
0
which is the best leaving group?
Cl- enolate NR3


I couldn't figure out how to draw the enolate here, but it is a basic 3 carbon one.
I believe the answer is Cl because resonance on the enolate will disperse the neg. charge. Am I on the right track or is there a factor I am missing?
 
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  • #2
destinc said:
which is the best leaving group?
Cl- enolate NR3


I couldn't figure out how to draw the enolate here, but it is a basic 3 carbon one.
I believe the answer is Cl because resonance on the enolate will disperse the neg. charge. Am I on the right track or is there a factor I am missing?

strong acid=> weak conjugate base(it is leaving group)=>good leaving group.
I don't know enolate looks like but out of other two Cl is best since it's acid(HCl) is stronger acid than that of NR3(that's NR3H)
 

Related to Organic Chemistry Leaving groups

What is a leaving group in organic chemistry?

A leaving group in organic chemistry is an atom or group of atoms that can dissociate from a molecule, taking with it a pair of electrons. This process is known as leaving group departure and is a crucial step in many organic reactions.

What makes a good leaving group in organic chemistry?

A good leaving group in organic chemistry is one that is stable and able to easily accept the pair of electrons that it takes with it when it dissociates from a molecule. Common examples of good leaving groups include halides (such as chloride, bromide, and iodide) and sulfonates.

Why are certain atoms or groups better leaving groups than others in organic chemistry?

The ability of an atom or group to act as a leaving group in organic chemistry is dependent on its stability and its ability to stabilize the negative charge that is formed when it dissociates from a molecule. Atoms or groups that are more electronegative and have a larger size are typically better leaving groups.

How do leaving groups affect the rate of organic reactions?

The presence of a good leaving group can greatly increase the rate of an organic reaction. This is because a good leaving group makes it easier for the reaction to proceed by stabilizing the negative charge that is formed during the reaction. In contrast, a poor leaving group can slow down or even prevent a reaction from occurring.

Can leaving groups be converted into other functional groups in organic chemistry?

Yes, leaving groups can be converted into other functional groups through various chemical reactions. For example, a leaving group like a halide can be converted into an alcohol through a substitution reaction. This flexibility in functional group conversion is one of the key features of organic chemistry and allows for the synthesis of a wide range of complex molecules.

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