Most likely carbons for nucleophilic attack on a molecule

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In summary, the conversation is discussing the likelihood of nucleophilic attack on a molecule with a ring structure. The answer key suggests that only molecules a and c are likely candidates, but the speaker argues that molecule b could also be nucleophilic due to its alkene carbon furthest from the bromine. However, the presence of the ring structure and the steric hindrance it creates may make this less likely. The conversation concludes with the speaker seeking input from others on the matter.
  • #1
blueberryfive
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Homework Statement

I've attached a picture of the molecule. The question: at which molecules (s) would it be likely that there would be a nucleophilic attack?

Homework Equations


The Attempt at a Solution



The answer key says a and c, only. However, I think that b is nucleophilic because the nucleophile can attack the alkene carbon furthest from the bromine, which would shift the alkene up, knocking off the bromine.
 

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  • #2
blueberryfive said:

Homework Statement




I've attached a picture of the molecule. The question: at which molecules (s) would it be likely that there would be a nucleophilic attack?


Homework Equations





The Attempt at a Solution



The answer key says a and c, only. However, I think that b is nucleophilic because the nucleophile can attack the alkene carbon furthest from the bromine, which would shift the alkene up, knocking off the bromine.

Nucleophilic attack can take place if b is the carbon on the right of the double bond but I don't know if the ring structure makes a difference. Let's see what others have to say on this. :)
 
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  • #3
B is an SP2-hybridized bridgehead carbon. A pretty poor nucleophile. The attacking species would need to approach from one of the faces axially to the ring system which is fairly sterically restrictive. Were it simply an open allylic system, your analysis would be correct.
 
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1. What is a nucleophilic attack?

A nucleophilic attack is a type of chemical reaction where a nucleophile, which is an electron-rich species, attacks and forms a bond with an electron-deficient atom or group in a molecule.

2. What are the most likely carbons for nucleophilic attack?

The most likely carbons for nucleophilic attack are those that have a partial positive charge, such as a carbonyl carbon, or those that are attached to electron-withdrawing groups, such as a halogen or a nitro group.

3. How does the carbon's electronic environment affect its susceptibility to nucleophilic attack?

The carbon's electronic environment influences its susceptibility to nucleophilic attack by determining the availability of its electrons for bond formation. A carbon with a partial positive charge or attached to electron-withdrawing groups will have a higher electron density, making it more susceptible to nucleophilic attack.

4. Can steric hindrance affect the likelihood of nucleophilic attack on a carbon?

Yes, steric hindrance can affect the likelihood of nucleophilic attack on a carbon. If the carbon is surrounded by bulky groups, it may be more difficult for a nucleophile to access and attack the carbon, decreasing the likelihood of a reaction taking place.

5. Are there any exceptions to the rule of most likely carbons for nucleophilic attack?

Yes, there are exceptions to this rule. For example, a carbon-carbon double bond can undergo nucleophilic attack at either carbon due to the high electron density of the pi bond. Additionally, some functional groups, such as amines, can also act as nucleophiles and undergo attack on carbons that are not typically susceptible to nucleophilic attack.

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