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Questions tagged [nucleophilic-substitution]

For questions having their focus on SN1, SN2, SNi, SN1', SN2', or SN2th (nucleophilic acyl substitution).

From Wikipedia:

In organic and inorganic chemistry, nucleophilic substitution is a fundamental class of reactions in which an electron rich nucleophile selectively bonds with or attacks the positive or partially positive charge of an atom or a group of atoms to replace a leaving group; the positive or partially positive atom is referred to as an electrophile. The whole molecular entity of which the electrophile and the leaving group are part is usually called the substrate.

The most general form of such reactions is:

$$\ce{Nuc: + R-LG -> R-Nuc + LG:}$$

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What are the partial charges in an SN2 transition state?

What are the partial charges of on the atoms in a SN2 reaction? The nucleophile is normally negatively charged and has a lone pair of electrons. This would make you think the transition state would have a negative charge on the nucleophile. The…
user9995331
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Order of reactivity of nucleophilic addition at carbonyl group with Grignard reagent

I thought the order would be $1 > 3 > 2$ as 1 is aldehyde and 2, 3 are ketones. As generally aldehydes are more reactive, I placed it first. I chose 3 over 2 as two alkyl groups would make cleaving of $\ce{C=O}$ difficult in 2. But the answer is…
Hydroquinone
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How to compare SN2 rate of cyclopropane with bridged cyclic compound?

How to compare the SN2 rate of iodocyclopropane and 1-iodobicyclo[2.2.1]heptane? Backside attack is must, but as the cyclopropane ring is planar it's quite impossible for back side attack. Then the bridge compound is non planar, we know in bridge…
Apurba Adhikary
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How do nucleophiles change Sn1 energy profiles?

Suppose two different nucleophiles react with a single substrate via SN1. Would the energy of activation for the second transition state (nucleophile reacts with carbocation) be less for the better nucleophile? Would the products be of equal energy…
Reese
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Why is this reaction not feasible?

The reaction is:$$NH_3+CH_3OCH_3 \rightarrow CH_3NH_2+CH_3OH$$ The mechanism here would be $S_N2$ and since $NH_3$ is a stronger base so it should be a better nucleophile. Why then is this reaction not feasible? Any help would be appreciated.
Sameer Thakur
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Which of the following has maximum nucleophilicity?

Question The answer should be (D) as the inductive effect of 3 methyl groups increases negative charge on oxygen and thus makes it a good nucleophile.But the answer is (A).
Isha Roy
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What is the energy of activation of uncatalyzed ATP hydrolysis reaction?

If we ignore all the biological significans for a while, ATP hydrolysis, the reaction: ATP + H2O -> ADP + Pi is still a chemical reaction that must go through transition state to yield product. This is no doubt a nucleophillic substitution reaction…
Anik Samiur Rahman
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Nucleophilic Substitution

when I add $\ce{RCl + H2O -> ROH + HCl}$ but it's also true in reverse $\ce{ROH + HCl -> RCl +H2O}$ however this is not in case of $\ce{FeSO4 +Zn -> Zn + FeSO4}$ $\ce{ZnSO4 + Fe -> no rxn}$ How can a reaction be true both ways ?
Bhavay
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chlorination of aromatic compounds

I was reading some notes on Electrophilic Substitution and I came across the topic chlorination of Toluene. I'm wondering why we cannot substitute chlorine in the meta position of toluene?
Lakshmi Narayanan
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