Questions tagged [nucleophilic-substitution]
For questions having their focus on SN1, SN2, SNi, SN1', SN2', or SN2th (nucleophilic acyl substitution).
186
questions
0
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1answer
49 views
Why does the reaction between 2‐methylbut‐3‐en‐2‐ol and hydrogen bromide show allylic shift?
In the following reaction
shouldn't the minor product be the major one as the carbocation formed before attachment of bromine is 3°? Also, can someone tell me why the product includes only ...
0
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0answers
33 views
Confused about inversions in $S_N2$ Reaction
I just learned that in $S_N2$ reaction there is an inversion of configuration. I thought that it is a change of $R$ to $S$ and vice-versa. But that is wrong as mentioned in this answer.
While I was ...
3
votes
0answers
28 views
Favourability of leaving groups in nucleophilic aromatic substitution
It is known that the order of leaving group favourability of the halide ions changes when we go from nucleophilic substitution, in the form of $
\ce {S_N1}$ and $\ce {S_N2}$ reactions, to nucleophilic ...
1
vote
2answers
51 views
Acidic cleavage of ether with a 2° alkyl group
I know that an ether with a 3° alkyl group and a 1° alkyl group is cleaved by $\mathrm{S_N1}$ mechanism to give a tertiary alkyl halide and a 1° alcohol.
And an ether with a two 1° alkyl groups is ...
0
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0answers
14 views
Explanation of SN2 Mechanism using MOT
SN2 is usually explained by MOT, where we state that the incoming nucleophile starts donating the electron density into the σ∗ orbital and the carbon-leaving group bond weakens and finally breaks and ...
0
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0answers
35 views
Why can't carboxylic acid + NaH + tert-butyl bromide react to create an ester?
So, the picture I showed above asks for which reagents can form the ester product. I was wondering why D can't form it? I was thinking that first, the $\ce{NaH}$ would react with the carboxylic acid ...
0
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0answers
13 views
Why does the hydride ion in LAH act as a nucleophile rather than a base in the reduction of carbonyl compounds? [duplicate]
Why does the $\ce{H-}$ ion in $\ce{LiAlH4}$ act as a nucleophile rather than a base in the reduction of carbonyl compounds ??
Because $\ce{H-}$ being a small ion would act as a better base than a ...
2
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0answers
37 views
Why doesn't Grignard reagent attack alkyl halides [duplicate]
When we add magnesium to
alkyl halide, Grignard reagent is formed. $$\ce{R-X + Mg -> RMgX } $$ It is highly nucleophilic in nature. Now at this time the electrophilic alkyl halide is also present ...
0
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1answer
51 views
Adding cyanide vs nitrite for nucleophilic substitution and why does it change when we use silver salts for it
On adding $\ce{NaCN}$ to $\ce{RX}$, we get
$$\ce{NaCN + RX -> RCN + NaX}$$
And not $\ce{RNC}$. Clayden gives the explanation as follows:
Although linear cyanide (which is isoelectronic with $\...
0
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1answer
47 views
What is the major product of the reaction between 4-chlorobut-1-ene?
When acetic acid looses hydrogen, an acetate ion is formed which attacks 4-chlorobut-1-ene, forming methyl butenoate. How does the cyclic structure form?
Does the lone pair of oxygen attack the butene ...
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0answers
36 views
Formation of isocyanide on reaction with silver cyanide whereas sodium cyanide forms a regular cyanide
Organic halide react with silver cyanide and an isocyanide is formed, whereas on reaction of sodium cyanide, normal cyanide is found.
What is the reason behind the difference in the products??
In a ...
2
votes
1answer
43 views
Rearrangement considerations in feasibility of SN1 in given reactants
I have been asked to compare the feasibility of Unimolecular Nucleophilic Substitution ($\mathrm{S_N1}$) in the following question.
I have received instruction that the reaction will be feasible only ...
0
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0answers
23 views
Iodide via SN1 in anhydrous medium
In anhydrous medium fluoride ion is the strongest nucleophile whereas iodide is the weakest.
I was wondering if in anhydrous conditions, SN1 reaction with an iodide could take place.
I have been ...
0
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0answers
20 views
Rate of reaction of halogens in a substitution reaction
When a substitution reaction takes place in a substrate having halogen,
Why is it that iodine reacts the fastest and fluoride is the slowest ?
For sure the iodine has a weaker bond but it is also ...
-1
votes
1answer
40 views
Addition of aqueous KOH to 3-bromobut-1-ene
On addition of aq $\ce{KOH}$ to 3-bromobut-1-ene, substitution reaction should take place via $S_N1$ mechanism but in this an allylic carbocation forms which could rearrange.
In that case which ...
0
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0answers
31 views
Addition v/s elimination with double bond and OH together
If a compound has both an hydroxyl group and a double bond and we add $\ce{HBr}$ to it,
(a) substitution reaction to the hydroxyl group can take place, or
(b) an addition reaction of a ...
-1
votes
1answer
37 views
Methyl iodide in water
Iodide being a good leaving group and water being quite a weak $\ce{Nu-}$, does $\ce{CH3I}$ undergo $\mathrm{S_N1}$ reaction? I was taught that whenever a protic solvent which can ionize the halide ...
1
vote
0answers
45 views
Reactivity of Grignard reagent
I had the following question at an exam:
What is the fastest reacting compound towards nucleophilic addition with Grignard reagent?
(a) Acyl chloride
(b) Aldehyde
(c) Ester
It is ...
0
votes
2answers
97 views
Williamson Ether and Carboxylic Acids
What would happen if you tried a Williamson Ether Synthesis on something that has both an alcohol and a carboxylic acid? Would both -OH groups be functionalized, where the alcohol would become an ...
0
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0answers
29 views
How to rationalise the difference in reactivity between alcoholic and aqueous KOH with alkyl bromides? [duplicate]
Why is it that when we use alcoholic $\ce{KOH}$ with say $\ce{R-Br}$, E2 elimination occurs, whereas with aqueous $\ce{KOH}$, SN reaction takes place, as both have the same nucleophile, ie $\ce{OH^-}$?...
-1
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1answer
58 views
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 ...
2
votes
1answer
59 views
Why aren't there 2 products formed?
The question is asking for the major organic product. This seems like an $S_N1$ reaction to me as there is a weak base in $\ce{CH3OH}$ and heat. If it is, shouldn't there be 2 products. One with the $\...
0
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0answers
56 views
Why does SN1 not occur as a minor product when a strong nucleophile/strong base attacks a tertiary substrate?
The following is part of a table that appears in my Organic Chem Text (Klein)
Nucleophile Only (e.g. Strong Nucleophile/ Weak base)
$1^\circ - \text{ SN2}\\
2^\circ - \text{ SN1 + SN2}\\ 3^\circ - \...
2
votes
1answer
17 views
When will acid-base reactions occur before substitution reaction
For example, given the reaction below:
The substrate is secondary, the solvent is aprotic and it is to react with a strong bulky base. From this, I assumed that the reaction would be $\ce{E2}$. ...
1
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0answers
48 views
Why is the nucleophilic substitution of OH- with 1-bromopentane slower than with 2-bromo-2-methylbutane?
Which statement about the reaction of a hydroxide ion with the organic reagent is correct?
A. 1-bromopentane predominantly follows an $\mathrm{S_N1}$ mechanism.
B. 2-bromo-2-methylbutane ...
0
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0answers
41 views
Does a non-chiral substrate (2-bromo-2-methylpropane) also form two products via an SN1 mechanism?
If I have an alkyl halide, in which its tertiary carbon is non-chiral (for example 2-bromobutane), which reacts via an SN1 mechanism does it also produce 2 products?
I am asking because I know that ...
4
votes
1answer
71 views
Why do we use LiCl as a source of chloride ions as nucleophile but not other alkali metal chlorides? [closed]
$\ce{LiCl}$ has higher covalent character than other alkali-metal chlorides, so in polar solutions like ethanol, its ioniztion will be less, and so less chloride ions will be available for ...
4
votes
1answer
296 views
Why do polar aprotic solvents favour SN2 over E2?
I was reading about Substitution and Elimination Reactions and I came across the following on MasterOrganicChemistry:
Polar protic solvents tend to favor elimination (E2) over substitution (SN2). ...
4
votes
1answer
75 views
Stereochemical outcomes in opening of vinyl epoxides
Explain the outcomes of the following reactions. In each case the major product is shown.
Firstly, I don't understand why the chloride always attacks on the right hand side of the epoxide. Also,...
3
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0answers
34 views
Halogen bonding in organic reactions
Recently, a group of researchers from the Nanyang Technological University in Singapore have investigated the novel $\ce {S_N2X}$ mechanism which involves a "frontside attack" on the substrate, rather ...
0
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1answer
23 views
Do the mechanism (SN1 or SN2 ) which reaction follow depends more upon intermediate stability than on substrate and nucleophilic?
For eg : would the reaction of 3-methylbut-2-en-1-ol with HBr follow SN1 mechanism due to stability of your intermediate carbocation stability or SN2 due to the compound being primary alcohol and ...
0
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0answers
56 views
Why doesn't solvent form the major product in SN1 reactions?
If in a reaction SN1 pathway is followed then after the formation of carbocation the reagent or the solvent molecule can attack to form the product. As the number of solvent molecules are ...
2
votes
2answers
133 views
Why is it aqueous and ethanolic conditions for nucleophillc substitution of cyanide ion with benzyl chloride?
I was doing an exam question where benzyl chloride was undergoing a nucleophilic substitution with cyanide ion to form benzyl cyanide.
Please can someone enlighten me as I have never seen both ...
0
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0answers
248 views
Reaction of ketones with sodium amide
Find the product of the reaction of dimethyl ketone i.e. $\ce{CH3C(O)CH3}$ with $\ce{NaNH2}.$
Should I do nucleophilic addition and form the product in the picture?
1
vote
1answer
69 views
Why doesn't open-chain glucose react with water readily in aqueous solution?
Though the exact number given varies from 0.02% to 3%, it's well agreed that glucose spends a very small percentage of its time in aqueous solution as a linear aldehyde. Glucose's overwhelming ...
10
votes
1answer
167 views
Is isobutyl chloride or ethyl chloride more reactive in an SN1 reaction?
Compare the rate of $\mathrm{S_N1}$ reaction in the following compounds:
We see that both compounds form primary carbocations. However, there is more hyperconjugation in the second compound as ...
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0answers
38 views
Which of these chlorides is more reactive? [duplicate]
We do learn that for $\mathrm{S_N1}$ reaction the rates are tertiary > secondary > primary > methyl. The reasons mentioned are usually inductive and hyper-conjugative effect.
But which of the ...
4
votes
1answer
53 views
Can the nitrogen of an amide displace a primary chloride in a S_N_2 reaction in the presence of a strong base?
I was looking at the following reaction and am confused.
It appears that $\ce{N}$ is attacking the $\ce{C-Cl}$ and $\ce{Cl}$ is leaving in a $\mathrm{S_N2}$ reaction. I know that $\ce{Cl}$ is a good ...
1
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0answers
35 views
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 ...
0
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0answers
42 views
In nucleophilic acyl substitution, why will the Nu never displace the leaving group (e.g., Cl) directly by an SN2 mechanism?
In my class notes, it says: "The Nu will NEVER displace the leaving group directly in an SN2 reaction."
We have previously been taught that SN2 reaction only occur at tetrahedral carbons, so I can ...
0
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0answers
29 views
Distinguishing between a nucleophilic substitution and an electrophilic substitution
Why don't we consider all nucleophilic substitution reactions as electrophilic reactions and vice versa?
For example, look at this reaction I found in my textbook. (See picture)
This is an ...
1
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1answer
95 views
Confusion about the Sn1 and Sn2 Mechanism
My book says, and I understand, that the Sn1 mechanism is much faster for tertiary alkyl halides than primary. And the opposite for Sn2. This all makes sense. What I don't get is the conclusion it ...
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0answers
138 views
Why don't acyl chlorides give positive test with 2,4-DNPH?
In this post, Ron discusses the reasons why carboxylic acid derivatives such as amides, acids and esters do not give a positive result with 2,4-dinitrophenylhydrazine. He mentions that it is largely ...
1
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0answers
82 views
How many moles of methyl iodide will be consumed by one mole of crixivan?
My take on this question : a total of 5 moles of $\ce{CH3I}$ should be consumed.
The oxygen atoms in the $\ce{2 OH}$ groups each have a lone pair of electrons. They should displace $\ce{I-}$ from ...
0
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0answers
19 views
Oxirane and ring opening
I have a problem given as :- I thought of a sn1 type mechanism in acidic medium and a sn2 pathway in basic medium . Am I correct or not . Please also check the mechanism according to which I formed ...
0
votes
1answer
86 views
Bromination of but-3-en-1-ol in basic medium and Baldwin's rules
After formation of the bromocarbocation the alkoxide anion attacks the bromocarbocation which leads to ring formation and can proceed through two pathways
5 endo tet cyclization is disfavored but 4 ...
0
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0answers
94 views
Nucleophilic addition - Propanal vs Benzaldehyde
According to my school textbook, carbon atom of the carbonyl group benzaldehyde is less electrophilic than that of propanal because polarity of the carbonyl group is reduced in benzaldehyde due to ...
-1
votes
1answer
51 views
SN2 reactions with primary alcohols [closed]
A problem I was recently working on poses the following scenario:
A student realizes that protonation of an alcohol makes the -OH into a better leaving group. Therefore, he suggested the following ...
1
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1answer
309 views
Order of reactivity of hydrogen halides
Solomon and Fryhle $11^{th}$ edition says :
Order of reactivity of HX in the acid catalyzed conversion of alcohols to alkyl halides follows the order : HI>HBr>HCl
We can account for this by saying ...
1
vote
1answer
53 views
Reaction of cyclobutylmethanol with HX
I am interested in the reaction of cyclobutylmethanol with HX where these are the only reagents.
My question is whether the reaction proceeds via SN1 or SN2. My reference text insists that primary ...
