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Why doesn't HBr show allylic substitution in presence of Peroxide?

HBr reacts with alkenes such as propene in the presence of Peroxide as per the Anti-Markovnikov rule. This is an addition reaction, forming 1-bromopropane as the major product. This happens due to the ...
Maddy's user avatar
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8 votes
2 answers
636 views

Stereochemistry of nitrosyl chloride addition to an alkene

My book states addition of $\ce{NOCl}$ to propylene results in 2‐chloro‐1‐nitrosopropane: Would it follow syn or anti addition? According to Mallya and Nagendrappa [1], the reaction would follow syn ...
Hydro_7's user avatar
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3 votes
0 answers
1k views

Cram's rule vs Felkin Anh's model

I am getting two different products based on the Cram and Felkin-Anh models as shown in the diagram. Any explanation?
adianadiadi's user avatar
-1 votes
1 answer
257 views

Electrophilic addition to benzene [closed]

A question deals with electrophilic addition to the following compound; Apparently, the benzylic carbon gets a positive charge during electromerism, invoking resonance stabilization. Benzene is an ...
harry's user avatar
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1 vote
1 answer
184 views

Electrophilic attack of X+ on double bond

Is it the double bond attacking the $\ce{X+}$ ion or the other way around? Also, does it form a cyclic transition state if it isn't bromine or chlorine? Eg. cyclohexene $+ \,\ce{Cl+ ->}$ cyclic ...
ganuwoahh's user avatar
4 votes
1 answer
603 views

Can enamines be formed from α,β-unsaturated ketones?

This question was a result of discussion form here: α,β-unsaturated carbonyl compounds and alkyl addition The reaction below (condensation of cyclohexenone with a secondary amine) does not yield any ...
Outlander's user avatar
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-2 votes
1 answer
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difference between elimination reactions and oxidation reactions [closed]

I know that oxidation reactions involve the loss of hydrogen. But is the mechanism the same
Y-MinG's user avatar
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6 votes
1 answer
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In the addition of HBr to isoprene why does the less stable carbocation form? [duplicate]

According to me, the answer is B as the tertiary allylic carbocation should be more stable. But the answer given is D and in the given solution, the tertiary allylic carbocation rearranges to primary ...
Polario's user avatar
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1 answer
1k views

Carbocation Stability: Tertiary versus Secondary Benzyl for Hydrobromic Acid Addition

I haven't been able to find anything concrete or consistent on this topic. For the following reactions, which product would be favored, assuming that they both have to go through a carbocation ...
Bob's user avatar
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0 votes
0 answers
291 views

Steric hindrance during Hydroboration

In response to this diagram (Organic Chemistry By David Klein 3rd Edition Page 364): The textbook stated A comparison of the transition states for hydroboration via Markovnikov addition or anti-...
George Tian's user avatar
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8 votes
2 answers
10k views

Why does NOCl dissociate as +NO and Cl-?

$\ce{N}$ is more electronegative than $\ce{Cl}$ (albeit by a very small difference) but it should ideally dissociate as $\ce{Cl+}$ and $\ce{^-NO}$ (similar to the dissociation of $\ce{Cl}$ in $\ce{...
Neha Malcom's user avatar
2 votes
0 answers
44 views

Addition Reaction

Why does the following addition reaction use radicals rather than using the normal transfer of hydrogen (seen in last picture)? I would think that because the reaction has no light to indicate ...
Sarah Smith's user avatar
8 votes
1 answer
2k views

Isocyanides undergo addition reactions, but cyanides do not. Why?

My book mentions addition reactions of isocyanides with halogens, ozone, sulphur, etc. but it doesn't mention any such reaction for cyanides. Instead, it bluntly states: "Cyanides do not undergo ...
Gaurang Tandon's user avatar
9 votes
2 answers
1k views

What is the driving force for imine formation?

I know this that when a primary amine is reacted with a carbonyl compound, an imine is formed: I'm wondering why the position of this equilibrium lies to the product side / right-hand side. Why is ...
Selena's user avatar
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1 vote
1 answer
460 views

Mechanism for cyclic enamine formation after N-Boc deprotection

In this reaction taken from Snyder's total syntheses of Coccinellid alkaloids,1 how does the Boc deprotection lead to ring closure? I understand that the $\ce{PBr3}$ step simply converts the alcohol ...
Clara's user avatar
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5 votes
1 answer
9k views

Cram's rule for nucleophilic addition to carbonyl groups

I recently heard about Cram's rule for predicting the stereoselectivity in nucleophilic additions to carbonyl groups. Can anybody explain what this is and whether it is an accurate rule?
maulik M's user avatar
5 votes
3 answers
1k views

Effect of protecting group on diastereoselectivity of LiAlH4 reduction of α-hydroxyketones

In the reactions above, taken from Tetrahedron Lett. 1982, 23 (23), 2355–2358, the choice of protecting group on the α-hydroxyl group has a large influence on the diastereoselectivity of reduction. ...
user avatar
5 votes
1 answer
8k views

What is the major product formed on addition of Hydrogen Iodide to Pent-2-ene?

Orginal question: (1) One of the carbocations formed (CC on the right) is only slightly more stable than the other (both are 2°). (2) Iodine ion ($\ce{I-}$) is a slightly bigger ion and it faces more ...
Sujith Sizon's user avatar
9 votes
1 answer
8k views

Order of reactivity of carbonyl compounds to Nucleophilic addition reaction

One of the questions in my textbook was to arrange the following in order of their reactivity for nucleophilic addition reaction. $\ce{(p-NO2Ph)_2CO}$ $\ce{(CH3)_2CO}$ $\ce{(p-NO2Ph)COH}$ $\...
stochastic13's user avatar
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