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Questions tagged [c-c-addition]

For questions about addition to C–C π bonds (i.e. C=C or C≡C).

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Markovnikov Rule of Alkenes

$$\ce{CH3CH(CH3)CHCHCH2CH3 + HBr ->}$$ According to Markovnikov Rule, "the rich get richer". But, as we can see the 2 carbons have the same amount of $\ce{H}$. So, what's probably the answer?
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Electrophilic addition of IBr to alkene

I would assume options A and B are possible products due to the $\ce{I+}$ electrophile attacking the alkene, and hence are ruled out. However, I am torn between options C and D. Both products are ...
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1answer
88 views

Regioselectivity of bromination of alkenes

Recently, in my chemistry lesson, we were discussing the mechanism of the bromination of alkenes. The teacher brought up the involvement of the cyclic bromonium intermediate. She also mentioned that ...
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Mechanism of photochemical hydroamination with LDA

I've recently come across a couple examples of intramolecular alkene hydroamination accomplished by treatment with LDA followed by visible light irradiation (tungsten light bulb):[1,2] I'd assume ...
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Preferential methylation of sp2 carbons

I'm attempting to methylate a carbon in an isoxazole ring. However, the molecule also has, depending on what I've reacted it with, either an exposed amine or exposed hydroxyl groups. Obviously ...
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1answer
38 views

How far-reaching is the effect of conjugation?

Due to conjugation, it is possible for 1,4-addition, or conjugate addition, to occur. I was thinking, since conjugation and resonance effects do no diminish with distance, unlike inductive effects, ...
3
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1answer
46 views

Conjugate addition vs Electrophilic addition

I was just doing an organic chemistry problem from an online source recently, on the topic of conjugate additions (or 1,4-additions). Below is an image illustrating the problem. I chose the upper ...
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109 views

What is the major product formed when 2-bromopropene reacts with HBr?

On which carbon would the Br atom added to? Does this reaction follow Markovnikov's rule? Attempt: I haven't learnt the mechanism of Markovnikov's rule at my school level, my textbook just said that ...
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1answer
141 views

On the addition of HCl to a conjugated diene [closed]

Is this allylic chloride formed by an ionic or radical mechanism? Is it the more stable isomer?
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90 views

Sigma bond behaving as stronger nucleophile despite presence of pi bond?

In my book, the following reaction is given The solution states that the sigma bond between hydrogen and carbon (3 degree) in isobutane attacks $\ce{H+}$ from $\ce{HF}$ to generate tert-butyl ...
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1answer
290 views

Why do more substituted alkenes undergo epoxidation, but the less substituted alkenes undergo hydrogenation?

We know that, in case of a choice, catalytic hydrogenation will hydrogenate the less substituted alkene, because the less substituted alkene is less stable. But, we also know that, in case of a ...
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1answer
390 views

Why doesn't the bromide anion attack during electrophilic addition of bromine in methanol solvent?

It is known that addition of bromine (in methanol) to ethene will yield 1-bromo-2-methoxyethane. The reaction proceeds with the formation of a bromonium intermediate in the first step. In the second ...
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1answer
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How to decide what pathway a reaction will follow, elimination, addition to a carbonyl or nucleophilic substitution?

There is a substrate such as this, and it is treated with alcoholic KOH. I know that a hydrogen in $\alpha$-position to the carbonyl group will be abstracted, leaving a carbanion. My query lies in ...
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In halogenation of ethene using bromine for example, why does the lone pair of bromine attack the C atom?

In the presence of the electron rich (pi bond) of ethene, the bromine molecule becomes a temporary induced dipole, one end being electron deficient and acting as the electrophile. (The pi bond in) ...
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1answer
209 views

In the presence of an electron-rich species, why is Br2 the stronger electrophile than water? [closed]

In the electrophilic addition of aqueous bromine to ethene, the first slow step involves the electron rich (pi bond) of ethene attacking the bromine molecule to form a carbocation and Br-: And, then ...
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2answers
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Bromonium ion or Mesomeric effect ( intermediate during addition to alkenes)

It's mentioned in Peter Sykes , A Guidebook To Mechanism In Organic Chemistry , 6th edition, 13th impression by Pearson, Pg. No. 185 , that on addition of $\ce{HBr}$ to bromoethene the only product ...
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1answer
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Electrophilic addition to alkenes

Consider the addition of HBr (in absence of any radical initiators or environment that promotes radical mechanistic pathway), to 3-bromocyclopentene. The first step is the attack of $\ce{H^+}$ On the ...
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1answer
225 views

Why must polymers have a repeating unit?

In organic chemistry, we learned that small molecules can form a polymer via a process called polymerization. For example, $\ce{CH2=CH-Br}$ molecules can form the polymer \begin{align} \ce{nCH2=CH-Br-...
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481 views

Regioselectivity in addition of hydrogen iodide to vinyl chloride

I encountered a question which was stated as: The reaction of vinyl chloride with hydrogen iodide to give 1-chloro-1-iodoethane is an example of anti-Markovnikov addition. Is this true or false? ...
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1answer
527 views

Why does boron add to the less substituted carbon in the hydroboration of an alkene?

In the hydroboration of a typical alkene, the boron fragment ends up attached to the less substituted carbon: What are the electronic or steric factors that lead to this regioselectivity?
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Reactivity order in hydrogenation reaction of but-2-yne and butene isomers

Question 1: The reactivity order towards hydrogenation of the following compounds is: but-2-yne ($\ce{CH3-C\bond{3}C-CH3}$) cis-but-2-ene ($\ce{CH3-CH=CH-CH3}$) trans-but-2-ene ($\ce{...
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Product of the addition of 1 eq. bromine to 1-methylcyclohexa-1,4-diene

When we add one equivalent of $\ce{Br2}$ then which double bond will get brominated? The double bond in the molecule with methyl group will be more stable as it will have more hyper conjugating ...
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3answers
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Why does bromine add to a double bond instead of a triple bond if both are present?

According to my textbook, the addition of bromine to pent-1-en-4-yne at low temperature yields 4,5-dibromopent-1-yne: Why does bromination of the double bond occur selectively?
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1answer
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What is the stereochemistry resulting from hydroboration of 1-methylcyclopentene?

What is the major product of the following reaction sequence? I'm supposed to work out the structures of both 2 and 3, but I already know 2 to be 1-methylcyclopentene (as the most substituted ...
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2answers
846 views

Getting 3,4-dimethylhex-3-ene from but-2-ene

How can one get 3,4-dimethylhex-3-ene from but-2-ene ? $\hskip2in$ Using $\ce{Br_2}$ then two equivalents of $\ce{CH_3CH_2MgBr}$, I can get the corresponding alkane (3,4-dimethylhexane) but I don't ...
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1answer
373 views

Addition reaction of hydroiodic acid to 2-bromo-3-chloro-2-butene

How can the major product of the addition reaction of 2-bromo-3-chloro-2-butene with hydroiodic acid be predicted, since Markovnikov's rule fails to distinguish it? $$\ce{H3C-C(Cl)=C(Br)-CH3~+~HI~-&...
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2answers
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What are the products of the reaction of 1-methoxycyclohexene with dilute hydrochloric acid?

When 1-methoxycyclohexene is treated with dilute aqueous hydrochloric acid, methanol is produced along with another organic product. Identify this product. Explain why methoxycyclohexane is inert ...
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1answer
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What is the difference between “bromine” and “bromine water” in their reaction with an alkene?

In question 16 of the A-Level Chemistry 2013 exam, there is this reaction scheme: $$\ce{CH3CH=CH2 ->[?] CH3-CHBr-CH2Br}$$ The question asks for both the name of the reagent and the product. I ...
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2answers
948 views

Hydroboration/oxidation vs acid-catalyzed hydration of 1-phenylpropene

I am trying to predict the products of both the hydroboration/oxidation and acid-catalyzed hydration of 1-phenylpropene: Both C1 and C2 of the double bond are secondary carbons. However, I have the ...
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1answer
613 views

What is Markovnikov's rule?

What is Markovnikov's rule? How can we use it to predict the products of additions to alkenes? And is it always obeyed, or are there exceptions to this rule?
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1answer
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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. $\ce{(p-NO2Ph)_2CO}$ $\ce{(CH3)_2CO}$ $\ce{(p-NO2Ph)COH}$ $\...
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1answer
630 views

Regioselectivity in Kharasch addition of bromotrichloromethane

When hex-1-ene is treated with bromotrichloromethane in the presence of a peroxide initiator (e.g. dibenzoyl peroxide), what is the regioselectivity of the addition? I know that the radical addition ...
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1answer
195 views

Products for the hydrogenation of the cycloalkene in (3R,4R,5S)-4,5-diamino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic acid

Write the products (more than one) for the hydrogenation of the cycloalkene ring in (3⁠R,4⁠R,5⁠S)-4,5-diamino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic acid. Reagents are molecular hydrogen with ...
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1answer
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Resonance in carbocation derived from allenes

During a reaction if addition on one of the $\pi$ bonds of an allene (containing even number of $\pi$ bonds like $\ce {H2C=C=CH2}$) takes place then a carbocation is formed. To decide the position of ...