What are Reactive Intermediates?

In chemistry, reactive intermediates are termed as short-lived, highly reactive atoms with high energy. They rapidly transform into stable particles during a chemical reaction. In specific cases, by means of matrix isolation and at low-temperature reactive intermediates can be isolated.

Introduction to Reactive Intermediates

Reactive intermediates are formed in the intermediate step on account of a chemical reaction. It contrasts with normal reaction intermediates just through quick spectrographic strategies. Spectroscopy is the research of the connection between electromagnetic radiation and substances. They are arranged depending on the kind of radiative energy utilized in the association.

Reactive intermediates extinction can be demonstrated with the assistance of element trapping. The chemical element trap is a compound that recognizes an atom in specific cases, and they are represented beneath:

  • At the point, when the particle is exceptionally reactive or when it can't be found by spectroscopic research.
  • At the point, when the concentration of the molecule is as far as possible from the finding limit.
  • At the point, when a particle is available inside the mixture, where components of a component intervene with its identification.
  • It is difficult to recognize intermediate from its transition state. It is an expression that relates to expected energy at a more significant level alongside a reaction coordinate. It is a kind of reaction that includes a specific configuration.


A particle with a positively charged carbon molecule is termed carbocation. Methenium CH3+, methanium CH5+, and ethanium C2H7+ are some of the simplest examples of the carbocation. The additional name of the carbocation is carbonium ions. Carbonium ions are classified into two categories depending on the valence of the carbon atom,

  • +3 in carbenium particles (protonated carbenes).
  • +5 or +6 in the carbonium particles (protonated alkanes, named by similarity to ammonium). These are considerably less normal.

Structure and properties

The charged carbon particle in a carbonium is a sextet, for example it has just six electrons in its external valence shell rather than the eight electrons in the outer shell that guarantees octet rule. Thusly, carbonium ions are commonly reactive, trying to pack the octet of valence electrons just as recapture a neutral charge. The carbonium ion has sp3 hybridization with a void sp3orbital with positive charge. Be that as it may, the reactivity of a carbonium ion more intently takes after a trigonal planar structure with sp2 hybridization. Example: methenium ion.


The diagram shows the stability of carbocations

The order of stability is 30>20>10, just as the methyl cation. The methyl cation is so unsteady it is just seen in the gas stage.

Carbocations are regularly attacked by nucleophiles like water or halide particles. Thus, they are objective to nucleophilic attack.

Cations such as allyl carbonium CH2=CH-CH2+ and benzyl carbonium C6H5-CH2+ are steadier than most other carbonium ions. Particles that can frame benzyl or allyl carbonium are particularly reactive. These carbonium where the C+ is neighboring another carbon particle that has a pi bonds have additional solidness in view of the cross-over of the unfilled p orbital of the carbonium ion with the p orbitals of the π bond. This cross-over of the orbitals permits the charge delocalization and, consequently, stabilize out the carbocation.


Carbanion can be characterized as a negatively charged particle in which a carbon molecule displays trivalence and holds a conventional negative charge whose extent is at the point, when pi delocalization doesn't happen in the natural, carbanions commonly expect to be a bowed, straight, or three-sided pyramidal structure.

In all carbanions, the electron thickness is highly assembled at the negatively charged carbon atom. Along these lines, this carbon turns into an optimal place of attack for some electron-inadequate species.

The diagram shows the resonance of carbanions

An explanation specifying the conceivable resonance constructions of a carbanion in which the carbon holding the negative charge is bound to three distinct alkyls or aryl groups or hydrogen is given previously.

Factors affecting carbanion stability

Generally, carbanions act as nucleophiles and their pH is generally over 7. The nucleophilicity and the basicity of the carbanion are typically controlled by the substituents that are connected to the carbon. Just like the case with most charged carbon species, the substituent can either increase or diminish the steadiness of the particle in general. The most important factor while considering the stability of carbanions is dependent on the substituent attached.

  • The inductive effect, by means of which profoundly electronegative substituent combined to the carbanion assist with subdueing the negative charge on it and make the atom more steady. Then again, profoundly electropositive substituent can build the negative charge on the carbanion and, subsequently, decline the stability of the atom.
  • The resonance effect, through which the electron delocalization disseminates the negative charge all around the carbanion, adding stability. Aromatic compounds add a lot of steadiness to carbanions when they are available as a substituent because of the resonance effect.

Free Radicals

Free radicals are atoms that have unpaired electrons on their outermost shell. They are exceptionally reactive towards different substances. Atoms of free radicals will suddenly dimerize or polymerize if they interact with one another. They are sensibly steady just at extremely low concentrations in inactive media or a vacuum. A prominent illustration of a free radical is hydroxyl radical. Hydroxyl radical is a particle that is one hydrogen atom of water and accordingly has one bond hanging from the oxygen.

Radicals might be made in various manners, incorporating combinations with extremely weak or tenuous reagents, reactions at exceptionally low down temperatures, or separation of bigger particles.


Free radical alkyl intermediates are stabilized out by comparable actual cycles to carbocations: when in doubt, the more substituted free radical center is the more stable center. This coordinates the radical reactions. Hence, the structure of a tertiary radical is preferred over secondary which is preferred over the primary. Similarly, radicals close to functional groups like carbonyl, nitrile, and ether are steadier than tertiary alkyl radicals.

The diagram shows the stability of free radicals


A carbene R=C is a particle containing a neutral carbon with a valence of two and two unshared electrons in its outermost shell. The expression carbene may likewise allude to the particular compound H2C , additionally called methylene, the parent hydride from which any remaining carbene compounds are officially determined.

Singlet and tripet carbenes

Carbenes are called singlet or triplets relying upon the spins of the electrons they have. Singlet carbenes are spin paired carbenes while triplet carbenes have two unpaired electrons. Singlet carbene adopts a sphybridization and the triplet might be either sp or sphybridization. Carbenes with two unpaired electrons are stable in the vaporous state, while carbenes with spin-paired electrons are regularly stable in watery media.

The diagram shows the singlet and triplet carbenes


Carbenes show different reactivity. The reactivity of a specific carbene depends upon the substituent. The reactivity of carbenes can be influenced by metals. Carbenes can be named nucleophilic, electrophilic, or amphiphilic.

Context and Applications

This topic is important for both postgraduate and undergraduate courses particularly for Bachelors and Masters of chemistry.

Practice Problems

Question 1: Among the given carbocation find out the most stable carbocation:

The diagram shows the various carbocations

Answer: The correct answer is b.

Explanation: The carbonium ion given in option b is more stable than others because of the extended conjugation. The larger hyperconjugation stabilization is due to the increased number of neighboring methyl groups.

IQuestion 2: What is the hybridization of carbocation?
a) sp
b) sp2
c) sp3
d) sp3d
Answer: The correct answer is b.
Explanation: The hybridization of the carbocation is sp2. A carbocation is a molecule in which a carbon atom bears three bonds and a positive charge.

Question 3: On what basis the stability of free radical is explained?
a) Inductive effect
b) Electromeric effect
c) Hyperconjugation
d) Mesomeric effect
Answer: The correct answer is c.
Explanation: Stability of free radicals can be explained on the basis of hyperconjugation effect and ease of formation.

Question 4: Carbonium ions are the intermediates in which the positive charge is carried by the carbon atom with how many electrons in the valence shell.
a) 6
b) 5
c) 4
d) 3
Answer: The correct answer is a.
Explanation: Carbonium ions are the intermediates in which the positive charge is carried by the carbon atom with six electrons in the valence shell. It is an organic cation in which the positive charge is located on a carbon atom.

Question 5: Which of the following free radical has the maximum ease of formation?
a) 10
b) 20
c) 30
d) CH3
Answer: The correct answer is c.
Explanation: 30 free radical has the maximum ease of formation. Free radicals do not carry any charge.

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