What is the product when $C_6H_5CH_2NH_2$ reacts with $HNO_2$?

> [!TLDR] > The reaction of benzylamine ($C_6H_5CH_2NH_2$) with nitrous acid ($HNO_2$) proceeds via diazotization followed by spontaneous decomposition to give benzyl alcohol ($C_6H_5CH_2OH$) as the major product, along with nitrogen gas. ## Concept and Intuition This question tests your understanding of **nucleophilic substitution reactions** — specifically, the reaction of primary amines with nitrous acid. The key here is that $HNO_2$ is unstable and generated *in situ* (usually from NaNO₂ + dilute HCl). It reacts with a primary amine to form a **diazonium salt**. But here’s the critical distinction: - **Aromatic primary amines** (like aniline, $C_6H_5NH_2$) form stable diazonium salts at low temperatures (0–5°C), which can be used in coupling reactions. - **Aliphatic primary amines** (like benzylamine, $C_6H_5CH_2NH_2$) form highly unstable diazonium salts that immediately decompose, even at low temperatures, to give a **carbocation** — and then a mixture of products. Benzylamine is special because it’s a **benzylic primary amine**: the $–CH_2NH_2$ group is attached directly to a benzene ring. The resulting carbocation ($C_6H_5CH_2^+$) is resonance-stabilized, making it relatively stable and leading to a cleaner product than with simple alkyl amines. > [!WARNING] > A common mistake is to treat benzylamine like an aromatic amine and expect a stable diazonium salt. Remember: the $–NH_2$ group is on an $sp^3$ carbon, not directly on the ring — so it behaves as an **aliphatic** primary amine, not an aromatic one. ## Step-by-Step Solution **1. Formation of nitrous acid** $HNO_2$ is prepared in the reaction mixture by mixing sodium nitrite with a dilute acid (typically HCl or $H_2SO_4$): $$NaNO_2 + HCl \rightarrow HNO_2 + NaCl$$ **2. Diazotization of benzylamine** The primary amine group reacts with $HNO_2$ to form an **unstable diazonium salt**: $$C_6H_5CH_2NH_2 + HNO_2 + HCl \rightarrow [C_6H_5CH_2N_2^+Cl^-] + 2H_2O$$ This is the same type of reactio

What is the product when C₆H₅CH₂NH₂ reacts with HNO₂?

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C_6H_5CH_2NH_2

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Concept understanding — Nucleophilic Substitution Reactions

Nucleophilic Addition – From Intuition to Precision

Imagine you have a molecule with a carbon–oxygen double bond — a carbonyl group ( $\ce{C=O}$ ). That oxygen is greedy for electrons; it pulls them away from carbon, leaving the carbon slightly positive ( $\delta^+$ ) and the oxygen slightly negative ( $\delta^-$ ). Now, if you bring a species that is rich in electrons (a nucleophile, meaning "nucleus-loving"), it will naturally be attracted to that electron-deficient carbon. The nucleophile attacks the carbon, the $\pi$ bond breaks, and the oxygen picks up a proton (or some other electrophile) to become stable. That, in a nutshell, is nucleophilic addition.

Note

The key idea: a nucleophile adds across a polar multiple bond (usually $\ce{C=O}$ or $\ce{C≡N}$ ), breaking the $\pi$ bond and forming two new sigma bonds.

The Precise Statement

Nucleophilic addition is a reaction in which a nucleophile (an electron-rich species) forms a sigma bond with an electrophilic carbon atom of a polar multiple bond (typically a carbonyl group, $\ce{C=O}$ , or a nitrile, $\ce{C≡N}$ ), while the $\pi$ bond breaks. The resulting intermediate then captures a proton (or another electrophile) to give a neutral product.

In general form:

\ce{R2C=O + Nu^- ->[H^+] R2C(OH)Nu}

The nucleophile ( $\ce{Nu^-}$ ) attacks the carbonyl carbon; the oxygen becomes negatively charged; then a proton ( $\ce{H^+}$ ) from the medium attaches to the oxygen, yielding an alcohol.

Why It Happens – The Driving Force

The carbonyl carbon is electrophilic because:

Oxygen is more electronegative than carbon, so the $\ce{C=O}$ bond is polarised: $\ce{C^{\delta+}=O^{\delta-}}$ .
The $\pi$ bond is weaker than a $\sigma$ bond, so it can break relatively easily.

A nucleophile (like $\ce{OH^-}$ , $\ce{CN^-}$ , or $\ce{NH3}$ ) has a lone pair or a negative charge. It seeks positive centres. The attack forms a new $\sigma$ bond, and the $\pi$ electrons move entirely to oxygen, creating an alkoxide ion ( $\ce{R2C-O^-}$ ). This intermediate is then quenched by a proton.

Watch out

A common mistake: thinking the nucleophile attacks the oxygen. No — oxygen is already electron-rich; the nucleophile goes to the carbon because it is electron-deficient.

A Concrete Example – Addition of HCN to a Ketone

Take acetone ( $\ce{CH3COCH3}$ ) and hydrogen cyanide ( $\ce{HCN}$ ). In the presence of a base, $\ce{CN^-}$ (the nucleophile) attacks the carbonyl carbon:

\ce{CH3COCH3 + CN^- -> CH3C(O^-)(CN)CH3}

The alkoxide intermediate then picks up a proton from $\ce{HCN}$ (or from water) to give a cyanohydrin:

\ce{CH3C(O^-)(CN)CH3 + H^+ -> CH3C(OH)(CN)CH3}

The product is acetone cyanohydrin. Notice: two new sigma bonds formed ( $\ce{C-CN}$ and $\ce{O-H}$ ), and the $\pi$ bond is gone.

What Makes a Good Nucleophile?

Strong nucleophiles are usually negatively charged or have lone pairs:

$\ce{OH^-}$ , $\ce{CN^-}$ , $\ce{NH2^-}$ , $\ce{CH3O^-}$ , $\ce{H^-}$ (from hydride reagents like $\ce{NaBH4}$ or $\ce{LiAlH4}$ )
Neutral but polarisable: $\ce{NH3}$ , $\ce{H2O}$ (weaker, but can add under acidic conditions) …

Why this formula?

Nucleophilic Substitution Reactions: Why the Key Formulas Hold

Nucleophilic substitution reactions are a cornerstone of organic chemistry. Instead of just memorizing the rate laws, let's understand why they arise from the molecular events.

1. The Two Main Mechanisms: A Tale of Timing

The key formulas (rate laws) for nucleophilic substitution come directly from how many molecules are involved in the rate-determining step (RDS) — the slowest step that controls the overall reaction speed.

SN1: Unimolecular — The Leaving Group Goes First

The Rate Law:

\text{Rate} = k[\text{RX}]

Why?

The reaction happens in two steps:

Slow step (RDS): The C–X bond breaks spontaneously, forming a carbocation intermediate. Only the substrate ( $\text{RX}$ ) is involved.

\text{RX} \xrightarrow{\text{slow}} \text{R}^+ + \text{X}^-

Fast step: The nucleophile ( $\text{Nu}^-$ ) attacks the carbocation.

\text{R}^+ + \text{Nu}^- \xrightarrow{\text{fast}} \text{RNu}

Since the slow step depends only on the concentration of $\text{RX}$ , the rate law has no dependence on $[\text{Nu}^-]$ . The nucleophile arrives after the carbocation is formed — it cannot affect the speed of the first step.

Key insight: The rate is determined by how easily the leaving group leaves, not by how fast the nucleophile attacks.

SN2: Bimolecular — Simultaneous Attack and Departure

The Rate Law:

\text{Rate} = k[\text{RX}][\text{Nu}^-]

Why?

The reaction occurs in one concerted step:

The nucleophile attacks the carbon from one side at the same time as the leaving group departs from the opposite side.
Both $\text{RX}$ and $\text{Nu}^-$ must collide with the correct orientation and sufficient energy.

The rate depends on the frequency of productive collisions between the two molecules. This is directly proportional to the product of their concentrations:

\text{Rate} \propto [\text{RX}] \times [\text{Nu}^-]

Key insight: Both partners are involved in the transition state simultaneously — if either is missing, the reaction cannot proceed.

2. The Transition State: Why the Formulas Are Not Just "Given"

For SN2, the transition state has a pentavalent carbon (five bonds partially formed/broken). The energy barrier depends on steric hindrance — bulkier groups around carbon make it harder for the nucleophile to approach, which is why SN2 is favored at primary carbons. …

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The reaction of benzylamine ( $C_6H_5CH_2NH_2$ ) with nitrous acid ( $HNO_2$ ) proceeds via diazotization followed by spontaneous decomposition to give benzyl alcohol ( $C_6H_5CH_2OH$ ) as the major product, along with nitrogen gas.

Concept and Intuition

This question tests your understanding of nucleophilic substitution reactions — specifically, the reaction of primary amines with nitrous acid. The key here is that $HNO_2$ is unstable and generated in situ (usually from NaNO₂ + dilute HCl). It reacts with a primary amine to form a diazonium salt.

But here’s the critical distinction:

Aromatic primary amines (like aniline, $C_6H_5NH_2$ ) form stable diazonium salts at low temperatures (0–5°C), which can be used in coupling reactions.
Aliphatic primary amines (like benzylamine, $C_6H_5CH_2NH_2$ ) form highly unstable diazonium salts that immediately decompose, even at low temperatures, to give a carbocation — and then a mixture of products.

Benzylamine is special because it’s a benzylic primary amine: the $–CH_2NH_2$ group is attached directly to a benzene ring. The resulting carbocation ( $C_6H_5CH_2^+$ ) is resonance-stabilized, making it relatively stable and leading to a cleaner product than with simple alkyl amines.

Watch out

A common mistake is to treat benzylamine like an aromatic amine and expect a stable diazonium salt. Remember: the $–NH_2$ group is on an $sp^3$ carbon, not directly on the ring — so it behaves as an aliphatic primary amine, not an aromatic one.

Step-by-Step Solution

1. Formation of nitrous acid

$HNO_2$ is prepared in the reaction mixture by mixing sodium nitrite with a dilute acid (typically HCl or $H_2SO_4$ ):

NaNO_2 + HCl \rightarrow HNO_2 + NaCl

2. Diazotization of benzylamine

The primary amine group reacts with $HNO_2$ to form an unstable diazonium salt:

C_6H_5CH_2NH_2 + HNO_2 + HCl \rightarrow [C_6H_5CH_2N_2^+Cl^-] + 2H_2O

This is the same type of reaction as with any primary amine — the $–NH_2$ group is converted to $–N_2^+$ .

3. Spontaneous decomposition

Unlike aromatic diazonium salts, this aliphatic diazonium salt is extremely unstable and decomposes instantly, even at 0°C, releasing nitrogen gas:

[C_6H_5CH_2N_2^+] \rightarrow C_6H_5CH_2^+ + N_2 \uparrow

The loss of $N_2$ is driven by the formation of an extremely stable $N\equiv N$ triple bond.

4. Carbocation reacts with water …

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The Reaction

The compound is benzylamine ( $C_6H_5CH_2NH_2$ ).

When treated with nitrous acid ( $HNO_2$ ), the product is benzyl alcohol ( $C_6H_5CH_2OH$ ), along with nitrogen gas ( $N_2$ ).

Why?

Benzylamine is a primary aliphatic amine (the $NH_2$ is attached to a $CH_2$ group, not directly to the benzene ring).

$HNO_2$ converts primary aliphatic amines into diazonium salts, which are unstable and spontaneously decompose to give a carbocation. This carbocation reacts with water to form an alcohol.

The balanced equation:

C_6H_5CH_2NH_2 + HNO_2 \rightarrow C_6H_5CH_2OH + N_2 + H_2O

Common Mistakes & How to Avoid Them

1. ✗ Mistaking benzylamine for an aromatic amine

Error: Students think the $NH_2$ is attached directly to the benzene ring (like aniline), so they predict a diazonium salt as the product.
Why it’s wrong: In benzylamine, the $NH_2$ is on a side chain — it’s aliphatic, not aromatic. Aromatic diazonium salts are stable at low temperatures; aliphatic ones decompose instantly.
How to avoid: Always check where the $NH_2$ is attached. If it’s on a carbon that is part of an alkyl chain (even if that chain is attached to a ring), treat it as aliphatic.

2. ✗ Forgetting that $N_2$ gas is released

Error: Writing only the alcohol as the product, omitting nitrogen gas.
Why it’s important: $N_2$ evolution is a key test for primary aliphatic amines — it’s often asked in exams.
How to avoid: Memorize: primary aliphatic amine + $HNO_2$ → alcohol + $N_2$ + $H_2O$ . Always include $N_2$ in the product list.

3. ✗ Writing the wrong alcohol

Error: Writing phenol ( $C_6H_5OH$ ) instead of benzyl alcohol.
Why it’s wrong: The carbocation forms on the $CH_2$ group, not on the ring. Water attacks that carbon, giving $C_6H_5CH_2OH$ .
How to avoid: Track the carbon that originally held the $NH_2$ — that’s where the $OH$ ends up.

4. ✗ Confusing with the reaction of aniline

Error: Applying the same logic as for aniline ( $C_6H_5NH_2$ ), which gives a stable diazonium salt at 0–5°C.
Why it’s wrong: Aniline is an aromatic primary amine — its diazonium salt is stable in cold conditions. Benzylamine is aliphatic, so no stable diazonium salt forms.
How to avoid: Distinguish clearly:
- Aromatic primary amine → stable diazonium salt (cold) …

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Same / Similar Concept — real previous-year questions on the same or a closely similar concept, not this exact question.

AP EAPCET 2026Set eng-2026-05-12-FN1 markMCQ
$\mathrm{CH_3CH_2CH_2Cl}$
›Reveal solutionSolution
Two independent routes correctly build n-propylamine (nitro reduction of 1-chloropropane, and nitrile chain-extension + reduction of chloroethane); the Hofmann degradation route instead shortens the chain by one carbon, giving ethylamine.

Concept and Intuition

Three very different strategies for making primary amines are being tested, and the key discipline is to count carbons through each transformation, since some routes preserve chain length and one (Hofmann bromamide degradation) deliberately removes a carbon.

$\mathrm{AgNO_2}$ vs $\mathrm{NaNO_2}$ : nitrite is an ambident nucleophile (can attack through O or N). With the softer, more covalent silver salt $\mathrm{AgNO_2}$ , alkylation occurs preferentially through nitrogen, giving the nitroalkane as the major product (with $\mathrm{NaNO_2}$ , the ionic character favours O-alkylation, giving the alkyl nitrite instead). Reducing a nitroalkane ( $\mathrm{Fe/HCl}$ ) gives the primary amine with the same carbon skeleton.

The cyanide route ( $\mathrm{NaCN}$ , then reduction) is a classic chain-extension: the nucleophilic $\mathrm{CN^-}$ displaces the halide, adding one carbon to the chain as a nitrile, and reducing the nitrile ( $\mathrm{H_2/Ni}$ or $\mathrm{LiAlH_4}$ ) gives a primary amine that is one carbon longer than the starting halide.

The Hofmann bromamide degradation ( $\mathrm{Br_2/OH^-}$ on an amide) is the opposite: it removes the carbonyl carbon (as it leaves via an isocyanate/carbamate intermediate that loses $\mathrm{CO_2}$ ), giving a primary amine with one carbon fewer than the starting amide.

Step-by-Step Solution

I: $\mathrm{CH_3CH_2CH_2Cl}$ (3 carbons) + $\mathrm{AgNO_2}$ → $\mathrm{CH_3CH_2CH_2NO_2}$ (1-nitropropane, N-alkylation favoured by the covalent Ag–N bond). + $\mathrm{Fe/HCl}$ (reduction) → $\mathrm{CH_3CH_2CH_2NH_2}$ = n-propylamine. Matches. …
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AP EAPCET 2025Set eng-2025-05-22-AN1 markMCQ
$\mathrm{HCl + ZnCl_2}$
›Reveal solutionSolution
Tests why thionyl chloride, not the phosphorus halides, is the preferred reagent purely on the grounds of product purity.

Concept and Intuition

Several reagents convert $R-OH \to R-Cl$ , but "preferred for pure product" is a purity argument, not a yield argument. The reagent of choice is the one whose by-products leave the flask on their own (as gases), so no work-up/purification is needed to remove them from the alkyl chloride.

Step-by-Step Solution

$R-OH + HCl/ZnCl_2 \to R-Cl + H_2O$ (Lucas reagent) — works well only for tertiary/some secondary alcohols and leaves $ZnCl_2$ /water behind.

$R-OH + PCl_5 \to R-Cl + POCl_3 + HCl$ — the by-product $POCl_3$ is a liquid that must be removed by distillation, contaminating the crude product.

$R-OH + PCl_3 \to R-Cl + H_3PO_3$ — leaves phosphorous acid behind, again needing separation.

$3R-OH + SOCl_2 \to R-Cl + SO_2\uparrow + HCl\uparrow$ — both by-products are gases that simply bubble out, so the alkyl chloride is obtained directly in pure form with essentially no work-up. …
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AP EAPCET 2025Set eng-2025-05-23-FN1 markMCQ
$Q. The reaction of benzene diazonium chloride with Cu and HCl is known as (A) Sandmeyer reaction (B) Etard reaction (C) Finkelstein reaction (D) Gattermann reaction$
›Reveal solutionSolution
This distinguishes the Sandmeyer reaction (uses cuprous salts, e.g. $Cu_2Cl_2/Cu_2Br_2$ ) from the closely related Gattermann reaction (uses copper powder directly with HCl/HBr) for converting a diazonium salt to an aryl halide.

Concept and Intuition

Both reactions replace the diazonium group ( $-N_2^+$ ) with a halogen via a radical/copper-mediated mechanism, and both give the same type of product (aryl halide + $N_2$ ). The distinguishing feature examiners test is the reagent form: Sandmeyer's reaction historically uses a cuprous halide salt (e.g. $Cu_2Cl_2$ ) generated in situ or added directly, while the Gattermann reaction is the simplified variant that uses copper powder (metallic Cu) together with the corresponding hydrohalic acid (HCl/HBr) — no cuprous salt needed.

Step-by-Step Solution

The reaction described is $ArN_2^+Cl^-$ treated with Cu (metal powder) and HCl.

Because the copper source is elemental copper powder (not a cuprous salt like $Cu_2Cl_2$ ), this specific reagent combination is named the Gattermann reaction, distinguishing it from the Sandmeyer reaction (which specifically uses cuprous chloride/cuprous bromide). …
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AP EAPCET 2023Set ap-2023-05-23-AN1 markMCQ
$\mathrm{(CH_3)_2CHCH_2NH_2 + HCOOH}$
›Reveal solutionSolution
Isonitrile hydrolysis always gives the corresponding primary amine (with the SAME alkyl group as the isonitrile) plus formic acid — the alkyl group itself is never altered.

Concept and Intuition

An isocyanide, $R-N\equiv C$ , is hydrolysed under acidic aqueous conditions by nucleophilic attack of water at the terminal carbon, ultimately cleaving the C–N bond to release the alkyl group AS AN AMINE (with its nitrogen intact, unchanged connectivity to R) while the isocyanide carbon (originally bonded only to N and nothing else besides the lone pair/triple bond) ends up as formic acid, HCOOH. This is a key distinguishing test reaction of isocyanides vs their isomeric nitriles (which hydrolyse differently, to carboxylic acids + ammonia/amine on the OTHER side).

Step-by-Step Solution

Isobutyl isonitrile: $(CH_3)_2CHCH_2-N\equiv C$ — the isobutyl group ( $(CH_3)_2CHCH_2-$ ) is attached to the isocyanide nitrogen.

Acid-catalysed hydrolysis proceeds: $R-NC + 2H_2O \xrightarrow{H^+} R-NH_2 + HCOOH$ .

Applying this to isobutyl isonitrile: the alkyl group R = $(CH_3)_2CHCH_2-$ ends up as the primary amine $(CH_3)_2CHCH_2NH_2$ (isobutylamine), retaining the exact same carbon skeleton and nitrogen attachment. …
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AP EAPCET 2022Set eng-2022-07-04-FN1 markMCQ
$\mathrm{CH_3CH_2CH_2CH_2OH}$
›Reveal solutionSolution
Aqueous KOH gives substitution (1-butanol); alcoholic KOH gives elimination, and since only C2 has beta-hydrogens, the only possible alkene is but-1-ene.

Concept and Intuition

Alkyl halides react differently depending on the solvent/base used: aqueous KOH (with water as solvent) favours $S_N2$ nucleophilic substitution because $\mathrm{OH^-}$ acts predominantly as a nucleophile in the polar protic medium, while alcoholic KOH (KOH dissolved in ethanol, with much less free water) favours $E2$ elimination, as the base character of $\mathrm{OH^-}$ /ethoxide dominates, abstracting a beta-hydrogen to form an alkene.

Step-by-Step Solution

Substrate: 1-chlorobutane, $\mathrm{CH_3CH_2CH_2CH_2Cl}$ -- a primary alkyl halide, Cl on C1.

Aqueous KOH: favours $S_N2$ substitution (primary halides are ideal $S_N2$ substrates -- unhindered backside attack). $\mathrm{OH^-}$ displaces $\mathrm{Cl^-}$ directly: product P = $\mathrm{CH_3CH_2CH_2CH_2OH}$ (1-butanol).

Alcoholic KOH: favours E2 elimination. The base removes a beta-hydrogen (a hydrogen on the carbon adjacent to the one bearing Cl).

In 1-chlorobutane, C1 bears Cl; the only carbon adjacent to C1 is C2 -- so the only beta-hydrogens available are those on C2. There is no other beta-carbon (C1 is a terminal/primary carbon), so there is only one possible elimination direction. …
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AP EAPCET 2021Set eng-2021-08-25-AN1 markMCQ
$CH_3Cl \xrightarrow{KCN} (A) \xrightarrow{H^+/H_2O} (B)$
›Reveal solutionSolution
$CH_3Cl$ with $KCN$ forms methyl cyanide, and acidic hydrolysis of that nitrile gives acetic acid.

Concept and Intuition

Potassium cyanide, being an ionic (predominantly carbon-nucleophilic) source of $CN^-$ , substitutes alkyl halides via their carbon end to give alkyl cyanides (nitriles), $R$ – $C\equiv N$ , rather than isocyanides. Nitriles are the functional equivalent of a "masked carboxylic acid" — acidic (or basic) hydrolysis converts the $C\equiv N$ group all the way to $-COOH$ (via an amide intermediate).

Step-by-Step Solution

$CH_3Cl + KCN \rightarrow CH_3CN + KCl$ — this is $(A)$ , methyl cyanide (acetonitrile).

Acidic hydrolysis of a nitrile: $CH_3CN + 2H_2O \xrightarrow{H^+} CH_3COOH + NH_3$ (via the amide $CH_3CONH_2$ intermediate).

So $(B) = CH_3COOH$ (acetic acid).

Common Mistakes …
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Q.What is the product when $C_6H_5CH_2NH_2$ reacts with $HNO_2$ ?

Concept understanding — Nucleophilic Substitution Reactions

Nucleophilic Addition – From Intuition to Precision

The Precise Statement

Why It Happens – The Driving Force

A Concrete Example – Addition of HCN to a Ketone

What Makes a Good Nucleophile?

Why this formula?

Nucleophilic Substitution Reactions: Why the Key Formulas Hold

1. The Two Main Mechanisms: A Tale of Timing

SN1: Unimolecular — The Leaving Group Goes First

SN2: Bimolecular — Simultaneous Attack and Departure

2. The Transition State: Why the Formulas Are Not Just "Given"

Concept and Intuition

Step-by-Step Solution

Concept: Diazotisation & Sandmeyer Reaction / Decomposition of Primary Amines

Why this method?

Steps of the method:

The Reaction

Common Mistakes & How to Avoid Them

1. ✗ Mistaking benzylamine for an aromatic amine

2. ✗ Forgetting that $N_2$ gas is released

3. ✗ Writing the wrong alcohol

4. ✗ Confusing with the reaction of aniline

Concept and Intuition

Step-by-Step Solution

Concept and Intuition

Step-by-Step Solution

Concept and Intuition

Step-by-Step Solution

Concept and Intuition

Step-by-Step Solution

Concept and Intuition

Step-by-Step Solution

Concept and Intuition

Step-by-Step Solution

Common Mistakes …

Q.What is the product when C6H5CH2NH2C_6H_5CH_2NH_2C6​H5​CH2​NH2​ reacts with HNO2HNO_2HNO2​?

Concept and Intuition

Step-by-Step Solution

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Q.What is the product when $C_6H_5CH_2NH_2$ reacts with $HNO_2$ ?

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