Chemistry of Isocyanides and Cyanides
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Questions and Answers

Which reaction produces a secondary amine from an isocyanide?

  • RCN + 2H<sub>2</sub>O → RCOOH + NH<sub>3</sub>
  • R-C≡N + 4[H] SnCl<sub>2</sub>/HCl → RCH<sub>2</sub>NH<sub>2</sub>
  • R-NEC + 4[H] SnCl<sub>2</sub>/HCl → CH<sub>3</sub>NH<sub>2</sub> (correct)
  • R-C≡N + R-Mg-X → R-C=N-MgX

Alkyl isocyanide undergoes the Stephen reaction.

False (B)

What is the general formula of alkyl cyanide?

R-C≡N

In acidic medium, alkyl cyanide hydrolyzes to form __________ and __________.

<p>carboxylic acid, ammonia</p> Signup and view all the answers

Match the following properties with either Alkyl Cyanide or Alkyl Isocyanide:

<p>Thermal Stability = Alkyl Cyanide Produces primary amine upon hydrolysis = Alkyl Isocyanide React with Grignard reagent = Alkyl Cyanide Method of preparation includes carbyl amine reaction = Alkyl Isocyanide</p> Signup and view all the answers

What is the product of hydrolyzing alkyl cyanide in acidic medium?

<p>Carboxylic acid and ammonia (D)</p> Signup and view all the answers

Isocyanides can react with Grignard reagents.

<p>False (B)</p> Signup and view all the answers

What is the IUPAC name for methyl isocyanide?

<p>Methane isonitrile</p> Signup and view all the answers

The general formula for isocyanides is R-NC, where R represents the __________ group.

<p>alkyl</p> Signup and view all the answers

Which of the following statements about cyanide usage is true?

<p>Cyanide is used in metallurgy for electroplating. (B)</p> Signup and view all the answers

Match the following compounds with their corresponding common names:

<p>CH3-NC = Methyl isocyanide CH3-CH2-NEC = Ethyl isocyanide C3H7-NC = Propyl isocyanide</p> Signup and view all the answers

The hydrolysis of isocyanides produces secondary amines.

<p>False (B)</p> Signup and view all the answers

What happens to less stable alkyl isocyanides when they are heated?

<p>They convert into more stable alkyl cyanides.</p> Signup and view all the answers

Cyanide is formed from the reaction of alkyl halide with AgCN.

<p>True (A)</p> Signup and view all the answers

The common name for C4H9CN is __________.

<p>Butyl cyanide</p> Signup and view all the answers

Match the following cyanides with their corresponding common names:

<p>CH<sub>3</sub>CN = Methyl cyanide C<sub>2</sub>H<sub>5</sub>CN = Ethyl cyanide C<sub>3</sub>H<sub>7</sub>CN = Propyl cyanide C<sub>5</sub>H<sub>11</sub>CN = Pentyl cyanide</p> Signup and view all the answers

Which of the following is a method for preparing cyanide from acid amide?

<p>RCONH<sub>2</sub> + P<sub>2</sub>O<sub>5</sub> (A)</p> Signup and view all the answers

The Mendius reduction reaction converts alkyl cyanide into secondary amines.

<p>False (B)</p> Signup and view all the answers

What is produced when alkyl isocyanide undergoes reduction in the presence of SnCl2/HCl?

<p>Secondary amine</p> Signup and view all the answers

What is formed when aniline is heated with KOH and CHCl3?

<p>Phenyl isocyanide (C)</p> Signup and view all the answers

Secondary amines give diazotization reactions.

<p>False (B)</p> Signup and view all the answers

What compound is produced from the Gatterman reaction?

<p>Aniline</p> Signup and view all the answers

The coupling reaction between aromatic amines and diazonium salts forms ______.

<p>azo dyes</p> Signup and view all the answers

Match the following reactions with their products:

<p>Diazotization = Diazonium salt Acetylation = N-acetyl derivative Coupling reaction = Azo compound Nitration = Nitro compound</p> Signup and view all the answers

Which reagent is used to differentiate between primary, secondary, and tertiary amines?

<p>Hinsberg reagent (A)</p> Signup and view all the answers

Aniline turns black when exposed to air.

<p>True (A)</p> Signup and view all the answers

What is oil of mirbane?

<p>Nitrobenzene</p> Signup and view all the answers

Which of the following reactions results in the formation of aniline?

<p>Reduction of nitrobenzene in acidic medium (B)</p> Signup and view all the answers

The Sandmeyer reaction involves the conversion of C6H5NaCl and CuCl/HCl to form C6H5Cl.

<p>True (A)</p> Signup and view all the answers

What is formed when acetamide is heated in the presence of P2O5?

<p>CH3CN</p> Signup and view all the answers

C6H5NH2 + HNO2 0°C → __________.

<p>C6H5N2Cl</p> Signup and view all the answers

Match the following reactions with their correct names:

<p>C6H5NH2 + HNO2 = Diazotisation C6H5NO2 + 6[H] Sn/HCl = Mendius reduction reaction C6H5NaCl + CuCl/HCl = Sandmeyer reaction CH3COOH + NaN3 = Schmidt reaction</p> Signup and view all the answers

What is the product of the Schmidt reaction involving CH3COOH?

<p>CH3NH2 (B)</p> Signup and view all the answers

The reaction C6H5NO2 + 6[H] Sn/HCl yields C6H5NH2 and water.

<p>True (A)</p> Signup and view all the answers

Name the reaction that produces CH3NH2 from CH3COOH and NaN3.

<p>Schmidt reaction</p> Signup and view all the answers

Carbyl amine test gives only _______ amine.

<p>Primary</p> Signup and view all the answers

What is the main product of the reaction of benzoic acid and hydrazoic acid?

<p>Aniline (B)</p> Signup and view all the answers

All aliphatic amines are less basic in nature than ammonia.

<p>False (B)</p> Signup and view all the answers

What is the function of NaOH in the benzylation of amines?

<p>It facilitates the Schotten-Baumann reaction.</p> Signup and view all the answers

Match the following reactions with their outcomes.

<p>C6H5COOH + NaN3 = C6H5NH2 + CO2 + N2 C6H5N=C=S + H2O = Phenol Reduction of nitrobenzene = Aniline Primary amine with CHCl3 and KOH = RNC</p> Signup and view all the answers

The basic nature of amine is due to the presence of _______ on the nitrogen atom.

<p>lone pair of electron</p> Signup and view all the answers

Which of the following statements about aromatic amines is true?

<p>They are insoluble in water. (B)</p> Signup and view all the answers

Trinitro toluene (TNT) is a substance that can be classified as explosive.

<p>True (A)</p> Signup and view all the answers

Flashcards

Alkyl Cyanide (R-CN)

An organic compound containing a -CN (cyano) group directly attached to a carbon atom in an alkyl chain.

Alkane Nitrile

The IUPAC naming system for alkyl cyanides, where the -CN group is considered part of the main carbon chain.

Alkyl Cyanide Synthesis from Alkyl Halides

A reaction using alkyl halides (R-X) and lithium cyanide (LiCN) to synthesize alkyl cyanides.

Alkyl Cyanide Synthesis from Acid Amides

A preparation method for alkyl cyanides using acid amides (RCONH2) and phosphorus pentoxide (P2O5).

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Alkyl Cyanide Synthesis from Diazonium Salts

A reaction where a diazonium salt (C6H5N2Cl) is treated with potassium cyanide (KCN) and copper powder to produce an aryl cyanide.

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Mendius Reduction

A reduction reaction that converts alkyl cyanides (R-CN) into primary amines (RCH2NH2) using reducing agents like SnCl2/HCl or LiAlH4.

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Mendius Reduction of Alkyl Iso Cyanides

A process for producing primary amines from alkyl iso cyanides (R-NC) using reducing agents like SnCl2/HCl.

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Stephen Reduction

A chemical reaction where the partial reduction of alkyl cyanides (R-CN) using SnCl2/HCl produces aldehydes (RCHO).

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Alkyl isocyanide Structure

Alkyl isocyanide is a chemical compound where an alkyl group is attached to a nitrogen atom, which is bonded to a carbon atom via a double bond and a coordinate bond (R-NC).

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Alkyl Isocyanide Preparation

Alkyl isocyanides can be prepared using various methods like the carbylamine reaction, reacting alkyl halides with silver cyanide, using acetamide, or from diazonium salts.

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Reduction of Alkyl Isocyanide

The reaction of an alkyl isocyanide with SnClâ‚‚/HCl (reducing agents) produces a secondary amine. The reaction involves the addition of four hydrogen atoms to the isocyanide group.

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Alkyl Isocyanide Instability

Unlike alkyl cyanides, alkyl isocyanides are unstable and readily decompose upon heating, converting into alkyl cyanides.

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Alkyl Isocyanide and Grignard

Alkyl isocyanides do not react with Grignard reagents, unlike alkyl cyanides, which react to form ketones.

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Stephen Reaction with Nitriles

A reaction where a nitrile (R-C≡N) is reduced to an imine (R-CH=NH) using SnCl2/HCl and hydrogen as the reducing agent.

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Aldimine

An imine formed by the reaction of an aldehyde (R-CHO) with ammonia (NH3).

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Hydrolysis

A reaction where a compound is broken down by the addition of water.

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Isocyanide

An isocyanide is a compound with the functional group -N≡C, where the alkyl group is attached to the nitrogen atom.

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Preparation of Isocyanides from Alkyl Halides

The reaction of alkyl halides with silver cyanide (AgCN) to form alkyl isocyanides.

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Carbylamine Reaction

The reaction of primary amines (RNH2) with chloroform (CHCl3) and potassium hydroxide (KOH) to produce alkyl isocyanides.

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Reaction of Isocyanides with Grignard Reagents

Isocyanides do not react with Grignard reagents.

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Hydrolysis of Isocyanides

Hydrolysis of an isocyanide in acidic medium yields a primary amine and formic acid.

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Sandmeyer Reaction

A reaction that involves the replacement of a diazonium group with a chlorine atom using CuCl/HCl.

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Diazotization

The process of converting a primary aromatic amine to a diazonium salt by reacting it with nitrous acid (HNO2) at low temperatures (0°C).

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Reduction of Nitrobenzene

The reduction of nitrobenzene in acidic medium using Sn/HCl results in the formation of aniline (C6H5NH2).

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Dehydration of Acetamide

The reaction of acetamide with P2O5, which removes water, leads to the formation of acetonitrile (CH3CN).

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Schmidt Reaction

A reaction involving the treatment of a carboxylic acid with sodium azide (NaN3) to yield a primary amine, carbon dioxide, and nitrogen gas.

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Reaction of Primary Amines with Nitrous Acid

The reaction of primary amines with nitrous acid (HNO2) at low temperatures (0°C) to form diazonium salts.

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Ammonolysis of Alkyl Halides

The reaction of alkyl halides with ammonia (NH3) to form primary amines.

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Carbylamine Reaction (or Isocyanide Test)

A reaction where an alkyl halide reacts with an amine to form an isocyanide. This reaction is highly specific to primary amines.

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Coupling Reaction

A reaction involving diazonium salts and phenols or amines. This reaction is used to synthesize azo dyes, which are widely used in coloring fabrics.

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Aldehyde or Ketone reacting with Primary Amine

An organic compound that reacts with primary amines to form a Schiff base. The characteristic reaction occurs with the carbonyl group in aldehydes or ketones.

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Mustard Oil Reaction

A reaction where a primary amine reacts with CS2 and HgCl2 to form a mustard oil (an alkyl isothiocyanate). This reaction is used for detecting primary amines.

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Hinsberg's Reagent

A reagent used to differentiate primary, secondary, and tertiary amines. It is benzene sulphonyl chloride (C6H5SO2Cl).

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Nitrating Mixture

A mixture of concentrated sulphuric acid and concentrated nitric acid used to nitrate aromatic compounds. It acts as a source of nitronium ions (NO2+), the electrophile in the nitration reaction.

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Liebermann Nitrosoamine Test

A test used to identify secondary amines by forming colored nitrosoamines with nitrous acid. The test is named after the chemist who first discovered it.

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Why are amines basic?

The presence of a lone pair of electrons on the nitrogen atom in amines makes them basic. This lone pair can readily accept a proton (H+), making amines act as a base.

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Aromatic amines and water solubility

Aromatic amines (like aniline) are insoluble in water due to their hydrophobic nature. They have a nonpolar aromatic ring, which restricts their solubility in water.

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Schotten-Baumann Reaction

The Schotten-Baumann reaction is a method for benzylating amines in the presence of sodium hydroxide (NaOH) and benzoyl chloride.

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Grignard Reaction with Primary Amines

The reaction of a primary amine with Grignard reagent leads to the formation of an alkane. This reaction acts as a way to convert a primary amine to a simpler hydrocarbon.

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Amatol

Amatol is an explosive mixture composed of TNT (trinitrotoluene) and ammonium nitrate.

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Formation of diazonium salt

The reaction of aniline with nitrous acid (HNO2) in the presence of strong acid (HCl) at low temperatures produces a diazonium salt.

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Study Notes

Cyanide

  • General Formula: R-CN or R-CEN
  • Functional Group: -CN or -CEN
  • Common Name: Alkyl Cyanide
  • IUPAC Name: Alkane Nitrile
  • Cyanide Nomenclature
  • Alkyl group attached to carbon atom, triple bond with nitrogen.
  • Common names are alkyl cyanide, IUPAC names are alkane nitrile

Cyanide Preparation

  • From Alkyl Halides: R-X + M-CN → R-CN + M-X (M = alkali metal e.g., Na, K, Li)
  • From Acid Amides: RCONHâ‚‚ + Pâ‚‚Oâ‚… → R-CN + HPO₃

Cyanide Properties

  • Mendius Reduction: R-CN + 4[H] → R-CHâ‚‚NHâ‚‚ (Primary amine) or LiAlHâ‚„ used
  • Reaction with Grignard Reagents: R-CN + R-MgX → R-C(O)R' + MgX + NH₃ (In acidic medium producing ketone)

Cyanide Uses

  • Paper, textiles, plastics
  • Killing ants, rat poisons, pesticides
  • Metallurgy for electroplating, metal cleaning, gold removal

Isocyanides

  • General Formula: R-NC
  • Functional Group: -N=C
  • Common Name: Alkyl isocyanide
  • IUPAC Name: Alkane iso-nitrile
  • Isocyanide preparation
  • From alkyl halides: R-X + AgCN -> RNC + AgX
  • From alkyl amine: RNH2 + CH3I + 3KOH -> RNC + 3KI + 3H2O

Isocyanide Properties

  • Stephen Reaction: Isocyanides do not undergo Stephen reaction.
  • Grignard Reagents: Isocyanides do not react with Grignard reagents.
  • Hydrolysis: R-NC + 2Hâ‚‚O (acidic medium) → R-COOH + NH₃
  • Thermal Stability: Less stable alkyl isocyanide on heating are converted into stable alkyl cyanide.
  • Medium Reduction: Alkyl isocyanides with SHSOH/Hâ‚‚ to give secondary amines.

Isocyanide Uses

  • Pesticides, paints, plastics

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Amine Chemistry PDF

Description

Test your knowledge on the reactions and properties of isocyanides and cyanides. This quiz covers key topics such as the Stephen reaction, hydrolysis in acidic medium, and the nomenclature of these compounds. Perfect for students studying organic chemistry concepts.

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