Welcome to Learn Chemistry by Inam Jazbi! 🚀 Here you’ll find exam‑focused model test questions for Class 12 Chemistry, Chapter 6 (Alkyl Halides & Amines). These notes are designed with clear explanations, colourful layouts, and practice MCQs to help you master concepts and score high in your Federal Board exams. 🌈📖
🌟📘 Model Test Questions — XII Chemistry Chapter #6: Alkyl Halides & Amines (Test #8, 2026 Edition) 🔥⚡ 🎯✨ Complete Notes • MCQs • Mechanisms • Federal Board Prep ✨🎯
Q1. How are alkyl halides prepared by the reaction of alcohol with? Give the equations.
➡️(ii) PX₃
➡️(iii) SOCl₂.
Q2. How would you prepare alkyl halide from alkenes and alkanes?
Q3. Draw all the possible isomers of an alkyl halide with composition C₅H₁₁Cl (8 isomers).
Q4. Why the alkyl part of Grignard’s reagent is nucleophilic in nature? OR Give reason of high reactivity of Grignard’s reagent.
Q5. How can you define a nucleophile? Write the names of four nucleophiles with their typical reagents.
Q6. Convert the following:
Q7. How will you obtain the following?
➡️(i) Ethane from methyl magnesium chloride [Alkylation]
Q8. How can you justify the fact that alkyl halides are water insoluble?
Q9. Explain the following by giving scientific reasons:
➡️ Why β-elimination reactions are not possible in methyl halides? (due to lack of β-H )
➡️Why Sɴ₂ reaction is not favourable in tertiary alkyl halides? (due to steric hindrance)
➡️ Why tertiary carbocation is more stable than secondary and primary carbocations?
➡️ E₂ reaction is of 2ᵑᵈ order while that of E₁ is of 1st order. (E₂ is bimolecular and is E₁ unimolecular)
➡️ 2° alkyl halides give Sɴ₁ mechanism in presence of polar solvent. (polar solvents helps in ionization)
➡️Alkyl group behaves as a nucleophile in Grignard’s reagent. (EP Mg makes R nucleophilic)
➡️Why the mechanism of Sɴ₂ reaction completes in one step?
Q10. Why alkyl halide undergoes nucleophilic substitution reaction? Which reagent is required to convert a methyl iodide into:
➡️(i) methanol
➡️(ii) methyl cyanide
➡️(iii) dimethyl ether
➡️(iv) thiol
Q1. Why are secondary and tertiary amines more alkaline than primary amines?
Q2. How is primary amine converted into secondary and tertiary amines, give the equations.
Q3. Give an account on the basicity of amines.
Q4. How are amines prepared from nitriles, give the equations.
Q1. How can you define nucleophilic substitution reactions? Describe the mechanisms of Sɴ₁ and Sɴ₂ reactions. Write down 5 differences between Sɴ₁ and Sɴ₂ .
OR
Outline the step-wise reaction mechanism of the following:
➡️(i). Sɴ₂ reaction between bromomethane and NaOH
➡️(ii) Sɴ₁ reaction between 2-chloro-2-methylpropane and NaCN
Q2. What is β-elimination/ Discus the mechanisms of E₁ and E₂ reactions.
Q3. What are organometallic compounds? What are the key properties of organometallic compounds? How is Grignard’s reagent prospered? Write down the reactions of Grignard’s reagent with water, carbon dioxide, ester and amines.
OR
How do you convert Grignard’s reagent into three types of alcohols? Give only general equations.
Q4. What are Alkyl Halides? How are they classified? Define primary, secondary and tertiary alkyl halides. Give their general structures and examples.
Q5. Draw the orbital structure of methyl iodide and explain the type of hybridization in it.
Q6. Give a comparative study between nucleophilic substitution reactions and elimination reactions of alkyl halides.
Q7. Complete and balance the following reactions:
➡️ R–MgX + CO₂ → R–CO₂MgX → R–CO₂H + MgX₂
➡️ R–OH + SOCl₂ → R–OCl + SO₂ + HCl
➡️ H₃C–MgCl + CO₂ → H₃C–CO₂MgX → H₃C–CO₂H + MgX₂
➡️ H₅C₂–Br + AgNO₂ → H₅C₂–NO₂ + AgB
➡️ R–OH + PCl₅ → R–Cl + POCl₃ + HCl
➡️ H₃C–I + NaCN → H₃C–CN + NaI
➡️ R–MgX + H₃C–NH₂ → R–H + Mg(H₃C–NH)X
➡️ R–MgX + H– OH → R–H + Mg(OH)X
🌈📘 Multiple Choice Questions — Alkyl Halides & Amines (Text Book)
1️⃣ Which of the following composition justifies the secondary alkyl halide?
🟦 (a) R₃CX
🟩 (b) R₂CHX ✅
🟨 (c) RCH₂X
🟥 (d) CH₃X
2️⃣ Which of the following alkyl halide cannot produce an alkene while treated with alcoholic KOH?
🟦 (a) Methyl bromide ✅
🟩 (b) Ethyl bromide
🟨 (c) Propyl bromide
🟥 (d) Butyl bromide
3️⃣ Ethyl magnesium bromide with carbon dioxide yields:
🟦 (a) Methanoic acid
🟩 (b) Ethanoic acid
🟨 (c) Propanoic acid ✅
🟥 (d) Butanoic acid
4️⃣ Grignard’s reagent with ester produces:
🟦 (a) Aldehyde
🟩 (b) Carboxylic acid
🟨 (c) Ketone ✅
🟥 (d) Ether
5️⃣ Amine act as bases because:
🟦 (a) They accept OH⁻
🟩 (b) They donate OH⁻
🟨 (c) They donate H⁺
🟥 (d) They accept H⁺ ✅
6️⃣ The structure of primary amine is:
🟦 (a) Planar trigonal
🟩 (b) Regular tetrahedral
🟨 (c) Tetrahedral pyramidal ✅
🟥 (d) Linear
7️⃣ Alkyl amine reacts with nitrous acid + HCl to yield:
🟦 (a) Diazonium salt ✅
🟩 (b) Aldehyde
🟨 (c) Ketone
🟥 (d) Alcohol
8️⃣ Sɴ₂ reaction occurs most easily if the substrate is:
🟦 (a) Methyl iodide ✅
🟩 (b) Ethyl iodide
🟨 (c) 2‑iodopropane
🟥 (d) 2‑iodobutane
9️⃣ Suitable reagent required for synthesis of propane from methyl magnesium iodide:
🟦 (a) H₂O
🟩 (b) NH₃
🟨 (c) CH₃OH
🟥 (d) CH₃NH₂
⚠️ Note: All given options are wrong. Correct reagent should be C₂H₅Cl ✅
🔟 The rate of Sɴ₁ mechanism depends upon:
🟦 (a) Concentration of substrate only ✅
🟩 (b) Concentration of attacking nucleophile only
🟨 (c) Concentration of both substrate & nucleophile
🟥 (d) Polar solvent
1️⃣1️⃣ The reagent used for converting alcohols into alkyl chlorides is:
🟦 (a) PCl₅
🟩 (b) SOCl₂
🟨 (c) HCl + ZnCl₂
🟥 (d) All of these ✅
1️⃣2️⃣ Ethyl bromide on reaction with alcoholic KOH gives:
🟦 (a) Ethanol
🟩 (b) Ethene ✅
🟨 (c) Ethyl potassium
🟥 (d) Ethyl hydroxide
1️⃣3️⃣ Which of the following alkyl halides reacts fastest in SN1 mechanism?
🟦 (a) Methyl chloride
🟩 (b) Ethyl chloride
🟨 (c) Isopropyl chloride
🟥 (d) tert‑Butyl chloride ✅
1️⃣4️⃣ Which of the following is a leaving group in nucleophilic substitution reactions?
🟦 (a) OH⁻
🟩 (b) Cl⁻ ✅
🟨 (c) NH₂⁻
🟥 (d) CN⁻
1️⃣5️⃣ Which of the following amines does not react with Grignard’s reagent to yield alkane?
🟦 (a) Primary amine
🟩 (b) Secondary amine
🟨 (c) Tertiary amine ✅
🟥 (d) Ammonia
1️⃣6️⃣ Reaction of alkyl halide with aqueous KOH gives:
🟦 (a) Alcohol ✅
🟩 (b) Alkene
🟨 (c) Ether
🟥 (d) Amine
1️⃣7️⃣ Which of the following is formed when methyl magnesium iodide reacts with carbon dioxide followed by hydrolysis?
🟦 (a) Methanoic acid
🟩 (b) Ethanoic acid ✅
🟨 (c) Propanoic acid
🟥 (d) Butanoic acid
1️⃣8️⃣ Which of the following alkyl halides will undergo Sɴ₂ reaction most rapidly?
🟦 (a) Methyl iodide ✅
🟩 (b) Ethyl iodide
🟨 (c) Isopropyl iodide
🟥 (d) tert‑Butyl iodide
1️⃣9️⃣ Which of the following reagents is used for the identification of alkyl halides in the laboratory?
🟦 (a) Ammoniacal silver nitrate ✅
🟩 (b) Silver oxide
🟨 (c) Silver nitrite
🟥 (d) Silver sulphate
2️⃣0️⃣ Which of the following statements is correct about Sɴ₁ reactions?
🟦 (a) They proceed via carbocation intermediate
🟩 (b) They are unimolecular in rate‑determining step
🟨 (c) They show racemization of products
🟥 (d) All of these ✅
2️⃣1️⃣ Which of the following would not yield alkane on reaction with Grignard’s reagent?
🟦 (a) Ammonia
🟩 (b) Primary amine
🟨 (c) Secondary amine
🟥 (d) Tertiary amine ✅
2️⃣2️⃣ Grignard’s reagent gives primary alcohol on reaction with:
🟦 (a) Methanal ✅
🟩 (b) Ethanal
🟨 (c) Acetone
🟥 (d) CO₂
2️⃣3️⃣ Grignard’s reagent adds to the carbon‑oxygen double bond of carbonyl compounds to form an addition product called:
🟦 (a) Magnesium halide alkoxides ✅
🟩 (b) Secondary alcohol
🟨 (c) Primary alcohol
🟥 (d) Tertiary alcohol
2️⃣4️⃣ Which one of the following is NOT used for identification of alkyl halide in the laboratory?
🟦 (a) Ammoniacal silver nitrate
🟩 (b) Silver oxide
🟨 (c) Silver nitrite
🟥 (d) Silver sulphate ✅
2️⃣5️⃣ Which of the following will produce alcohol by the action of alkyl halide on?
🟦 (a) Alcoholic caustic potash
🟩 (b) Aqueous ammonia
🟨 (c) Aqueous caustic potash ✅
🟥 (d) Water
2️⃣6️⃣ Sɴ₂ reactions complete in _______ steps.
🟦 (a) 1 ✅
🟩 (b) 2
🟨 (c) 3
🟥 (d) 4
2️⃣7️⃣ Sɴ₁ reactions complete in _______ steps.
🟦 (a) 1
🟩 (b) 2 ✅
🟨 (c) 3
🟥 (d) 4
2️⃣8️⃣ Which of the following undergo Sɴ₁ reactions?
🟦 (a) (CH₃)₂CH–Cl
🟩 (b) CH₃Cl
🟨 (c) (CH₃)₃C–Cl ✅
🟥 (d) All of them
2️⃣9️⃣ The composition of sodium‑lead alloy is:
🟦 (a) Na₄Pb ✅
🟩 (b) Na₂Pb
🟨 (c) Na–Pb
🟥 (d) NaPb₂
3️⃣0️⃣ A primary alkyl halide would prefer to undergo _____________.
🟦 (a) Sɴ₁ reaction
🟩 (b) SN₂ reaction ✅
🟨 (c) α‑Elimination
🟥 (d) Racemization
3️⃣1️⃣ Which of the following alkyl halides will undergo Sɴ₁ reaction most readily?
🟦 (a) (CH₃)₃C—F
🟩 (b) (CH₃)₃C—Cl
🟨 (c) (CH₃)₃C—Br
🟥 (d) (CH₃)₃C—I ✅
3️⃣2️⃣ Tertiary alkyl halides are practically inert to substitution by Sɴ₂ mechanism because of:
🟦 (a) Insolubility
🟩 (b) Instability
🟨 (c) Inductive effect
🟥 (d) Steric hindrance ✅
3️⃣3️⃣ For which mechanisms, the first step involved is the same:
3️⃣4️⃣ The alcohol‑free and moisture‑free organic solvent used in the preparation of Grignard’s reagent is called:
🟦 (a) Dry acid
🟩 (b) Dry ether
🟨 (c) Dry anhydrous ether
🟥 (d) Both b and c ✅
3️⃣5️⃣ Which of the following reactions are favoured by polar aprotic solvent?
🟩 (b) Sɴ₂ reactions ✅
🟨 (c) Sɴ₁ reactions
🟥 (d) None of them
3️⃣6️⃣ Which one of the following does not form Grignard’s reagent?
🟦 (a) CH₃Cl
🟩 (b) CH₃Br
🟨 (c) CH₃I
🟥 (d) CH₃F ✅
3️⃣7️⃣ Which C–X bond has the highest bond energy per mole?
🟦 (a) C–F ✅
🟩 (b) C–Br
🟨 (c) C–Cl
🟥 (d) C–I
2️⃣8️⃣ Neo‑pentyl bromide refers to follow which mechanism during substitution reactions?
🟦 (a) Not show Sɴ reactions
🟩 (b) Sɴ₂✅
🟨 (c) Sɴ₁
🟥 (d) Both a and c
3️⃣9️⃣ If a nucleophile is the attacking reagent, which one would be the most reactive?
🟦 (a) R–F
🟩 (b) R–Cl
🟨 (c) R–Br
🟥 (d) R–I ✅
4️⃣0️⃣ CH₃–Cl can show which of the following reactions with easiness?
🟦 (a) Sɴ₂ ✅
🟩 (b) Sɴ₁
🟨 (c) E₂
🟥 (d) Both a and b
4️⃣1️⃣ Neutral nucleophiles among the following is:
🟦 (a) CN⁻
🟩 (b) NH₃ ✅
🟨 (c) Cl⁻
🟥 (d) C₂H₅O⁻
4️⃣2️⃣ 100% inversion of configuration takes place during:
🟩 (b) Sɴ₂ ✅
🟨 (c) E₁
🟥 (d) E₂
4️⃣3️⃣ During Sɴ₂ mechanism carbon atom changes its state of hybridization as:
🟦 (a) sp → sp²
🟩 (b) sp² → sp³
🟨 (c) sp³ → sp
🟥 (d) sp³ → sp² ✅
🌈📘✨ Answers of XII Chemistry Model Test Questions ✨📘🌈 🔥⚡ Chapter # 6 — Alkyl Halides and Amines ⚡🔥 ✍️🔹 Short Questions of Alkyl Halides 🔹✍️
Q1. How are alkyl halides prepared by the reaction of alcohol with?
(i) HX (ii) PX₃ (iii) SOCl₂. Give the equations.
Answer
Alkyl halides are prepared by the action of halogen acid on the alcohol in the presence of anhydrous zinc chloride as a catalyst.
✨ Order of reactivity of different halogen acids
HI> HBr> HI
✨ Order of reactivity of Different Types of alcohols
tertiary alcohol > secondary alcohol > primary alcohol.
✨Lucas reagent
Least reactive acid (HCl) reacts with least reactive alcohol (primary) only in the presence of catalyst ZnCl₂.
The mixture of concentrated HCl and ZnCl₂ is called Lucas reagent.
✨Rate of Different Types of Alcohols and Lucas Test
Three types of alcohols undergo the reaction with Lucas reagent at different rates. Thus this reaction is used to distinguish between primary, secondary and tertiary alcohols. This test is called Lucas Test.
➡️a) With tert-alcohols, insoluble layer/cloudy ppt of alkyl halide is formed immediately with Lucas reagent.
➡️ b) With sec-alcohols, turbidity alkyl halide is formed within few (5-10) minutes.
➡️c) With primary alcohols, no immediate reaction (alkyl halide is only formed on heating).
🔥💥Preparation of Alkyl Halide By By the action of Halogenated agents (Phosphorus Halides or Thionyl Chloride) on alcohols
The reactions of alcohols with halogenated agents like phosphorus halides (such as PCl₃, PBr₃, Pl₃, PCl₅, PBr₅) and thionyl chloride or sulphur dichloride oxide (SOCl₂) in the presence of pyridine base as a catalyst (Pyridine is used to absorb HCl) give corresponding alkyl halides. The –OH group alcohols can be replaced by a halogen atom by the reaction of alcohols with halogenated agents like halogen acids or with reagents like PCl₃, PCl₅ or SOCl₂ (thionyl chloride). The thionyl chloride method is preferred for the preparation of alkyl halides because both the products are in gaseous state.
Q2. How would you prepare alkyl halide from alkenes and alkanes?
Answer
Preparation of Alkyl halide By the Photochemical Halogenation of Alkane
Alkanes are halogenated in sunlight or at high temperature giving alkyl halides. This reaction involves the substitution of one or more hydrogen atoms of alkanes by halogen atoms resulting in the formation of a mixture of different halogenated alkanes (haloalkanes). In addition to monohalides (monohaloalkanes) dihalides, trihalides and higher halides are also produced and their separation is not easy, so this is not a good method for the preparation of alkyl halides.
Preparation of Alkyl halide By the Hydrohalogenation of Alkene
Alkenes add a molecule of hydrohalic acid (HX) yielding respective alkyl halides. Markownikoff’s rule is operated in addition of HX to unsymmetrical alkenes. Order of reactivity of different halogen acids is HI> HBr > HCl.
Q3. Draw all the possible isomers of an alkyl halide with composition C₅H₁₁Cl (8 isomers).
Answer
Q4. Why the alkyl part of Grignard’s reagent is nucleophilic in nature? OR Give reason of high reactivity of Grignard’s reagent.
Answer
Nature and Reason of Reactivity of Grignard’s Reagent
Grignard’s reagent are much reactive than most of the organic compounds. The C–Mg bond in Grignard’s Reagent is covalent but highly polar due to high electronegativity of carbon atom and electrophilic nature of Mg metal. The formation of Grignard’s reagent changes the nature of alkyl group from electrophilic to Nucleophilic as halogen is more electronegative making magnesium electrophilic and carbon of alkyl group Nucleophilic. Stated differently, due to electrophilic (electropositive) nature of Mg metal the C–Mg covalent bond in Grignard’s reagent is highly polar giving a partial positive charge on Mg atom and partial negative charge on alkyl carbon. This alkyl group is electron-rich and acts as a nucleophile (carbanion). i.e. the carbon of alkyl group of Grignard’s Reagent behaves as a nucleophile (carbanion). This negative charge on alkyl group is an unusual character making the alkyl groups highly reactive toward electrophilic centres.
Due to nucleophilic nature of alkyl parts, Grignard’s reagent reacts with polarized molecules either by nucleophilic substitution or nucleophilic addition. Thus characteristic reactions of Grignard’s reagent will give Nucleophilic substitution (SN) and Nucleophilic addition (AN) reactions. Mostly reactions shown by Grignard’s reagent are exothermic.
Q5. How can you define a nucleophile? Write the names of four nucleophiles with their typical reagents.
Answer
✨Nucleophiles
Nucleophile is a chemical specie within the attacking molecule that can donate a pair of electrons to form a covalent bond (in fact coordinate covalent bond) with electrophilic atom of other molecules.
✨Some Common Strong Nucleophiles along with their Typical Reagents
Q6. Convert the following:
(a) Methyl magnesium bromide into acetone
(b) Ethyl chloride into ethyl amine
(c) Ethyl chloride into ethyl alcohol
(d) Ethyl amine into imine
Answer
🔥(a) Nucleophilic Carbonyl Addition in of methyl magnesium bromide into ester; ethyl acetate yielding Halo magnesium dialkoxide as adduct followed by its acidification into ketone, acetone
🔥(c) SN of Cl group of ethyl chloride by –OH group of aqueous KOH giving ethyl alcohol
🔥(d) Reactions of primary amine with Aldehydes and Ketones giving Imines (Schiff Bases)
Q7. How will you obtain the following?
(i) Ethane from methyl magnesium chloride [Alkylation]
(ii) Ethanoic acid from methyl magnesium chloride [Carbonation]
(iii) tertiarybutyl alcohol from ketone [Nucleophilic carbonyl addition of GR]
(iv) Ethyl alcohol from methyl magnesium iodide [Nucleophilic carbonyl addition of GR]
(v) secondary alcohol from Grignard’s reagent [Nucleophilic carbonyl addition of GR]
Answer
(i) Ethane from Methyl Magnesium chloride through its methylation with methyl chloride
(ii) Ethanoic acid from methyl magnesium chloride By its carbonation or Nucleophilic Carbonyl Addition of CO₂ into Halo magnesium carboxylate as adduct followed by its acidification
(iii) tertiary-butyl alcohol from ketone (acetone) by its Nucleophilic Carbonyl Addition in Methyl magnesium chloride into Halo magnesium alkoxide as adduct followed by its acidification
(iv) Ethyl alcohol from methyl magnesium iodide by its Nucleophilic Carbonyl Addition in formaldehyde into Halo magnesium alkoxide as adduct followed by its acidification
(v) secondary alcohol from Grignard’s reagent by its Nucleophilic Carbonyl Addition in higher aldehydes into Halo magnesium alkoxide as adduct followed by its acidification
Q8. How can you justify the fact that alkyl halides are water insoluble?
Answer
Alkyl halides in spite of their polar nature polar (dipole moment 2.05 to 2.15 D) are slightly soluble or almost insoluble in water due to their inability to form hydrogen bonds with water molecules and also their inability to break hydrogen bond between water molecules.
Details
To be miscible with water, the solute-water force of attraction must be stronger than the solute-solute and water-water forces of attraction. Both alkyl halides and water are polar molecules. Alkyl halides are polar molecules and so held together by relatively weak dipole-dipole interactions while strong intermolecular H-bonds exist between the water molecules. When alkyl halides are mixed with water a new force of attraction between the alkyl halides and water comes into play, this new force of attraction is much weaker than the forces of attractions already existing between two alkyl halides and two water molecules respectively. This is the reason that alkyl halides, though polar, are immiscible with water.
Q9. Explain the following by giving scientific reasons:
▶ Why β-elimination reactions are not possible in methyl halides? (due to lack of β-H )
▶ Why Sɴ₂ reaction is not favourable in tertiary alkyl halides? (due to steric hindrance)
▶ Why tertiary carbocation is more stable than secondary and primary carbocations?
▶Alkyl group behaves as a nucleophile in Grignard’s reagent. (EP Mg makes R nucleophilic)
▶ Why the mechanism of Sɴ₂ reaction completes in one step?
Answer
▶ Why β-elimination reactions are not possible in methyl halides? (due to lack of β-H )
b-elimination reactions or 1,2-elimination reactions are the type of elimination reaction involving the removal of b-hydrogen and electronegative functional groups (such as X¯ or OH¯) from two adjacent carbon atoms of the substrate like alkyl halides by the attack of alcoholic alkali like KOH giving a product with multiple bond (unsaturated compound). Hence for b-elimination reactions to proceed, there should be at least one β-hydrogen in the molecule. Since methyl halides lack b-hydrogen, therefore, they cannot undergo b-elimination reactions.
▶ Why Sɴ₂ reaction is not favourable in tertiary alkyl halides? (due to steric hindrance)
Tertiary alkyl halides readily undergo Sɴ₁ reaction because their carbonium ions (R₃C⁺) are most stable due the stabilizing effect of electron-donating alkyl groups that favours the formation of carbocation intermediate thereby facilitating the Sɴ₁ reaction. In addition, greatest steric hindrance in tertiary alkyl halides hinders the backside nucleophilic attack thereby preventing Sɴ₂ reaction.
Sɴ₂ reactions take place in primary alkyl halides (RCH₂X) or methyl halides (CH₃X) because primary carbocation or carbonium ions (R–CH₂⁺) and methyl carbocation (CH₃⁺) are highly unstable due to the lack of electron donating alkyl groups. In addition, least steric hindrance in primary alkyl halides favours the backside nucleophilic attack.
▶ Why tertiary carbocation is more stable than secondary and primary carbocations?
The tertiary carbocation or carbonium ions (R₃C⁺) are most stable due the stabilizing effect of three electron-donating alkyl groups. An increased inductive effect (+I effect) by three methyl groups stabilizes the positive charge on the carbocation.
In E₂, reaction rate is proportional to the concentrations of both the eliminating agent (base) and the substrate i.e. primary alkyl halide. Thus it exhibits second-order kinetics. In E₁, the reaction rate is proportional to the concentration of the substrate i.e. tertiary alkyl halide. Thus it exhibits first-order kinetics.
Alternate Wordings
the rate of E₂ reaction depends on the concentration of both the substrate (primary alkyl halide) and the base making it a 2nd order reaction and also a bimolecular reaction with molecularity of two.
The rate of E₁ reaction depends only on the concentration of the substrate (tertiary alkyl halide) and it is independent of the concentration of attacking base making it a 1st order reaction and also a unimolecular reaction with molecularity of one.
A secondary alkyl halide may undergo Sɴ reaction either through Sɴ₁ or Sɴ₂ mechanism (due to the fact Many secondary carbocations are stable, so it may undergo Sɴ₁ reaction but Sɴ₂ reaction is also favourable because of very less steric hindrance).
The key factor used to predict the reaction mechanism either Sɴ₁ or Sɴ₂ reaction is The nature of the solvent, in which the reaction is taking place.’ Most of the substitution reactions take place in polar solvents; Polar solvents can be further divided into Polar protic solvents and Polar aprotic solvents.
Sɴ₁ reactions always take place in polar protic solvents like water, whereas Sɴ₂ reactions always take place in polar aprotic solvents. In the case of Sɴ₁ reactions, polar protic solvents speed up the rate of Sɴ₁ reactions because the polar solvent stabilize the carbocation intermediate.
▶ Alkyl group behaves as a nucleophile in Grignard’s reagent. (EP Mg makes R nucleophilic)
Due to greater electrophilic (electropositive) nature of Mg metal the C–Mg covalent bond in Grignard’s reagent is highly polar giving a partial positive charge on Mg atom and partial negative charge on alkyl carbon. This alkyl group is electron-rich and acts as a nucleophile (carbanion). i.e. the carbon of alkyl group of Grignard’s Reagent behaves as a nucleophile or carbanion. Carbanions are excellent nucleophiles. The formation of Grignard’s reagent changes the nature of alkyl group from electrophilic to Nucleophilic as halogen is more electronegative making magnesium electrophilic and carbon of alkyl group Nucleophilic. This negative charge on alkyl group is an unusual character making the alkyl groups highly reactive toward electrophilic centres.
▶ Why the mechanism of Sɴ₂ reaction completes in one step?
The Sɴ₂ reaction is a concerted reaction that completes in one step. The SN2 reaction is a nucleophilic substitution reaction where a bond is broken and another is formed synchronously. The Sɴ₂ mechanism is a one-step process in which a nucleophile attacks the substrate, and a leaving group departs simultaneously. The substrate and the nucleophile are both present in the transition state for this step. Because two molecules are present in the transition state, the reaction is bimolecular. Two reacting species are involved in the rate determining step of the reaction, so the reaction is of 2nd order.
Q10. Why alkyl halide undergoes nucleophilic substitution reaction? Which reagent is required to convert a methyl iodide into:
(i) methanol (ii) methyl cyanide (iii) dimethyl ether (iv) thiol
Answer
The reactivity of alkyl halide is due to the polarity of C–X bond. Since the halogen atom is more electronegative than carbon atom, therefore carbon atom attached to halogen atom carries a partial positive charge i.e. it becomes electrophilic in nature while halogen atom develops a partial negative charge i.e. it becomes nucleophilic in nature. The electrophilic a-carbon atom of alkyl halide has a tendency to undergo nucleophilic substitution reaction by accepting an electron pair from a nucleophilic reagent and forms a new carbon-nucleophile bond while in doing so old C–X bond breaks giving X– ion. It involves heterolytic cleavage.
Suitable reagent for the Conversion of methyl iodide into Required Product
Short Questions of Amines
Q1. Why are secondary and tertiary amines more alkaline than primary amines?
Answer
The basicity of amines is affected by the number and nature of alkyl or aryl groups attached to the nitrogen atom. Electron donating groups like –CH₃, –OCH₃, –NH₂ increase basicity while electron-withdrawing groups like –NO₂, –CN, –X (halogens) decrease the basicity of amine. Since secondary and tertiary amines contain two and three alkyl groups respectively which make them more alkaline than alkaline amines.
Alkyl groups are electron-releasing groups and thus they donate electrons to the more electronegative nitrogen. The greater the number of alkyl groups, greater is the inductive effect which makes the electron density on the alkylamine's nitrogen greater. The small amount of extra negative charge built up on the nitrogen atom makes the lone pair even more attractive towards hydrogen ions. Correspondingly, primary, secondary, and tertiary alkyl amines are more basic than ammonia. Similarly, secondary and tertiary amines are more basic than primary amines due to the presence of two and three alkyl groups respectively.
Q2. How is primary amine converted into secondary and tertiary amines, give the equations.
Answer
Conversion of primary amine into secondary and tertiary amine by Alkylation using Alkyl halides
Primary amines react with alkyl halides adding an alkyl group to form secondary and tertiary amines. In this reaction, hydrogen atoms of amines are replaced by alkyl groups.
Q3. Give an account on the basicity of amines.
Answer
All classes of amines are basic in nature giving alkaline solution. The basicity of amines is attributed to the non-bonding lone pair of electrons on nitrogen atom which can be donated easily making them Lewis bases. This non-bonding electron pair is shared with proton of acids making them Bronsted-Lowry bases giving rise to basic characteristic of amines.
The basicity of amines is affected by the number and nature of alkyl or aryl groups attached to the nitrogen atom.
▶ All aliphatic amines are more basic than ammonia.
▶ All aromatic amines are weaker bases than ammonia.
▶ Electron donating groups like –CH₃, –OCH₃, –NH₂ increase basicity while electron-withdrawing groups like –NO₂, –CN, –X (halogens) decrease the basicity of amine.
Aliphatic amines are more basic than aromatic amines. Like aromatic amines, the lone pair of electrons present on nitrogen participates in resonance and is therefore not available for donation, whereas it is available in aliphatic amines.
Q4. How are amines prepared from nitriles, give the equations.
Answer
Preparation of Amines from nitriles by its Reduction by nascent H Using LiAlH₄ or by H₂ using Rh-Al₂O₃, Pt or Raney nickel
Chemical or Catalytic Reduction of alkyl or aryl nitriles with nascent hydrogen in the presence of LiAlH₄ or with hydrogen gas in the presence of with Rh-Al₂O₃, Pt or Raney nickel gives primary amines with one carbon more than the parent nitriles. This reaction produces amines with one more carbon atom than the original nitriles ascending in the amine series.
Descriptive Questions
Q1. How can you define nucleophilic substitution reactions? Describe the mechanisms of Sɴ₁ and Sɴ₂ reactions. Write down 5 differences between Sɴ₁ and Sɴ₂.
OR
Outline the step-wise reaction mechanism of the following:
Answer
Definition of Nucleophilic Substitution Reactions or SN reactions
The substitution reactions in which a strong nucleophile (electron deficient species) displaces the weaker nucleophile (–X) from electrophilic carbon of the substrate (compound) are called Nucleophilic Substitution Reactions or SN reactions [where S stands for substitution and N for nucleophilic]. These reactions occur in alkyl halides. There are two types of SN Reactions
➡️ Sɴ₂ or Bimoleuclar Nucleophilic Substitution Reactions (Single-step Reaction)
➡️ Sɴ₁ or Unimolecular Nucleophilic Substitution Reactions (Two-steps Reaction)
General Representation
Some Common Strong Nucleophiles along with their Typical Reagents and Class of Product
Nu⁻ = OH⁻, SH⁻, OR⁻, SR⁻, CN⁻, NH₂⁻,–NHR, >NR₂, –NR₃, RCOO⁻, NO₂⁻, etc.
Mechanism of Sɴ₂ Reactions
Sɴ₂ reaction is a bimolecular single-step Sɴ reaction in which formation of the carbon-nucleophile bond and the cleavage of carbon-halogen bond occur simultaneously. In other words attacking nucleophile (Nu¯) becomes partially attached to the electrophilic carbon of alkyl halide as well as the halogen (X¯) atom is detached at the same time. This state is called Transition State. In Sɴ₂ reaction, the attacking nucleophile always comes from the back side because the front side is sterically hindered by the nucleophile of the substrate.
As the bond making and bond breaking processes occur simultaneously, it is also the “Rate determining or slow step” i.e. it determines the overall rate of the reaction. Since two molecules undergo change in covalency in the rate determining step of reaction, therefore one step nucleophilic substitution reaction is bimolecular reaction and is symbolized as Sɴ₂ which stands for Bimolecular Nucleophilic Substitution Reaction.
Mechanism of Sɴ₁ Reactions
In this two steps reaction, the first step is the rate determining step comprises of slow reversible ionization of C–X bond into R+ (carbonium ion) and X¯ (halide) ions and in second step Carbonium ion reacts with attacking nucleophile (Nu¯) to form the final product.
It is unimolecular bi-step Sɴ reaction. The Sɴ₁ reaction mechanism proceed in two distinct steps, with the first step involving the departure of the leaving group (the halide group) from the substrate molecule, leading to the formation of a carbocation intermediate, followed by nucleophilic attack in the second step leading to formation of substituted product.
ORQ1. Outline the step-wise reaction mechanism of the following:
(i) Sɴ₂ reaction between bromomethane and NaOH
(ii) Sɴ₁ reaction between 2-chloro-2-methylpropane and NaCN
Answer
(i) Sɴ₂ reaction between bromomethane and NaOH
(ii) Sɴ₁ reaction between 2-chloro-2-methylpropane and NaCN
Q2. What is β-elimination/ Discus the mechanisms of E₁ and E₂ reactions.
Answer
Definition of β-Elimination Reaction
The type of elimination reaction involving the removal of b-hydrogen and electronegative functional groups (such as X¯ or OH¯) from two adjacent carbon atoms of the substrate like alkyl halides by the attack of alcoholic alkali like KOH giving a product with multiple bond (unsaturated compound) is called 1,2-eleimination or b-elimination reactions.
Examples
1. Dehydrohalogenation of alkyl halide with a base.
2. Acid catalysed dehydration of alcohols.
Types of Elimination Reaction (By Hughes and Ingold; 1941)
1. Bimolecular b-elimination reaction (E₂ reaction).
2. Unimolecular b-elimination reaction (E₁ reaction).
Mechanism of E₂ reactions
In E₂ reactions, the removal of outgoing nucleophilic halide (X¯) group and removal of β-hydrogen by the attack of strong base (e.g. OH¯) take place simultaneously through transition state in which attacking nucleophile becomes partially attached to electrophilic-acidic β-hydrogen of substrate as well as the halide group (X¯) is detached at the same time. This momentary unstable high-energy state is termed as transition state which readily changes to alkene by removing b-hydrogen and halide group.
As the base (like OH¯) attacks or removes the b-hydrogen from b-carbon with simultaneous separation of halogen atom from a-carbon as halide (X¯) ion and formation of double bond, take place in the single step which is also the rate-determining step in which two molecules take part, therefore, it is a bimolecular reaction. The net result is the loss of HX from alkyl halide called dehydrohalogenation which is known as β-elimination reaction. Thus one step elimination reaction involving two molecules in rate-determining step is termed as bimolecular β-elimination reaction designated as E₂.
Mechanism of E₁ reaction
The mechanism of E₁ reaction involves two steps. the first step involves the ionization of substrate tertiary alkyl halides into carbocation intermediate with the departure of halogen atoms from the substrate which is the slow and rate-determining step. The second step involves the attack of a base on β-hydrogen removing a proton from the β-carbon (the carbon next to the halogenated carbon), leading to the formation of a double between the two adjacent carbon atoms.
Q3. What are organometallic compounds? What are the key properties of organometallic compounds? How is Grignard’s reagent prepared? Write down the reactions of Grignard’s reagent with water, carbon dioxide, ester and amines.
Answer
Definition of Organometallic Compounds
Organometallic compounds are defined as the organic compounds that contains at least one bond between carbon atom and a metal atom.
Examples of Common Organometallic Compounds
1. Grignard’s reagent; a highly reactive organic compound used in organic synthesis.
2. Dimethyl zinc; used as insecticide
3. Tetraethyl lead; used as knock inhibitor in petroleum industry
4. Methylcobalamine; a derivative of vitamin B-12
5. Haemoglobin and Chlorophyll (Society, Technology and Science)
Key Properties of Organometallic Compounds
State: Exist in liquid & mainly in solid form, especially with aromatic or ring-structured Hydrocarbon groups
Solubility: insoluble in water and soluble in organic solvents such as ether.
Metal-Carbon Bond: This bond is highly covalent.
Reactivity: Extremely reactive in nature and hence stored in organic solvents only.
Electronegativity: most metals forming organometallic compounds have electronegativity is less than 2.
Reducers: Organometallic compounds produced by electropositive metals act as reducing agents
Spontaneous Combustion: Organometallic compounds of Li and Na are extremely volatile in nature
Toxicity: volatile Organometallic compounds have been reported to be toxic to humans.
Preparation of Grignard’s Reagent
Grignard’s reagent or alkyl magnesium halide is a well-known organometallic compound that contains a carbon-magnesium (C–Mg) bond formulated as R–Mg–X [Where; R = alkyl or aryl group, X = Cl, Br or I]
Grignard’s reagent is prepared in the laboratory by the action of an alkyl halide on magnesium turning in the presence of dry anhydrous ether (which is pure anhydrous diethyl ether; C₂H₅OC₂H₅).
Factors Controlling Ease of Formation of Grignard’s reagent
1. Size of alkyl groups
The ease of formation of Grignard’s reagent depends upon the size of the alkyl group. The larger the size of the alkyl group, the more difficult is the formation of Grignard’s reagent.
2. Nature of halogen atoms
The nature of halogen affects the ease of formation of Grignard’s reagent. The order is I> Br > Cl because the bond between iodine and carbon is weaker than corresponding bond with other halogens.
Reactions of Grignard’s Reagent with water
When Grignard’s Reagent reacts with water in an acidic medium, it yields alkanes.
Reactions of Grignard’s Reagent with primary amine
Grignard’s reagent reacts with primary amine to produce an alkane.
Reactions of Grignard’s Reagent with CO₂
Grignard’s reagent react with solid CO₂ as nucleophilic addition reaction to the electrophilic carbon of CO₂ across carbon-oxygen double bond to yield an intermediate addition product; magnesium salts of carboxylic acid (halo magnesium carboxylate) which on hydrolysis in acidic medium (or acidification) with an aqueous acid give next higher carboxylic acids containing one carbon atom more than Grignard’s reagent. The reaction is known as Carboxylation or Carbonation of Grignard’s reagent.
Reactions of Grignard’s Reagent with Ester
Grignard’s reagent reacts with ester first forming unstable addition product which is later on stabilized with the formation of ketone through rearrangement.
OR
How do you convert Grignard’s reagent into three types of alcohols? Give only general equations.
Answer
Grignard’s reagent react with formaldehyde, higher aldehydes like acetaldehyde and ketones like acetone to give primary, secondary and tertiary alcohols respectively.
Grignard’s reagent reacts with all solid carbonyl compounds (i.e. formaldehyde, higher aldehydes and ketones) as a nucleophilic addition reaction to the electrophilic carbon of carbonyl group across carbon-oxygen double bond of carbonyl compounds to give an intermediate addition product; magnesium salts of alcohols (magnesium halide alkoxide) which on hydrolysis (or acidification) with aqueous halogen acid (HX) forming next higher primary, secondary and tertiary alcohols containing one carbon atom more than Grignard’s reagent respectively. The alcohols obtained by this method contain more carbon than carbonyl compounds.
Q4. What are Alkyl Halides? How are they classified? Define primary, secondary and tertiary alkyl halides. Give their general structures and examples.
Answer
Definition
Alkyl halides also called halogenoalkanes or monohaloalkanes or simply Haloalkanes are monohalogen derivative of alkanes derived by the replacement of one hydrogen atom in an aliphatic hydrocarbon or alkanes by one halogen atom (chlorine, bromine or iodine). We can also say that alkyl halides are a subset of the general class of halocarbons. Generally, alkyl halides contain halogen atoms attached to the sp³ hybridized carbon atom of alkyl groups. e.g. CH₃Cl, C₂H₅Br, C₃H₇I etc.
The term halogen generally excludes fluorine as fluorocarbon compounds and their reactions differ markedly from other halocarbon chemistry.
General and Type Formula
Alkyl halides form the homologous series having general formula CₙH₂ₙ₊₁–X with type formula R–X where R stands for alkyl groups and X represents Cl, Br or I.
Classification of Alkyl Halides
Alkyl halides are classified as primary, secondary and tertiary depending upon whether the halide (–X) group is attached to primary, secondary or tertiary carbon atom respectively.
A primary (1°) alkyl halides is characterized by halogen-bearing carbon being attached to only one other carbon atom. A secondary (2°) alkyl halide refers to an alkyl halide where the halogen-bearing carbon is linked to two carbon atoms. A tertiary (3°) alkyl halide has the structure in which halogen-bearing carbon is further bonded to three carbon atoms.
Q5. Draw the orbital structure of methyl iodide and explain the type of hybridization in it.
Answer
In alkyl halides, carbon atom is sp³-hybridized as each carbon is bonded to four other atoms. In the first homologue of alkyl halide known as methyl chloride (CH₃Cl), carbon atom is sp³-hybridized as predicted by hybrid orbital theory. Since carbon of methyl chloride is bonded to four atoms signifying that carbon is utilizing its all four valence electrons to produce four sp³ hybrid orbitals orientating at an angle of 109° to give a tetrahedral geometry. These four sp³ hybrid orbitals shared with three s-orbitals of hydrogen atoms and one p-orbital of chlorine by head on overlapping to make four sigma bonds acquiring tetrahedral shape.
Q6. Give a comparative study between nucleophilic substitution reactions and elimination reactions of alkyl halides.
Answer
Nucleophilic substitution reactions can occur alongside the elimination reactions because the nucleophile can also act as a base. It is easily seen that when substrate R–X will be treated with an electron pair donor species (e.g. Base or Nucleophilic reagents), there will be always two products. e.g.:
However, Nucleophilic substitution reactions takes place when the nucleophile attacks on the a-carbon atom whereas elimination reactions occur when the nucleophile attacks on the β-hydrogen.
When the attacking nucleophile (Y⁻) is a strong base (e.g. OH⁻, RO⁻) the dominant reaction is E₂ and Sɴ₂ reaction will be a side reaction. However when the attacking nucleophile (Y⁻) is highly polarizing and weakly basic (e.g. I⁻, Br⁻, CH₃COO⁻) then main reaction will be Sɴ₂ and E₂ will be a side reaction. e.g.
Factors
Several factors can influence the formation of products via either substitution or elimination mechanisms:
Solvent Effect
Substitution reactions are favoured in polar solvent while elimination reactions are favours in non-polar solvents.
Base Effect
A strong base promotes elimination reactions and hinders substitution reactions.
Temperature Effect
The rise in temperature encourages elimination reaction over substitution reactions
Substrate Effect
If the substrate molecule is a tertiary alkyl halides, it favours elimination reaction while if it is a primary alkyl halide, it favours substitution reaction. Secondary alky halide is consented to both substitution & elimination.
Conclusion
High temperature, more crowded structure of alkyl halide (tertiary) and more concentration of attacking group also favours E₂ reaction while low temperature, less crowded structure of alkyl halide (primary) and less concentration of attacking group favours Sɴ₂ reaction. [Presence of solvent also favours E₂ reaction e.g. the dehydrohalogenation of alkyl halide (E₂ reaction) takes place in the presence of alcohol].
Q7. Complete and balance the following reactions:
Answer
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😔 یہ مجھے چین کیوں نہیں پڑتا
🧑🤝🧑 ایک ہی شخص تھا جہان میں کیا
🧑🤝🧑 ایک ہی شخص تھا جہان میں کیا
🌹 کتنی دل کش ہو تم کتنا دلجو ہوں میں
⚰️ کیا ستم ہے کہ ہم لوگ مر جائیں گے
⚰️ کیا ستم ہے کہ ہم لوگ مر جائیں گے
🏚️ کون اس گھر کی دیکھ بھال کرے
🪞 روز اک چیز ٹوٹ جاتی ہے
🪞 روز اک چیز ٹوٹ جاتی ہے
🤲 بہت نزدیک آتی جا رہی ہو
💔 بچھڑنے کا ارادہ کر لیا کیا
💔 بچھڑنے کا ارادہ کر لیا کیا
🤷♂️ کیسے کہیں کہ تجھ کو بھی ہم سے ہے واسطہ کوئی
🤐 تو نے تو ہم سے آج تک کوئی گلہ نہیں کیا
🤐 تو نے تو ہم سے آج تک کوئی گلہ نہیں کیا
💞 کیا کہا عشق جاودانی ہے!
🕰️ آخری بار مل رہی ہو کیا
🕰️ آخری بار مل رہی ہو کیا
🪨 علاج یہ ہے کہ مجبور کر دیا جاؤں
🙉 وگرنہ یوں تو کسی کی نہیں سنی میں نے
🙉 وگرنہ یوں تو کسی کی نہیں سنی میں نے
🏘️ اس گلی نے یہ سن کے صبر کیا
🚶♂️ جانے والے یہاں کے تھے ہی نہیں
🚶♂️ جانے والے یہاں کے تھے ہی نہیں
🌍 حاصل کن ہے یہ جہان خراب
⏳ یہی ممکن تھا اتنی عجلت میں
⏳ یہی ممکن تھا اتنی عجلت میں
🔗 اب جو رشتوں میں بندھا ہوں تو کھلا ہے مجھ پر
🕊️ کب پرند اڑ نہیں پاتے ہیں پروں کے ہوتے
🕊️ کب پرند اڑ نہیں پاتے ہیں پروں کے ہوتے
🔥 جونؔ ایلیا کے اشعار 🔥
🏠 آج بہت دن بعد میں اپنے کمرے تک آ نکلا تھا
🌸 جوں ہی دروازہ کھولا ہے اس کی خوشبو آئی ہے
🌸 جوں ہی دروازہ کھولا ہے اس کی خوشبو آئی ہے
⚔️ یہ وار کر گیا ہے پہلو سے کون مجھ پر
🔄 تھا میں ہی دائیں بائیں اور میں ہی درمیاں تھا
🔄 تھا میں ہی دائیں بائیں اور میں ہی درمیاں تھا
🌫️ ساری گلی سنسان پڑی تھی باد فنا کے پہرے میں
👤 ہجر کے دالان اور آنگن میں بس اک سایہ زندہ تھا
👤 ہجر کے دالان اور آنگن میں بس اک سایہ زندہ تھا
🔄 اک عجب آمد و شد ہے کہ نہ ماضی ہے نہ حال
📜 جونؔ برپا کئی نسلوں کا سفر ہے مجھ میں
📜 جونؔ برپا کئی نسلوں کا سفر ہے مجھ میں
🏰 حملہ ہے چار سو در و دیوار شہر کا
🌳 سب جنگلوں کو شہر کے اندر سمیٹ لو
🌳 سب جنگلوں کو شہر کے اندر سمیٹ لو
🏠 پہلے رہتے تھے کوچئہ دل میں
💔 اب پتا کیا ہے دل فگاروں کا جونؔ
💔 اب پتا کیا ہے دل فگاروں کا جونؔ
⚠️ کیا کہوں جان کو بچانے میں
☠️ جونؔ خطرہ ہے جان جانے کا
🔥 یہ جہاں جونؔ! اک جہنم ہے
🚫 یاں خدا بھے نہیں ہے آنے کا
⏳ زندگی ایک فن ہے لمحوں کا
🎭 اپنے انداز سے گنوانے کا
☠️ جونؔ خطرہ ہے جان جانے کا
🔥 یہ جہاں جونؔ! اک جہنم ہے
🚫 یاں خدا بھے نہیں ہے آنے کا
⏳ زندگی ایک فن ہے لمحوں کا
🎭 اپنے انداز سے گنوانے کا
🌙 آج کے بعد عشرتِ مجلسِ شامِ غم کہاں
💔 دل نہ لگے گا تیرے بعد پر تیرے بعد ہم کہاں
🌸 نکہتِ یاسمین قبا بھول نہ جائیو ہمیں
🌅 صبح کے بعد تُو کہاں شام کے بعد ہم کہاں
😶 یہ جو نواگری کے ساتھ چیخ نہیں رہا ہوں میں
🫀 سینہ نے نواز میں آخر اب اتنا دم کہاں
👁️ اب یہ جبین و چشم و لب تجھ کو نظر نہ آئیں گے
🔍 غور سے دیکھ لے ہمیں آج کے بعد ہم کہاں
💔 دل نہ لگے گا تیرے بعد پر تیرے بعد ہم کہاں
🌸 نکہتِ یاسمین قبا بھول نہ جائیو ہمیں
🌅 صبح کے بعد تُو کہاں شام کے بعد ہم کہاں
😶 یہ جو نواگری کے ساتھ چیخ نہیں رہا ہوں میں
🫀 سینہ نے نواز میں آخر اب اتنا دم کہاں
👁️ اب یہ جبین و چشم و لب تجھ کو نظر نہ آئیں گے
🔍 غور سے دیکھ لے ہمیں آج کے بعد ہم کہاں
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