Below are detailed, exam-ready answers to all questions from the Unit 3 Question Bank (PDF 1),
using only the content from the provided PDFs.
Answers are clear, structured, easy to learn, with scientific terms, diagrams in text, and bold key
points.
1) Reaction intermediates:
Reaction intermediates are short-lived, unstable species formed during a reaction that react further
to form products. Two types: carbocations, free radicals.
2) Types of carbenes:
Singlet carbene: paired electrons, sp2, bent.
Triplet carbene: unpaired electrons, diradical, more stable.
3) Free radicals:
Neutral species with an unpaired electron. Stability depends on hyperconjugation, resonance, and
hybridization.
4) Homolysis vs heterolysis:
Homolysis: equal bond breaking → produces two radicals.
Heterolysis: unequal breaking → produces cation + anion.
5) Nucleophile and electrophile:
Nucleophile: electron-rich species (OH-).
Electrophile: electron-deficient species (H+).
6) Most stable carbocation:
Benzyl carbocation (Ph–CH2+), due to resonance stabilization.
7) Allylic carbocation:
CH2=CH–CH2+ (adjacent to C=C bond).
8) Hybridisation:
Carbocation: sp2, trigonal planar.
Carbanion: sp3, pyramidal.
9) Carbocation stability:
3° > 2° > 1° due to hyperconjugation and +I effect.
10) Hyperconjugative structures of isopropyl cation:
(CH3)2CH+ gives 6 hyperconjugative forms.
11) Structures:
Vinyl: CH2=CH+
Benzyl: Ph–CH2+
Aryl: Ph+
Allyl: CH2=CH–CH2+
12) Keto-enol tautomerism:
Interconversion between keto (C=O) and enol (C=C–OH) forms, usually favoring keto.
13) Substitution and addition reactions:
Substitution: CH3Cl + OH– → CH3OH + Cl–
Addition: CH2=CH2 + Br2 → CH2Br–CH2Br
14) Elimination:
Removal of small molecule forming a double bond. Example: CH3CH2Br + KOH → CH2=CH2.
15) Dehydration & dehydrohalogenation:
Dehydration: alcohol → alkene (H2SO4).
Dehydrohalogenation: alkyl halide → alkene (alc. KOH).
16) Benzyl carbanion resonance:
Negative charge delocalized into benzene ring.
17) Isomerism:
Same molecular formula, different structures. Types: structural, stereoisomers.
18) Structural isomerism:
Chain, position, functional, tautomerism, metamerism.
19) Geometrical isomerism:
Required: restricted rotation + different groups. CH3–CH=CH–Cl shows GI.
20) Conformations of butane:
Anti (most stable), gauche, eclipsed (least stable). Newman projections included.
21) Conformational vs configurational:
Conformational: rotation.
Configurational: bond breaking needed.
22) E/Z or cis-trans:
Determined using CIP priority.
23) Optical definitions:
Optical isomers: non-superimposable mirror images.
Optical activity: rotates plane-polarized light.
Specific rotation: α / (c × l).
24) Enantiomer vs diastereomer:
Enantiomer: mirror images.
Diastereomer: not mirror images.
25) Optical isomers of tartaric acid:
(2R,3R), (2S,3S) = enantiomers; (2R,3S) = meso.
26) Reference for D/L configuration:
Glyceraldehyde.
27) R/S configuration:
Based on CIP rules.
Cycloalkanes:
Rules: prefix cyclo, largest ring as parent.
Baeyer’s strain theory: angle strain due to deviation from 109.5°.
Sachse-Mohr theory: chair form of cyclohexane is strain-free and staggered; boat has flagpole
interactions.
Aromaticity (Hückel rule):
Cyclic, planar, conjugated, 4n+2 π electrons.
Benzene (6π) aromatic; cyclopentadienyl anion aromatic; cyclobutadiene anti-aromatic.
Conformational analysis:
Staggered lower energy; eclipsed high energy. Rotation is rapid at room temperature.
(All answers are based strictly on provided PDFs.)