JEE FOUNDATION - CARBON AND ITS COMPOUNDS

Advanced Question Bank (Excluding Chemical Properties)

Prepared for: JEE Foundation students
Date: August 12, 2025

SUMMARY - KEY CONCEPTS

SUMMARY - KEY CONCEPTS (brief) 1. Carbon: atomic number 6, electronic configuration 1s2 2s2
2p2, tetravalent, catenation, multiple bonding. 2. Allotropes: Diamond (sp3 tetrahedral
network), Graphite (sp2 layered with delocalized pi-electrons), Fullerene (spherical C60),
Amorphous forms: coal, charcoal, lampblack. 3. Hydrocarbons: Alkanes (CnH2n+2), Alkenes
(CnH2n), Alkynes (CnH2n-2). Saturated = single bonds only. Unsaturated = double/triple bonds.
4. Functional groups: -OH (alcohol), -CHO (aldehyde), -CO (ketone), -COOH (carboxylic acid), -X
(halide), -NH2 (amine). 5. Isomerism: structural (chain, position, functional) and
stereoisomerism (not covered in depth here). 6. IUPAC basics: longest chain, principal
functional group, numbering for substituents, suffixes -ane/-ene/-yne, alkyl substituent
naming.

ADVANCED QUESTION BANK

SECTION A - ADVANCED MCQs (choose the best option; some require multi-step thinking)
A1. Compound X has empirical formula CH2 and vapour density 28. The compound is an alkene. What
is its molecular formula? a) C2H4 b) C3H6 c) C4H8 d) C5H10
A2. Which of the following statements about graphite and diamond is FALSE? a) Diamond is an
electrical insulator; graphite conducts electricity. b) Both diamond and graphite are
allotropes of carbon. c) Diamond has sp2 hybridisation; graphite has sp3 hybridisation.
d) Graphite shows lubricating properties due to weak interlayer forces.
A3. Identify the compound that shows functional isomerism with propanal (CH3CH2CHO). a)
Propan-2-ol b) Propanone (acetone) c) 1-Propanol d) Prop-1-ene
A4. A compound gives a positive Tollens' test and has formula C3H6O. Which pair of structures
is possible? a) CH3CH2CHO and CH3COCH3 b) CH3CH(OH)CH3 and CH3CH2CHO c) CH3COCH3
and CH3CH2OH d) CH3CH2CHO and CH2=CHCH2OH
A5. Consider C4H6 isomer A which is linear with one triple bond, and isomer B which is cyclic.
Which of the following is/are correct? a) Both can exist, A is but-1-yne or but-2-yne; B
can be cyclobutene. b) Only linear forms possible, no cyclic isomers. c) C4H6 cannot
form cyclic compounds. d) Linear with triple bond and cyclic are same structure.
A6. Which of the following has the highest degree of unsaturation? a) C6H12 b) C6H10 c)
C6H8 d) C6H6
A7. The IUPAC name of CH3-CH(CH3)-CH2-CH3 is: a) 2-Methylbutane b) 3-Methylbutane c)
2,2-Dimethylpropane d) 2-Butylpropane
A8. Which pair of compounds are structural isomers (same molecular formula) but belong to
different homologous series? a) C2H6 and C2H4 b) C3H6O (propanone and propanal) -
yes/no style c) C3H8 and C3H6 d) C4H10 and C4H10 (two structural isomers of butane
family)
A9. A hydrocarbon has 85.7% carbon by mass and the rest hydrogen. The molar mass is
approximately 56 g/mol. Identify the molecular formula. a) C4H8 b) C3H8 c) C2H4 d)
C5H12
A10. Compound with formula C5H8 could be: a) An alkyne (one triple bond) with linear chain
b) A cycloalkene pair c) A diene d) Any of the above (requires reasoning on degrees of
unsaturation)
SECTION B - ASSERTION & REASON (choose: A - both true & R true & R explains A; B - both true R
false; C - A true R false; D - A false R true)
B1. Assertion (A): Fullerene (C60) is aromatic. Reason (R): It has conjugated pi-electron
system over the cage leading to delocalization. B2. A: Graphite conducts electricity due to
delocalized pi-electrons. R: Each carbon in graphite is sp2 hybridized leaving one p-orbital
electron delocalized over the plane. B3. A: Methane shows isomerism. R: Methane can form chain
isomers with same formula. B4. A: In homologous series, physical properties change gradually.
R: Members differ by -CH2- unit which changes molecular mass and intermolecular forces.
SECTION C - NUMERICAL / CALCULATION BASED
C1. A compound contains 80% carbon by mass and 20% hydrogen. Its molar mass is 42 g/mol.
Determine its empirical and molecular formula. Show steps. C2. A gaseous hydrocarbon has
density 1.75 g/L at STP (1 atm, 273 K). If molar mass of gas equals density × 22.4, find the
likely formula among: C2H4, C3H6, C4H8, C3H8. Explain reasoning. C3. The combustion of 0.5 g of
a hydrocarbon yields 1.1 g CO2 and 0.45 g H2O. Determine empirical formula of the hydrocarbon.
C4. A compound with formula CxHyO gives a positive Tollen's test; product mass of CO2 on
combustion of 0.2 g sample is 0.44 g. Determine x and y if atom counts are small (<=6).
SECTION D - MULTI-STEP STRUCTURAL REASONING
D1. A compound A reacts with Br2 in CCl4 slowly and with KMnO4 vigorously to give a diacid. A
decolorizes HBr in presence of peroxide but does not undergo addition of H2 in catalytic
hydrogenation. Propose possible structure(s) for A and justify. D2. Two isomers have formula
C4H8O. One gives Tollens' test and boils at 48 degreesC, the other does not and has a higher Rf
in TLC. Identify likely functional groups and draw structures. Give IUPAC names. D3. Predict
all isomers (constitutional) for C5H10 that are alkenes. Classify them into straight-chain and
branched, and indicate which show geometric (cis/trans) isomerism.
SECTION E - ISOMERISM CHALLENGE SET (DRAW & EXPLAIN)
E1. Draw all structural isomers for C4H8. Indicate which are cycloalkanes, which are alkenes;
for alkenes, show cis/trans if applicable. E2. For formula C3H6O, draw all isomers (functional
+ positional) and classify them: aldehydes, ketones, alcohols, ethers (if any), and enols
(tautomeric forms where applicable). Indicate which are interconvertible by tautomerism. E3. A
compound with formula C6H12 exhibits 4 degrees of structural isomerism as alkenes. List and
draw all isomers that are possible (constitutional only).
SECTION F - STRUCTURE / DIAGRAM BASED (NAME & PROPERTIES)
F1. Name the following structural fragment and predict one physical property (boiling point
trend) for each: (a) CH3-CH2-CH2-OH (b) CH3-CH2-O-CH3 (c) CH3-CH2-COOH F2. Given a skeletal
structure (user will be shown), deduce if it will be optically active. Explain what structural
features cause chirality.
SECTION G - MIXED CONCEPT PROBLEMS (INTEGRATION)
G1. Explain why diamond is an insulator while graphite is a conductor, using bonding and band
theory basics. Give one example of a property of each allotrope that follows from structure.
G2. A polymeric chain has repeating unit -CH2-CH2-O- (polyethylene oxide). Propose a method of
naming and deduce monomer unit. Discuss if carbon catenation plays role in polymer stability.
G3. Suggest a retrosynthetic pathway to obtain 2-methylpropan-1-ol from propene using reagents
and brief reaction steps (focus on functional group changes; chemical properties excluded from
exam scope here).
SECTION H - EXAM STYLE FULL QUESTIONS (2 marks - 8 marks) H1 (2 marks). Draw the structure of
2-methylpropene and label all types of carbon (primary, secondary, tertiary). H2 (3 marks).
Give IUPAC names for: (a) CH3-CH(CH3)-CH2-CH2-OH (b) CH3-CO-CH2-CH3 H3 (5 marks). A 0.2 g
sample of a compound yields 0.88 g CO2 and 0.36 g H2O on complete combustion. Calculate
empirical formula and suggest a molecular formula if molar mass ~ 86 g/mol. H4 (8 marks).
Complete organic synthesis problem: Starting from 1-butene, design a 3-step sequence to obtain
2-butanol (regioselectively). Indicate reagents and brief mechanism notes.
SECTION I - ANSWER KEYS & HINTS (short guidance) - For numerical Qs, show stepwise atom-mass
conversions; empirical formula from percent composition. - For isomer counts, use degree of
unsaturation: DU = C - H/2 + N/2 +1 (for hydrocarbons ignore heteroatoms) - IUPAC naming:
longest chain and lowest set of locants for substituents. - For assertion-reason, test each
statement independently then test explanatory power.