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843 things you should know to secure top 100 Rank in IIT -JEE

Physical & General Chemistry

General Chemistry Done
1 Apply the law of the conservation of mass. 
2 Compare and contrast the three common states of matter: solid, liquid, and gas.
Describe the classifications of matter: elements, compounds, and mixtures
3 (heterogeneous and homogeneous).
Understand the difference between chemical changes (chemical reactions) and physical
4 changes.
5 Distinguish between chemical properties and physical properties.
6 Become familiar with the SI (metric) system of units, including the SI prefixes.
7 Convert from one temperature scale to another. 
8 Calculate the density of a substance. 
9 Use density to relate mass and volume.
10 Apply dimensional analysis to solving numerical problems.
11 Convert from one metric unit to another metric unit. 
12 Convert from one metric volume to another metric volume. 
13 Convert from any unit to another unit. 
Atoms, Molecules, and Ions
14 Describe Thomson’s experiment in which he discovered the electron.
15 Describe Rutherford’s experiment that led to the nuclear model of the atom.
16 Write the nuclide symbol for a given nuclide.
17 Define and provide examples of isotopes  of an element.
18 Write the nuclide symbol of an element. 
Determine the atomic mass of an element from the isotopic masses and fractional
19 abundances. 
20 Determine when the chemical formula  of a compound represents a molecule.
21 Determine whether a chemical formula is also a molecular formula.
22 Define ion, cation,  and anion.
23 Classify compounds as ionic  or molecular.
24 Define and provide examples for the term formula unit.
25 Specify the charge on all substances, ionic and molecular.
26 Write an ionic formula, given the ions. 
27 Learn the rules for predicting the charges of monatomic ions  in ionic compounds.
28 Apply the rules for naming monatomic ions.
29 Learn the names and charges of common polyatomic ions.
30 Name an ionic compound from its formula.
31 Write the formula of an ionic compound from its name. 
32 Determine the order of elements in a binary (molecular) compound.
Learn the rules for naming binary molecular compounds, including the Greek prefixes.
33
34 Name a binary compound from its formula. 
35 Write the formula of a binary compound from its name. 
36 Name a binary molecular compound from its molecular model. 
37 Recognize molecular compounds that are acids.
38 Determine whether an acid is an oxoacid.
39 Learn the approach for naming binary acids and oxoacids.
40 Write the name and formula of an anion from the acid. 
41 Recognize compounds that are hydrates.
42 Learn the rules for naming hydrates.
43 Name a hydrate from its formula. 
44 Write the formula of a hydrate from its name. 

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Write chemical equations using appropriate phase labels, symbols of reaction

45 conditions, and the presence of a catalyst.
46 Determine if a chemical reaction is balanced.
47 Master the techniques for balancing chemical equations. 
Calculations with Chemical Formulas and Equations
48 Calculate the formula mass from a formula. 
49 Calculate the formula mass from molecular models. 
50 Define the quantity called the mole.
51 Learn Avogadro’s number.
52 Understand how the molar mass  is related to the formula mass of a substance.
53 Calculate the mass of atoms and molecules. 
54 Perform calculations using the mole.
55 Convert from moles of substance to grams of substance. 
56 Convert from grams of substance to moles of substance.
57 Calculate the number of molecules in a given mass of substance.
58 Define mass percentage.
59 Calculate the percentage composition of the elements in a compound. 
60 Calculate the mass of an element in a given mass of compound. 
61 Describe how C, H, and O combustion analysis is performed.
62 Calculate the percentage of C, H, and O from combustion data. 
63 Define empirical formula.
Determine the empirical formula of a binary compound from the masses of its
64 elements. 
65 Determine the empirical formula from the percentage composition. 
Understand the relationship between the molecular mass of a substance and its
66 empirical formula mass.
Determine the molecular formula from the percentage composition and molecular
67 mass. 
Relate the coefficients in a balanced chemical equation to the number of molecules or
68 moles (molar interpretation ).
69 Use the coefficients in a chemical reaction to perform calculations.
70 Relate the quantities of reactant to the quantity of product. 
71 Relate the quantities of two reactants or two products. 
Understand how a limiting reactant  or limiting reagent  determines the moles of
product formed during a chemical reaction and how much excess reactant  remains.
72
73 Calculate with a limiting reactant involving moles.
74 Calculate with a limiting reactant involving masses. 
75 Define and calculate the theoretical yield  of chemical reactions.
76 Determine the percentage yield  of a chemical reaction.
From the molecular equation of both strong electrolytes and weak electrolytes,
77 determine the complete ionic equation.
78 From the complete ionic equation, write the net ionic equation.
79 Write net ionic equations. 
80 Recognize precipitation  (exchange ) reactions.
Write molecular, complete ionic, and net ionic equations for precipitation reactions.
81
82 Decide whether a precipitation reaction will occur. 
83 Determine the product of a precipitation reaction.
Understand how an acid–base  indicator is used to determine whether a solution is
84 acidic or basic.
85 Define Arrhenius acid  and Arrhenius base.
86 Write the chemical equation of an Arrhenius base in aqueous solution.
87 Define Brønsted –Lowry acid  and Brønsted –Lowry base.
88 Write the chemical equation of a Brønsted–Lowry base in aqueous solution.

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Write the chemical equation of an acid in aqueous solution using a hydronium ion.
89
90 Learn the common strong acids  and strong bases.
91 Distinguish between a strong acid and a weak acid  and the solutions they form.

Distinguish between a strong base and a weak base  and the solutions they form.
92
93 Classify acids and bases as strong or weak. 
94 Recognize neutralization reactions.
95 Write an equation for a neutralization reaction. 
96 Write the reactions for a polyprotic acid  in aqueous solution.
97 Recognize acid–base reactions that lead to gas formation.
98 Write an equation for a reaction with gas formation. 
99 Define oxidation –reduction  reaction.
100 Learn the oxidation-number rules.
101 Assign oxidation numbers. 
102 Write the half-reactions  of an oxidation–reduction reaction.
103 Determine the species undergoing oxidation  and reduction.
Recognize combination reactions, decomposition reactions, displacement
104 reactions,  and combustion reactions.
105 Use the activity series to predict when displacement reactions will occur.
106 Balance simple oxidation–reduction reactions by the half-reaction method. 
107 Define molarity or molar concentration of a solution.
108 Calculate the molarity from mass and volume. 
109 Use molarity as a conversion factor. 
110 Describe what happens to the concentration of a solution when it is diluted.
111 Perform calculations associated with dilution.
112 Diluting a solution. 
113 Determine the amount of a species by gravimetric analysis. 
114 Calculate the volume of reactant solution needed to perform a reaction. 
115 Understand how to perform a titration .
116 Calculate the quantity of substance in a titrated solution. 
The Gaseous State
117 Define pressure  and its units.
118 Convert units of pressure. 
119 Express Boyle’s law  in words and as an equation.
120 Use Boyle’s law. 
121 Express Charles’s law  in words and as an equation.
122 Use Charles’s law. 
123 Express the combined gas law  as an equation.
124 Use the combined gas law. 
125 State Avogadro’s law.
126 Define standard temperature and pressure  (STP ).
127 State what makes a gas an ideal gas.
128 Learn the ideal gas law  equation.
129 Derive the empirical gas laws from the ideal gas law. 
130 Use the ideal gas law. 
131 Calculate gas density.
132 Determine the molecular mass of a vapor. 
133 Use an equation to calculate gas density.
134 Solving stoichiometry problems involving gas volumes. 
135 Learn the equation for Dalton’s law of partial pressures.
136 Define the mole fraction of a gas.
137 Calculate the partial pressure and mole fractions of a gas in a mixture. 
Describe how gases are collected over water and how to determine the vapor pressure
138 of water.
139 Calculate the amount of gas collected over water. 

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140 List the five postulates of the kinetic theory.

141 Provide a qualitative description of the gas laws based on the kinetic theory.
Describe how the root-mean-square (rms) molecular speed  of gas molecules varies with
142 temperature.

Describe the molecular-speed distribution of gas molecules at different temperatures.

143
144 Calculate the rms speed of gas molecules. 
145 Define effusion  and diffusion.
146 Describe how individual gas molecules move undergoing diffusion.
147 Calculate the ratio of effusion rates of gases. 
148 Explain how and why a real gas  is different from an ideal gas.
149 Use the van der Waals equation. 
Quantum Theory of the Atom
150 Define the wavelength  and frequency  of a wave.
151 Relate the wavelength, frequency, and speed of light. 
152 Describe the different regions of the electromagnetic spectrum.
153 State Planck’s quantization of vibrational energy.
154 Define Planck’s constant  and photon.
155 Describe the photoelectric effect.
156 Calculate the energy of a photon from its frequency or wavelength. 
157 State the postulates of Bohr’s theory of the hydrogen atom.
158 Relate the energy of a photon to the associated energy levels of an atom.
159 Determine the wavelength or frequency of a hydrogen atom transition. 
160 Describe the difference between emission  and absorption  of light by an atom.
161 State the de Broglie relation.
162 Calculate the wavelength of a moving particle. 
163 Define quantum mechanics.
164 State Heisenberg’s uncertainty principle.
Relate the wave function for an electron to the probability of finding it at a location in
165 space.
166 Define atomic orbital.
167 Define each of the quantum numbers for an atomic orbital.
168 State the rules for the allowed values for each quantum number.
169 Apply the rules for quantum numbers. 
170 Describe the shapes of s, p, and d orbitals.
Electron Configurations and Periodicity
171 Define electron configuration and orbital diagram.
172 State the Pauli exclusion principle.
173 Apply the Pauli exclusion principle. 
174 Define building-up principle.
175 Define noble-gas core, pseudo-noble-gas core, and valence electron.
176 Define main-group element and (d-block and f-block) transition element.
177 Determine the configuration of an atom using the building-up principle. 
178 Determine the configuration of an atom using the period and group numbers.
179 State Hund’s rule.
180 Apply Hund’s rule.
181 Define paramagnetic substance  and diamagnetic substance.
182 Describe how Mendeleev predicted the properties of undiscovered elements.
183 State the periodic law.
184 State the general periodic trends in size of atomic radii.
185 Define effective nuclear charge.
186 Determine relative atomic sizes from periodic trends. 
187 State the general periodic trends in ionization energy.
188 Define first ionization energy.
189 Determine relative ionization energies from periodic trends. 
190 Define electron affinity.

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191 State the broad general trend in electron affinity across any period.
192 Define basic oxide, acidic oxide, and amphoteric oxide.
State the main group corresponding to an alkali metal, an alkaline earth metal, a
193 chalcogen, a halogen, and a noble gas.
Describe the change in metallic/nonmetallic character (or reactivities) in going through
194 any main group of elements.
Ionic and Covalent Bonding
195 Define ionic bond.
196 Explain the Lewis electron-dot symbol of an atom.
197 Use Lewis symbols to represent ionic bond formation. 
198 Describe the energetics of ionic bonding.
199 Define lattice energy.
Describe the Born–Haber cycle to obtain a lattice energy from thermodynamic data.
200
201 Describe some general properties of ionic substances.
202 State the three categories of monatomic ions of the main-group elements.
203 Write the electron configuration and Lewis symbol for a main-group ion. 
204 Note the polyatomic ions given earlier in Table 2.5.
205 Note the formation of 2+ and 3+ transition-metal ions.
206 Write electron configurations of transition-metal ions. 
207 Define ionic radius.
208 Define isoelectronic ions.
209 Use periodic trends to obtain relative ionic radii.
210 Describe the formation of a covalent bond between two atoms.
211 Define Lewis electron-dot formula.
212 Define bonding pair  and lone (nonbonding) pair  of electrons.
213 Define coordinate covalent bond.
214 State the octet rule.
215 Define single bond, double bond,  and triple bond.
216 Define polar covalent bond.
217 Define electronegativity.
218 State the general periodic trends in the electronegativity.
219 Use electronegativity to obtain relative bond polarity. 
220 Write Lewis formulas with single bonds only. 
221 Write Lewis formulas having multiple bonds. 
222 Write Lewis formulas for ionic species. 
223 Define delocalized bonding.
224 Define resonance description.
225 Write resonance formulas. 
226 Write Lewis formulas (exceptions to the octet rule). 
227 Note exceptions to the octet rule in Group IIA and Group IIIA elements.
228 Define formal charge.
229 State the rules for obtaining formal charge.
230 State two rules useful in writing Lewis formulas.
231 Use formal charges to determine the best Lewis formula. 
232 Define bond length (bond distance).
233 Define covalent radii.
234 Define bond order.
235 Explain how bond order and bond length are related. 
236 Define bond energy.
237 Estimate ∆H from bond energies. 
Molecular Geometry and Chemical Bonding Theory
The Valence-Shell Electron-Pair Repulsion (VSEPR) Model
238 Define molecular geometry.
239 Define valence-shell electron-pair repulsion model.

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Note the difference between the arrangement of electron pairs about a central atom
240 and molecular geometry.
241 Note the four steps in the prediction of geometry by the VSEPR model.
242 Predict the molecular geometry (two, three, or four electron pairs). 
Note that a lone pair tends to require more space than a corresponding bonding pair
243 and that a multiple bond requires more space than a single bond.
244 Predict the molecular geometry (five or six electron pairs). 
245 Define dipole moment.
246 Explain the relationship between dipole moment and molecular geometry. 
Note that the polarity of a molecule can affect certain properties, such as a boiling
247 point.
Valence Bond Theory
248 Define valence bond theory.

State the two conditions needed for bond formation, according to valence bond theory.
249
250 Define hybrid orbitals.
251 State the five steps in describing bonding, following the valence bond theory.
252 Apply valence bond theory (two, three, or four electron pairs). 
253 Apply valence bond theory (five or six electron pairs).
254 Define σ (sigma ) bond.
255 Define A ( pi ) bond.
256 Apply valence bond theory (multiple bonding). 
Explain geometric, or cis–trans,  isomers in terms of the p-bond description of a double
257 bond.
258 Define molecular orbital theory.
259 Define bonding orbitals and antibonding orbitals.
260 Define bond order.
State the two factors that determine the strength of interaction between two atomic
261 orbitals.
262 Describe the electron configurations of H 2, He2, Li2, and Be2.
263 Define homonuclear diatomic molecules and heteronuclear diatomic molecules.
264 Describe molecular orbital configurations (homonuclear diatomic molecules). 
265 Describe molecular orbital configurations (heteronuclear diatomic molecules). 
266 Describe the delocalized bonding in molecules such as O 3.
States of Matter; Liquids and Solids
Compare a gas, a liquid, and a solid using a kineticmolecular theory description.
267
268 Define change of state (phase transition).
269 Define melting, freezing, vaporization, sublimation, and condensation.
270 Define vapor pressure.
Describe the process of reaching a dynamic equilibrium that involves the vaporization
271 of a liquid and condensation of its vapor.
272 Define boiling point.
273 Describe the process of boiling.
274 Define freezing point and melting point.
275 Define heat (enthalpy) of fusion and heat (enthalpy) of vaporization.
276 Calculate the heat required for a phase change of a given mass of substance. 
Describe the general dependence of the vapor pressure (ln P ) on the temperature (T ).
277
278 Calculate the vapor pressure at a given temperature. 
279 Calculate the heat of vaporization from vapor pressure. 
280 Define phase diagram.
Describe the melting-point curve and the vapor-pressure curves (for the liquid and the
281 solid) in a phase diagram.
282 Define triple point.
283 Define critical temperature and critical pressure.

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284 Relate the conditions for the liquefaction of a gas to its critical temperature. 
285 Define intermolecular forces.
286 Define dipole–dipole force.
287 Describe the alignment of polar molecules in a substance.
288 Define London (dispersion) forces.
289 Note that London forces tend to increase with molecular mass.
290 Relate the properties of liquids to the intermolecular forces involved.
291 Define hydrogen bonding.
292 Identify the intermolecular forces in a substance. 
293 Determine relative vapor pressures on the basis of intermolecular attractions.
294 Define molecular solid, metallic solid, ionic solid, and covalent network solid.
295 Identify types of solids. 
296 Relate the melting point of a solid to its structure.
297 Determine relative melting points based on types of solids. 
298 Relate the hardness and electrical conductivity of a solid to its structure.
299 Define crystalline solid and amorphous solid.
300 Define crystal lattice and unit cell of a crystal lattice.
Define simple cubic unit cell, body-centered cubic unit cell, and face-centered cubic
301 unit cell.
302 Determine the number of atoms in a unit cell. 
303 Describe the two kinds of crystal defects.
304 Define hexagonal close-packed structure and cubic close-packed structure.
305 Define coordination number.
Note the common structures (face-centered cubic and body-centered cubic) of metallic
306 solids.
307 Describe the three types of cubic structures of ionic solids.
308 Describe the covalent network structure of diamond and graphite.
309 Calculate atomic mass from unit-cell dimension and density. 
310 Calculate unit-cell dimension from unit-cell type and density. 
Solutions and Surface Chemistry
311 Define solute and solvent.
312 Define miscible fluid.
313 Provide examples of gaseous solutions, liquid solutions, and solid solutions.
List the conditions that must be present to have a saturated solution,  to have
314 an unsaturated solution,  and to have asupersaturated solution.
315 Describe the factors that make one substance soluble in another.
316 Determine when a molecular solution  will form when substances are mixed.
317 Learn what conditions must be met in order to create an ionic solution.
318 State the general trends of the solubility of gases and solids with temperature.
319 Explain how the solubility of a gas changes with temperature.
320 Apply Henry’s law. 
321 Define colligative property.
322 Define molarity.
323 Define mass percentage of solute.
324 Calculate with mass percentage of solute.
325 Define molality.
326 Calculate the molality of solute. 
327 Define mole fraction.
328 Calculate the mole fraction of components. 
329 Convert molality to mole fractions. 
330 Convert mole fractions to molality. 
331 Convert molality to molarity. 
332 Convert molarity to molality. 
333 Explain vapor-pressure lowering of a solvent.
334 State Raoult’s law.
335 Calculate vapor-pressure lowering.

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336 Describe an ideal solution.

337 Define boiling-point elevation and freezing-point depression.
338 Calculate boiling-point elevation and freezing-point depression. 
339 Calculate the molecular mass of a solute from molality. 
340 Calculate the molecular mass from freezing-point depression. 
341 Describe a system where osmosis  will take place.
342 Calculate osmotic pressure. 
343 Determine the colligative properties of ionic solutions. 
344 Define colloid.
345 Explain the Tyndall effect.
346 Give examples of hydrophilic colloids and hydrophobic colloids.
347 Describe coagulation.
348 Explain how micelles can form an association colloid.
Rates of Reaction
349 Define reaction rate.
350 Explain instantaneous rate and average rate of a reaction.
351 Explain how the different ways of expressing reaction rates are related. 
352 Calculate average reaction rate. 
353 Describe how reaction rates may be experimentally determined.
354 Define and provide examples of a rate law , rate constant,  and reaction order.
355 Determine the order of reaction from the rate law. 
356 Determine the rate law from initial rates. 
Learn the integrated rate laws for first-order, second-order, and zero-order reactions.
357
358 Use an integrated rate law. 
359 Define half-life of a reaction.

Learn the half-life equations for first-order, second-order, and zero-order reactions.
360
361 Relate the half-life of a reaction to the rate constant. 
362 Plot kinetic data to determine the order of a reaction.
363 State the postulates of collision theory.
364 Explain activation energy  (E a ).
Describe how temperature, activation energy, and molecular orientation influence
365 reaction rates.
366 State the transition-state theory.
367 Define activated complex.
Describe and interpret potential-energy curves  for endothermic and exothermic
368 reactions.
369 Use the Arrhenius equation. 
370 Define elementary reaction, reaction mechanism, and reaction intermediate.
371 Write the overall chemical equation from a mechanism. 
372 Define molecularity.
373 Give examples of unimolecular, bimolecular, and termolecular reactions.
374 Determine the molecularity of an elementary reaction. 
375 Write the rate equation for an elementary reaction.
376 Explain the rate-determining  step of a mechanism.
377 Determine the rate law from a mechanism with an initial slow step. 
378 Determine the rate law from a mechanism with an initial fast, equilibrium step. 
379 Describe how a catalyst  influences the rate of a reaction.
380 Indicate how a catalyst changes the potential-energy curve of a reaction.
381 Define homogeneous catalysis  and heterogeneous catalysis.
Chemical Equilibrium
382 Define dynamic equilibrium  and chemical equilibrium.
383 Apply stoichiometry to an equilibrium mixture. 
384 Define equilibrium-constant expression and equilibrium constant.
385 State the law of mass action.

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386 Write equilibrium-constant expressions. 

387 Describe the kinetics argument for the approach to chemical equilibrium.
388 Obtain an equilibrium constant from reaction composition.
389 Describe the equilibrium constant K p ; indicate how K p  and K c  are related.
Obtain K c  for a reaction that can be written as a sum of other reactions of
390 known K c  values.
391 Define homogeneous equilibrium and heterogeneous equilibrium.
392 Write K c  for a reaction with pure solids or liquids. 
393 Give a qualitative interpretation of the equilibrium constant based on its value.
394 Define reaction quotient, Q.
395 Describe the direction of reaction after comparing Q with K c .
396 Use the reaction quotient. 
397 Obtain one equilibrium concentration given the others. 
398 Solve an equilibrium problem (involving a linear equation in x ). 
399 Solve an equilibrium problem (involving a quadratic equation in x ).
400 State Le Châtelier’s principle.

State what happens to an equilibrium when a reactant or product is added or removed.

401
402 Apply Le Châtelier’s principle when a concentration is altered. 
403 Describe the effect of a pressure change on chemical equilibrium.
404 Apply Le Châtelier’s principle when the pressure is altered. 
405 Describe the effect of a temperature change on chemical equilibrium.
406 Apply Le Châtelier’s principle when the temperature is altered. 
407 Describe how the optimum conditions for a reaction are chosen.
408 Define catalyst.
409 Compare the effect of a catalyst on rate of reaction with its effect on equilibrium.
410 Describe how a catalyst can affect the product formed.
Acids and Bases
411 Define acid  and base  according to the Arrhenius concept.
412 Define acid  and base  according to the Brønsted–Lowry concept.
413 Define the term conjugate acid–base pair.
414 Identify acid and base species. 
415 Define amphiprotic species.
416 Define Lewis acid  and Lewis base.
417 Identify Lewis acid and Lewis base species. 
Understand the relationship between the strength of an acid and that of its conjugate
418 base.
419 Decide whether reactants or products are favored in an acid–base reaction. 
420 Note the two factors that determine relative acid strengths.
421 Understand the periodic trends in the strengths of the binary acids HX.
422 Understand the rules for determining the relative strengths of oxoacids.
423 Understand the relative acid strengths of a polyprotic acid and its anions.
424 Define self-ionization  (or autoionization).
425 Define the ion-product constant for water.

Calculate the concentrations of H3O+ and OH- in solutions of a strong acid or base. 

426
427 Define pH.
428 Calculate the pH from the hydronium-ion concentration. 
429 Calculate the hydronium-ion concentration from the pH. 
430 Describe the determination of pH by a pH meter and by acid–base indicators.
Acid-Base Equilibria
Write the chemical equation for a weak acid undergoing acid ionization  in aqueous
431 solution.
432 Define acid-ionization constant  and degree of ionization.

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433 Determine K a   from the solution pH. 

Calculate concentrations of species in a weak acid solution using K a   (approximation
434 method). 

State the assumption that allows for using approximations when solving problems.
435
Calculate concentrations of species in a weak acid solution using K a   (quadratic
436 formula). 
437 State the general trend in the ionization constants of a polyprotic acid.
438 Calculate concentrations of species in a solution of a diprotic acid. 
Write the chemical equation for a weak base undergoing ionization in aqueous
439 solution.
440 Define base-ionization constant.
441 Calculate concentrations of species in a weak base solution using K b . 
442 Write the hydrolysis  reaction of an ion to form an acidic solution.
443 Write the hydrolysis reaction of an ion to form a basic solution.
444 Predict whether a salt solution is acidic, basic, or neutral.
445 Obtain K a  from K b  or K b  from K a . 
446 Calculating concentrations of species in a salt solution. 
447 Explain the common-ion effect.
448 Calculate the common-ion effect on acid ionization (effect of a strong acid). 
449 Calculate the common-ion effect on acid ionization (effect of a conjugate base). 
450 Define buffer  and buffer capacity.
451 Describe the pH change of a buffer solution with the addition of acid or base.
452 Calculate the pH of a buffer from given volumes of solution. 
453 Calculate the pH of a buffer when a strong acid or a strong base is added. 
454 Define equivalence point.
455 Describe the curve for the titration of a strong acid by a strong base.
456 Calculate the pH of a solution of a strong acid and a strong base. 
457 Describe the curve for the titration of a weak acid by a strong base.
Calculate the pH at the equivalence point in the titration of a weak acid by a strong
458 base.
459 Describe the curve for the titration of a weak base by a strong acid.
Calculate the pH of a solution at several points of a titration of weak base by a strong
460 acid. 
Solubility and Complex-Ion Equilibria
461 Define the solubility product constant , K sp .
462 Write solubility product expressions. 
463 Define molar solubility.
464 Calculate K sp   from the solubility (simple example). 
465 Calculate K sp   from the solubility (more complicated example). 
466 Calculate the solubility from K sp . 
Explain how the solubility of a salt is affected by another salt that has the same cation
467 or anion. (common ion )
468 Calculate the solubility of a slightly soluble salt in a solution of a common ion. 
469 Define ion product.
470 State the criterion for precipitation.
471 Predict whether precipitation will occur, given ion concentrations. 
Predict whether precipitation will occur, given solution volumes and concentrations. 
472
473 Define fractional precipitation.
474 Explain how two ions can be separated using fractional precipitation.
475 Explain the qualitative effect of pH on solubility of a slightly soluble salt.
476 Determine the qualitative effect of pH on solubility. 
477 Explain the basis for the sulfide scheme to separate a mixture of metal ions.

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478 Define complex ion  and ligand.

Define formation constant  or stability constant, K f ,  and dissociation constant, K d .

479
480 Calculate the concentration of a metal ion in equilibrium with a complex ion. 
481 Define amphoteric hydroxide.
482 Predict whether a precipitate will form in the presence of the complex ion. 
Calculate the solubility of a slightly soluble ionic compound in a solution of the
483 complex ion. 
Energetics
484 Define internal energy, state function, work,  and first law of thermodynamics.
Explain why the work done by the system as a result of expansion or contraction
485 during a chemical reaction is -P ∆V .
486 Relate the change of internal energy, ∆U , and heat of reaction, q .
487 Define enthalpy,  H.
Show how heat of reaction at constant pressure, q p , equals the change of enthalpy,
488 ∆H.
489 Define spontaneous process.
490 Define entropy.
491 Relate entropy to disorder in a molecular system (energy dispersal).
492 State the second law of thermodynamics  in terms of system plus surroundings.
493 State the second law of thermodynamics in terms of the system only.
494 Calculate the entropy change for a phase transition. 
495 Describe how ∆H  - T ∆S  functions as a criterion of a spontaneous reaction.
496 Define standard entropy (absolute entropy) .
497 State the situations in which the entropy usually increases.
498 Predict the sign of the entropy change of a reaction. 
Express the standard change of entropy of a reaction in terms of standard entropies of
499 products and reactants.
500 Calculate ∆S ° for a reaction. 
501 Define free energy, G.
502 Define the standard free-energy change.
503 Calculate ∆G ° from ∆H ° and ∆S °. 
504 Define the standard free energy of formation,  DG °.
505 Calculate ∆G ° from standard free energies of formation. 
506 State the rules for using ∆G ° as a criterion for spontaneity.
507 Interpret the sign of ∆G °. 
508 Relate the free-energy change to maximum useful work.
509 Describe how the free energy changes during a chemical reaction.
510 Define the thermodynamic equilibrium constant, K.
511 Write the expression for a thermodynamic equilibrium constant. 
Indicate how the free-energy change of a reaction and the reaction quotient are
512 related.
Relate the standard free-energy change to the thermodynamic equilibrium constant.
513
514 Calculate K  from the standard free-energy change (molecular equation). 
515 Calculate K  from the standard free-energy change (net ionic equation). 
Describe how ∆G ° at a given temperature ( ∆G °T ) is approximately related to ∆H ° and
516 ∆S ° at that temperature.
Describe how the spontaneity or nonspontaneity of a reaction is related to each of the
517 four possible combinations of signs of ∆H ° and ∆S °.
518 Calculate ∆G ° and K  at various temperatures. 
Thermochemistry
519 State the law of conservation of energy.
520 Define a thermodynamic system and its surroundings.
521 Define heat and heat of reaction.

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522 Distinguish between an exothermic process and an endothermic process.

523 Define enthalpy and enthalpy of reaction.
524 Explain how the terms enthalpy of reaction and heat of reaction are related.
525 Explain how enthalpy and internal energy are related.
526 Define a thermochemical equation.
527 Write a thermochemical equation given pertinent information. 
Learn the two rules for manipulating (reversing and multiplying) thermochemical
528 equations.
529 Manipulate a thermochemical equation using these rules. 
Calculate the heat absorbed or evolved from a reaction given its enthalpy of reaction
530 and the mass of a reactant or product. 
531 Define heat capacity and specific heat.
Relate the heat absorbed or evolved to the specific heat, mass, and temperature
532 change.
533 Calculate using this relation between heat and specific heat. 
534 Define calorimeter.
Calculate the enthalpy of reaction from calorimetric data (its temperature change and
535 heat capacity). 
536 State Hess’s law of heat summation.
Apply Hess’s law to obtain the enthalpy change for one reaction from the enthalpy
537 changes of a number of other reactions. 
538 Define standard state and reference form.
539 Define standard enthalpy of formation.
Calculate the heat of a phase transition using standard enthalpies of formation for the
540 different phases. 
Calculate the heat (enthalpy) of reaction from the standard enthalpies of formation of
541 the substances in the reaction.
Electrochemistry
Learn the steps for balancing oxidation–reduction reactions in acidic solution using the
542 half-reaction method.
543 Balance equations by the half-reaction method (acidic solution). 
Learn the additional steps for balancing oxidation–reduction reactions in basic
544 solution using the half-reaction method.
545 Balancing equations by the half-reaction method (basic solution). 
546 Define electrochemical cell, voltaic (galvanic) cell, electrolytic cell,  and half-cell.
547 Describe the function of the salt bridge  in a voltaic cell.
State the reactions that occurs at the anode  and the cathode  in an electrochemical
548 cell.
549 Define cell reaction.
550 Sketch and label a voltaic cell.
551 Write the cell reaction from the cell notation. 
552 Define cell potential  and volt.
553 Calculate the quantity of work from a given amount of cell reactant.
554 Explain how the electrode potential of a cell is an intensive property.
555 Define standard cell potential  and standard electrode potential.
556 Interpret the table of standard reduction potentials.
557 Determine the relative strengths of oxidizing and reducing agents. 
558 Determine the direction of spontaneity from electrode potentials. 
559 Calculate cell potential from standard potentials. 
560 Calculate the free-energy change from electrode potentials.
561 Calculate the cell potential from free-energy change. 
562 Calculate the equilibrium constant from cell potential. 
563 Calculate the cell potential for nonstandard conditions. 
564 Describe how pH can be determined using a glass electrode.
Describe the construction and reactions of a zinc–carbon dry cell,  a lithium–iodine
565 battery,  a lead storage cell,  and a nickel-cadmium cell.

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566 Explain the operation of a proton-exchange membrane fuel cell.

567 Explain the electrochemical process of the rusting of iron.
568 Define cathodic protection.
569 Define electrolysis.
570 Learn the half-reactions for water undergoing oxidation and reduction.
571 Predict the half-reactions in an aqueous electrolysis. 
572 Calculate the amount of charge from the amount of product in an electrolysis. 
573 Calculate the amount of product from the amount of charge in an electrolysis.
Nuclear Chemistry
574 Define radioactive decay  and nuclear bombardment reaction.
575 Learn the nuclear symbols for positron, gamma photon, electron, neutron, proton.
576 Write a nuclear equation. 
577 Deduce a product or reactant in a nuclear equation.
578 Describe the shell model of the nucleus.
579 Explain the band of stability.
580 Predict the relative stabilities of nuclides. 
581 List the six types of radioactive decay.
582 Predict the type of radioactive decay. 
583 Define radioactive decay series.
584 Define transmutation.
585 Use the notation for a bombardment reaction. 
586 Locate the transuranium elements  on the periodic table.
587 Determine the product nucleus in a nuclear bombardment reaction. 
588 Define radioactive decay constant.
589 Calculate the decay constant from activity. 
590 Define half-life.
591 Draw a typical half-life decay curve of a radioactive element.
592 Calculate the half-life from the decay constant. 
593 Calculate the decay constant and activity from half-life. 
594 Determine the fraction of nuclei remaining after a specified time.
595 Apply the carbon-14 dating method.
596 State the ways in which radioactive isotopes are used for chemical analysis.
597 Calculate the energy change for a nuclear reaction. 
598 Properties of alpha,beta and gamma rays
599 Define nuclear binding energy  and mass defect.
600 Compare and contrast nuclear fission  and nuclear fusion.
Explain how a controlled chain reaction  is applied in a nuclear fission reactor  using
601 a critical mass  of fissionable material.
602 Write the reaction of the nuclear fusion of deuterium and tritium.

Inorganic Chemistry
Chemistry of the Main-Group Elements
603 Note the low ionization energies and electronegativities of the metals.
604 Give the principal oxidation states of the main-group elements.
605 State the periodic trends in metallic characteristics.
Metals: Characteristics and Production
606 Define metal, alloy, mineral,  and ore.
607 Define metallurgy.
608 State the basic steps in the production of a metal.
609 Define the Bayer process .
610 Describe the roasting of lead sulfide ore.
611 Describe the electrolysis of molten lithium chloride.
612 Define the Dow process.
613 Define the Hall–Héroult process.

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614 Describe the chemical reduction of lead(II) oxide to lead metal.

615 Give some methods for refining metals.
Bonding in Metals
616 Describe the electron-sea model of metals.
617 Describe the molecular orbital theory of sodium and magnesium metals.
Group IA: The Alkali Metals
618 Note the reactivity of the alkali metals.
619 Describe the metallurgy, reactions, and compounds of lithium.
620 Describe the metallurgy, reactions, and compounds of sodium.
621 Define the Solvay process.
622 Describe some compounds of potassium.
Group IIA: The Alkaline Earth Metals
623 Describe the metallurgy, reactions, and compounds of magnesium.
624 Describe the metallurgy, reactions, and compounds of calcium.
Group IIIA and Group IVA Metals
625 Describe the metallurgy, reactions, and compounds of aluminum.
626 Define the Goldschmidt process.
627 Describe the metallurgy, reactions, and compounds of tin and lead.
Hydrogen
628 Describe some properties of hydrogen.
629 Describe the commercial preparation of hydrogen.
630 Define the steam-reforming process.
631 Describe some reactions and compounds of hydrogen.
632 Define a binary hydride.
Group IVA: The Carbon Family
633 Define catenation.
634 Describe some allotropes of carbon.
635 Describe the chemical properties of the oxides of carbon.
636 Describe the chemical properties of the carbonates.
637 Describe the preparation of extremely pure silicon.
638 Define silica.
639 Describe the uses of quartz.
640 Define silicate, condensation reaction,  and silicone.
Group VA: Nitrogen and the Phosphorus Family
641 Describe the properties and uses of nitrogen.
642 Describe some nitrogen compounds.
643 Define the Ostwald process.
644 Describe the allotropes of phosphorus.
645 Describe the phosphorus oxides and the oxoacids of phosphorus.
646 Define polyphosphoric acids  and metaphosphoric acids.
Group VIA: Oxygen and the Sulfur Family
647 Describe the properties and preparation of oxygen.
648 Describe some reactions of oxygen.
649 Define oxide, peroxide,  and superoxide.
650 Describe the allotropes of sulfur.
651 Describe the production of sulfur.
652 Define the Frasch process  and the Claus process.
653 Describe the sulfur oxides and oxoacids.
654 Define the contact process.
Group VIIA: The Halogens
655 Describe chlorine and its properties, preparation, and uses.
656 Describe the preparation of hydrogen chloride and its uses.
657 Describe the preparation and uses of the oxoacids of chlorine.
Group VIIIA: The Noble Gases
658 Describe the discovery, preparation, and uses of the noble gases.
659 Describe some compounds of the noble gases.

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The Transition Elements and Coordination Compounds

Periodic Trends in the Transition Elements
660 Identify the transition elements  on the periodic table.
State the three characteristics that set the transition elements apart from the main-
661 group elements.
662 Write electron configurations of the transition elements.
663 Describe trends in atomic radii of the transition elements.
664 Learn the common oxidation states of the fourth-period transition elements.
The Chemistry of Two Transition Elements
665 Learn some of the common chromium compounds and their chemistry.
666 Learn some of the common copper compounds and their chemistry.
Formation and Structure of Complexes
Define complex ion, complex (coordination compound) ligand, and coordination
667 number.
Give examples of a monodentate ligand, bidentate ligand,  and polydentate ligand.
668
Naming Coordination Compounds
669 Learn the four rules for naming coordination compounds.

Write the IUPAC name given the structural formula of a coordination compound. 
670

Write the structural formula given the IUPAC name of a coordination compound.
680
Structure and Isomerism in Coordination Compounds
681 Define constitutional isomers, stereoisomers , and geometric isomers.
682 Decide whether geometric isomers are possible. 
683 Define enantiomers  (optical isomers ).
684 Explain how structures are used to determine if an isomer is chiral.
685 Describe how enantiomers are optically active.
686 Define dextrorotatory, levorotatory,  and racemic mixture.
687 Decide whether optical isomers are possible. 
Extractive Metallurgy
688 Carbon Reduction Method
689 Self Reduction Method
690 Electrolytic reduction Method
691 Cyanide Process
Principles of Qualitative Analysis
692 Group I to V as mentioned in the syllabus
693 Nitrates, Halides ( excluding florides ), Sulphates and Sulphide

Organic Chemistry
Fundamentals of Molecular Structure and Chemical Reactivity
Sketch the 1s, 2s and 2p atomic orbitals (with mathematical signs) and write the
electronic configuration for all elements in the first two rows of the periodic chart.
694
Show in a sketch how the sp3, sp2 and sp hybrid orbitals may be constructed from the
695 simple atomic orbitals.
Explain the bond angle for the hydrides of all the elements through F using both the
696 VSEPR and hybridization models.
697 Deduce molecular formula from composition and molecular weight.
698 Calculate the formal charge on an atom in a small molecule.
Predict the direction and relative magnitudes of the dipole moments of simple
699 molecules.
Sketch a reasonable set of molecular orbitals for any 2-carbon molecule, showing the
700 mathematical signs of the lobes and approximate relative energies.

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Describe the molecular events occurring during melting and boiling for ionic and
701 covalent compounds and molecular crystals like diamond.
Predict the relative solubilities, melting points, boiling points and relative acidities
and basicities of simple compounds and explain your choice with reference to
702 structure.

Explain by words and equations the factors affecting the rate of a chemical reaction.
703
704 Identify the major functional groups and types of reactions.
Calculate the pH of a solution of a weak acid or base from the analytical concentration
705 and Ka.
Calculate the concentrations of components in a chemical equilibrium from the
706 equilibrium constant and analytical concentrations.
The Alkanes and Cycloalkanes: Nomenclature, Conformation and
Configuration
Name by the IUPAC system any saturated hydrocarbon whose parent chain contains
10 or fewer carbon atoms and no more than two simple rings (or sketch the
707 hydrocarbon given its IUPAC name).

Sketch the conformations of ethane, propane, butane, cyclobutane, cyclopentane and

cyclohexane and simple substituted compounds derived from them.
708

Describe (graphically ) the relation between conformation and potential energy for
ethane, propane and butane and closely related compounds (Newman projections).
709
Describe (graphically) the relation between conformation and potential energy for
710 cyclohexane.
Calculate the relative energies of disubstituted (e.g. methyl) cyclohexanes, assuming
chair conformations and using the relative energies of monosubstituted cyclohexane or
711 butane.
Define and recognize stereoisomer, enantiomer, diastereomer, conformation,
712 configuration, meso, epimer, resolution.
Given their structures, state whether 2 compounds are enantiomers or diastereomers
713 or some other kind of isomer.
714 Predict the number of stereoisomers of a compound of known bonding.
Sketch a molecule with a chiral center so as to show unambiguously the configuration
715 using both Fisher projection and perspective drawing.
Predict from the structure whether a pair of stereoisomers can be interconverted by a
716 conformational change and thus might not be separable.
717 Draw conclusions about the mechanism of a reaction from the stereochemistry.
718 Given a proposed mechanism for a reaction, predict the stereochemistry.
Outline a synthesis (several steps) of a hydrocarbon using halogenation and metal
719 reductions.
Outline syntheses of cyclopropane compounds using carbene-generating compounds.
720
The Alkenes, Alkadienes and Alkynes
ALKENES
Sketch the molecular orbitals (bonding and antibonding) for ethene and their relative
721 energies.
Name by the IUPAC system any alkene whose parent chain contains 10 or fewer
722 carbon atoms and sketch the alkene given its IUPAC name.
Define, recognize and name alkene diastereomers (cis/trans); predict the direction of
723 the difference in their physical properties and chemical stability.
Outline the synthesis of a given alkene from an alkyl (di)halide, alcohol, alkyne or
724 alkane (including stereochemistry).
Write chemical equations to describe the currently accepted mechanism(s) of
dehydrohalogenation of an alkyl halide (including stereochemistry). Explain how this
725 mechanism is deduced from the experimental data.

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Write chemical equations to describe the currently accepted mechanism(s) of

dehydration of an alcohol (including stereochemistry). Explain how this mechanism is
726 deduced from the experimental data.

Describe the evidence for the existence of carbocations and their relative stabilities.
727
728 Predict and recognize simple carbocation rearrangements (H, CH3, C6H5).
729 Predict the alkenes formed by elimination reactions of given starting materials.
Predict the products or use in a synthetic plan the following reactions of alkenes
(including stereochemistry): catalytic hydrogenation, addition of halogen and
hypohalite, addition of hydrogen halide, addition of water, oxymercuration, addition of
carbocations (polymerization and alkylation), hydroxylation, epoxidation, addition of
730 carbenes, hydroboration, ozonolysis.
Use the molecular formula, and oxidation and reduction reactions to deduce structural
731 features of an alkene.
Write chemical equations to describe the currently accepted mechanism of addition of
halogens to alkenes (including stereochemistry). Explain how the mechanism is
732 deduced from the experimental data.
Write chemical equations to describe our current understanding of the mechanism of
addition of acids (HX, H3O+, H2SO4) to alkenes. Explain how the mechanism is
733 deduced from the experimental data.
Using a reasonable mechanism for the reaction, explain why the orientation of
addition of HBr is sometimes "anti-Markovnikov" and what experimental evidence
734 exists for the explanation.
Write the mechanism for the acid-catalyzed addition of an alkene to itself. Do the
735 same for free radical addition.
736 Write the mechanism for the Wurtz reaction and decarboxylation reaction
CONJUGATED ALKENES -- DIENES
Use allylic halogen substitution as part of a synthetic outline, (distinguish conditions
737 yielding ionic addition and free-radical substitution).
Write contributors to the resonance hybrid for simple systems such as allyl radical
738 (cation), carbonate, nitro.
Sketch the pi molecular orbitals of butadiene and allyl and indicate their relative
739 energies in a sketch.
Predict the products, in order of relative amount, of the addition of halogen or acid to a
diene; give an explanation of the effect of temperature on the product distribution.
740
By considering the mechanism and the stabilities of intermediates, explain the
differences between the reactions of conjugated double bonds and isolated double
741 bonds.
742 Outline the mechanism and stereochemistry of the Diels-Alder reaction
ALKYNES
Predict the products and use in a synthetic scheme the following reactions of alkynes:
addition of hydrogen, halogen, hydrogen halides, water, boron hydrides, and salt
742 formation with very strong base or reducing metals.
Outline a synthesis of an alkyne from an alkene, alkyl halide, dihalide or tetrahalide;
743 outline the synthesis of an internal alkyne from a terminal alkyne.
744 Reactions of Alkenes and Alkynes with KMnO4 and ozone
Preparation of Alkenes and Alkyne by elimination reaction , Electrophilic reaction
745
746 Preparation of Alkyne by addition reaction
Predict products and stereochemistry of a Diels-Alder reaction. Make a sketch of a
747 reasonable transition state for this reaction.
Alkyl Halides
Name any alkyl halide whose parent chain is 10 carbons or less by the IUPAC system
748 and sketch an alkyl halide given its IUPAC name or alkyl name.

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Write the mechanism for halogenation of methane. Describe the experiments from
which the mechanism was deduced and the reasoning which lead to the mechanism.
749
Calculate bond dissociation energies and heats of reaction given the energies for
various steps and draw mechanistic conclusions from this energy data (similarly heats
750 of activation).
Given energy data (or relative rate data) and other experimental information about a
751 reaction, sketch a graph of energy vs. reaction progress.
Predict the products (including order of abundance) of halogenation of an alkane and
752 explain your choice by reference to the mechanism.
753 Explain the difference between a transition state and an intermediate.
Explain the greater selectivity achieved in bromination compared to chlorination.
754
Use the existing experimental evidence to describe the basis of our current
understanding of the mechanisms of nucleophilic substitution at sp3 carbon. Write
755 chemical equations to outline the mechanism for a particular halide.
Use nucleophilic substitution in a synthetic plan of several steps, taking into
consideration elimination, rearrangement and stereochemistry. Note that some of
756 these reactions form carbon-carbon bonds.
Predict the products, including stereochemistry, of a nucleophilic substitution of an
757 alkyl halide.
Predict (and explain) the effect of alkyl, vinyl and aryl substituents on nucleophilic
758 substitution.
Given the identity of nucleophile, leaving group, substrate and solvent, predict
whether elimination or substitution will predominate for a particular alkyl halide
759 substrate.
Outline in chemical equations the mechanisms of elimination of alkyl halides. Describe
the experimental information collected about this reaction and how the mechanisms
760 are deduced from this information.
761 Define and use correctly the terms SN2, SN1, E2, E1.
762 Outline syntheses using organomagnesium and organocopper compounds.
763 Draw conclusions about the mechanism of a reaction from the stereochemistry.
764 Given a proposed mechanism for a reaction, predict the stereochemistry.
Given the predominant diastereomer in a stereoselective or stereospecific reaction,
765 provide a mechanistic explanation for the preference.
Describe the evidence for the existence of carbocations and their relative stabilities.
766
767 Predict and recognize simple carbocation rearrangements (H, CH3, C6H5).
Alcohols and Ethers
ALCOHOLS
Name any alcohol whose parent carbon chain consists of 10 or fewer atoms by the
IUPAC system and sketch the alcohol given its IUPAC name or carbinol name.
768
Predict the relative acidity of alcohols by referring to the stability of all species in the
769 equilibrium.
Using our current understanding of the mechanisms of the two addition reactions,
explain why simple acid- catalyzed addition of water can give a different product in
both stereochemistry and orientation from the hydroboration-oxidation. Note that the
oxymercuration (Hg(OAc)2) / reduction is more regioselective than simple acid-
770 catalyzed addition of water.
Show how the mechanism of the hydroboration reaction is deduced from the
experimental data about the reaction. Write chemical equations to describe the
771 mechanism, showing transition states if necessary.
Write a reasonable mechanism for the Grignard and lithium aluminum hydride
772 synthesis of alcohols from carbonyl compounds.

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Outline a several-step synthesis involving preparation of an alcohol from an alkene

(two ways), a ketone or aldehyde, an alkyl halide, an ester, an epoxide or an ether.
773
Outline the currently accepted mechanisms of the substitution of an alcohol by halogen
774 using HX and describe the experimental evidence for the mechanism.
Use HX and thionyl chloride or the phosphorus halides for the conversion of an alcohol
775 to an alkyl halide in a synthetic plan (the differences may be important).
Use the oxidation reactions of alcohols to aldehydes, ketones and carboxylic acids in a
776 synthetic plan.

Given all the reagents and products in an alcohol oxidation by dichromate or

permanganate, determine the number of moles of each ingredient, i.e. balance the
equation. Outline the mechanism of the oxidation of an alcohol by chromate.
777
Aromatic Compounds
STRUCTURE and NOMENCLATURE
Explain the unusual stability of conjugated double bond systems by the valence bond
(resonance) and the molecular orbital (Huckel, aromaticity) methods; distinguish the
778 two approaches.
Write contributor structures to the resonance hybrid for simple molecules (e.g. allyl
radical, butadiene, benzyl cation, vinyl ether, p-nitrophenol) and order the structures
779 in decreasing importance as contributors.

Explain the experimental basis for the concept of resonance or aromaticity, i.e. the
differences in properties between aromatic and similar non-aromatic compounds.
780
Sketch the molecular orbitals computed by the Huckel method for benzene, butadiene,
781 and allyl; assign relative energies.
Predict whether a molecule will be aromatic or antiaromatic (for single and condensed
rings, ions, and heterocycles). Prerequisite: determine if the concept of aromaticity is
782 applicable.
Use correctly the following terms: resonance, delocalized, resonance energy, hybrid,
783 orbital, bonding, antibonding, non-bonding, aromatic, antiaromatic.
Use the concept of resonance and/or aromaticity to account for polarity, basicity,
acidity, etc. of benzene derivatives such as phenol, aniline, nitrobenzene, compared to
784 non-conjugated analogs.
Name by the IUPAC system compounds with substituted benzene rings (e.g. p-
785 nitroaniline) and sketch substituted benzenes given their IUPAC names.
ELECTROPHILIC AROMATIC SUBSTITUTION
Write the mechanism of electrophilic substitution of benzene for nitration,
halogenation, alkylation, acylation, protonation, and sulfonation, including production
of the electrophile. Sketch contributors to the intermediate resonance-stabilized ion
786
and the electrophiles. Give experimental evidence for the mechanism.
Explain, by referring to the mechanism of the reaction, the effect of a previous
substituent on the reactivity and orientation of electrophilic aromatic substitution
787 (consider resonance, inductive and steric effects).
Outline a several-step synthesis of a substituted benzene which requires careful choice
of order of substitution to put the substituents in the correct orientation. This
synthesis may involve, in addition to the reactions in 9, oxidation or reduction of a
substituent or use of a protecting group (e.g. acyl) and the choice of mild conditions for
788 substitution of aniline and phenol.
Explain the ease with which substitution and elimination reactions occur at the carbon
789 to a benzene ring by application of the principles of resonance.
NUCLEOPHILIC AROMATIC SUBSTITUTION
Outline the mechanism of nucleophilic aromatic substitution and describe the
790 experimental evidence for our current understanding of the mechanism.

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Predict and explain the relative reactivity of substituted aryl halides toward
791 nucleophilic substitution by deduction from the mechanism of the reaction.
792 Use nucleophilic aromatic substitution as a step in synthetic sequence.

From the experimental evidence, explain why nucleophilic aromatic substitutions in

the presence of very strong bases (like NH2-, C6H5-) proceed by elimination followed
by addition rather than through an anionic intermediate (benzyne).
793
MISCELLANEOUS
Outline a synthesis using the preparation of a benzenediazonium salt and its
substitution by halogen, hydrogen, cyanide, hydroxide with the correct reagents, and
794 the conversion of a diazonium salt into an azo dye. See Unit XI.
795 Outline the synthesis of salicylic acid from phenol.
796 Use the oxidation and reduction of aromatic rings in a synthesis.
797 Identify likely cumulative toxins among aromatic compounds.
Carboxylic Acids and Their Derivatives
Name by the IUPAC system any carboxylic acid, ester, amide or anhydride with 10 or
fewer carbon atoms in the parent chain and sketch the above given their IUPAC
798 names (and common names up to 4 carbons).
Analyze the causes of the relative acidities of carboxylic acids by considering the
inductive, resonance and steric effects on the neutral (conjugate acid) form and the
anionic (conjugate base) form; use a similar analysis to predict the acidities of others.
799
Similarly analyze phenols, alcohols and compare with carboxylic acids
Outline the synthesis of a given carboxylic acid from the appropriate alcohol, aldehyde,
methyl ketone, alkyl benzene, alkyl (aryl) halide, nitrile, amide, ester, anhydride, acyl
800 halide.

Outline the synthesis of an acyl halide, amide, substituted amide, ester (lactone) or
anhydride from a carboxylic acid directly or from acyl halide or anhydride or ester.
801
Outline the synthesis of compounds with the following functional groups from
carboxylic acids or their derivatives: alcohol (p, s, t), -haloacid, -aminoacid, ketone,
802 aldehyde.
803 Describe and recognize lipids, phospholipids, soaps, nylon, proteins, polyesters.

Write the currently accepted mechanism for the acid-catalyzed hydrolysis of ester,
amide, anhydride or acyl halide to the corresponding carboxylic acid. Similarly base-
catalyzed hydrolysis. Explain the experimental basis for each mechanism.
804
Write the currently accepted mechanism for the acid-catalyzed preparation of an ester
from an acid and an alcohol and explain the experimental evidence from which it was
805 deduced.
Write the currently accepted mechanism for acid or base-catalyzed ester exchange
806 (transesterification) (exactly like hydrolysis and esterification).
Outline the mechanism and stereochemistry of the Diels-Alder reaction, e.g. for maleic
807 anhydride.
Aldehydes and Ketones as Electrophiles
Name any aldehyde or ketone which contains ten or fewer carbon atoms in its parent
808 chain by the IUPAC system.
Given alkanes, alkenes, alkyl halides, alcohols, ethers, carboxylic acids, ketones
(aldehydes) of similar molecular weight, order them in polarity, boiling point, and
809 solubility in water.
Outline a synthesis of an aldehyde or ketone from a given alcohol, carboxylic acid,
810 alkene, alkyne, or alkyl benzene (or a precursor of these).
Write the currently accepted mechanism of Friedel-Crafts acylation of aromatic
811 compounds and describe the experiments leading to this proposed mechanism.
Write the currently accepted mechanisms for the addition of hydride reagents,
812 Grignard reagents, (bisulfite) and cyanide ion to ketones and aldehydes.

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Write the currently accepted mechanisms for the addition of alcohols (and ammonia
and its derivatives) to ketones and aldehydes; describe the experimental basis for these
mechanisms, including the effect of pH. Show why some amines give imines and others
813 enamines.
Advanced topic: Write the mechanism of the Cannizzaro reaction and describe the
814 experimental basis for the mechanism.

Identify starting materials or products for the reactions of aldehydes and ketones with
silver ion (in ammonia), permanganate, dichromate, cyanide, (bisulfite), ammonia,
amines, hydrazine and its derivatives, alcohols, hydride reagents (at least two),
815
hydrogen, and Grignard and other organometallic reagents.
Use organometallic reagents in the synthesis of compounds with new carbon-carbon
816 bonds.
Use the reactions of aldehydes and ketones with oxidants, cyanide, ammonia and its
817 derivatives, alcohols, hydride and hydrogen in a short synthetic plan.
Give a brief summary of the mechanism of the Wittig reaction and use the reaction in
818 a synthetic plan. Recognize an ylide.
Carbonyl Compounds as Nucleophiles: Carbanions
Write the currently accepted mechanisms for the acid-catalyzed and base-catalyzed
819 interconversion of keto and enol forms.
Write the mechanisms for the base-catalyzed and acid-catalyzed halogenation of
aldehydes and ketones and explain how the experimental evidence leads to these
820 mechanisms. Describe the mechanistic basis of the iodoform test.

Write the mechanism of the aldol condensation for any simple reactive aldehydes or
ketones. Describe the experimental evidence for this reaction mechanism.
821
Recognize aldol condensation products and use the crossed aldol condensation in a
822 practical sythesis. 
823 Write the currently accepted mechanism of the Claisen ester condensation.
Write the mechanism of formation of enamines and use them as an enol substitute in a
synthetic sequence forming new C-C bonds, esp. one in which an enolate reaction
824 mixture would be too basic.

Write the currently accepted mechanisms of the malonic and acetoacetic ester
syntheses. Use these reactions in a synthetic plan, including that of a barbiturate.
825
Write the mechanisms of the decarboxylation of ß-carbonyl acids and the base-
826 catalyzed reverse (Claisen) condensation of ß-dicarbonyl compounds.
Write the mechanism of and explain the reason for nucleophilic addition to the ß-
carbon of an , ß-unsaturated carbonyl compound, esp. by carbanions in the Michael
827 reaction.

Recognize products of a Michael reaction and use it in a simple synthetic scheme.

828
Use the above reactions and the Reformatsky (PBr3 + carboxylic acid) and Hell-
829 Vollhard- Zelinski reactions in a short synthetic sequence.
Recognize reactions similar to the Aldol and Claisen condensations with functional
830 groups similar electronically to carboxyls.
Amines and Amino Acids
Name any primary, secondary or tertiary aliphatic amine with 10 carbons or fewer in
the parent chain by the IUPAC system and sketch the amine given its IUPAC name.
831 Name aniline, pyrrole, pyridine and their derivatives.
Given a mixture of up to four organic compounds, outline their separation using a flow
chart, by acid-base and solubility properties and by chemical reactions from which they
832 can be recovered.

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Analyze the causes of the relative basicities of a series of amines by applying the
concepts of resonance, inductive and steric effects to explain the relative stabilities of
base and conjugate acid and predict the relative basicity of another amine. Repeat
using the acidities of the conjugate acids as your starting point (the way most chemists
833 do it).
Outline the synthesis of an amine using its preparation from a nitrile, nitro compound,
alkyl halide, amide or ketone. The synthetic route must be chosen to minimize
mixtures of primary, secondary and tertiary. Note that some synthetic methods change
834 the number of carbon atoms in the molecule.
Write the currently accepted mechanism for the preparation of amines from alkyl
halides. Explain why this technique is particularly useful for the preparation of -
835 aminoacids. Why is the Gabriel synthesis often preferable?
Give several examples of biologically important amines and amides. Recognize indole,
836 quinoline, isoquinoline alkaloids and 2-arylethylamines.
Advanced topic: Write the mechanism of the Hofmann degradation of amides to amines
and comment on the experimental data leading to this complex mechanistic sequence.
837
Outline the steps in the (Hofmann) elimination of amines to form alkenes for
identification. Given the product alkene and other spectroscopic and chemical
838 information, deduce the structure of the original amine.

Outline the currently accepted mechanism of the formation of N-substituted amides

from amines using experimental observations to support the mechanism.
839
840 Explain the high reactivity of aniline toward ring substitution.
841 Explain the chemical basis and practical use of the Hinsburg test.
Propose a mechanism for the reductive amination of a ketone or aldehyde using what
you have already learned about reactions of carbonyl compounds and catalytic
842 reduction with hydrogen.

Outline simple syntheses of amino acids using reactions learned for amines and acids.
843

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