Inorganic Chemistry 2: Table of Contents

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Table of contents
Inorganic chemistry 2
Task 1 (Grade 9) ............................................... ................................. 2
Task 2 (Grade 9) .............................................. ................................. 3
Task 3 (Grade 9) ............................................... ................................. 3
Task 4 (Grade 9) .............................................. .................................. 4
Task 5 (grades 9, 10) .......................................... ............................ 5
Task 6 (grades 9, 10) .......................................... ................................... 7
Task 7 (grades 9, 10, 11) .............................................. ........................ eight
Task 8 (grades 9, 10, 11) .............................................. ...................... 10
Organic chemistry thirteen
Task 1 ................................................. ......................................... thirteen
Task 2 ................................................. ......................................... 14
Task 3 ................................................. ......................................... 15
Task 4 ................................................. ......................................... sixteen
Chemistry and Life eighteen
Task 1 ................................................. ......................................... eighteen
Task 2 ................................................. ......................................... twenty
Physical chemistry 23
Task 1 ................................................. ......................................... 23
Task 2 ................................................. ......................................... 24
Task 3 ................................................. ......................................... 26
Task 4 .................................................. ............................................... 27
Task 5 .................................................. ............................................... 29
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© TsPMK Higher School of Chemistry
Dear participants!
The second theoretical round includes four blocks of problems: "Inorganic
Chemistry", "Organic Chemistry", "Chemistry and Life" and "Physical Chemistry".
Each task is worth 25 points. Four (4) tasks you solved with the maximum result
will be credited to your asset.
Required condition:
- participants from 9 classes choose tasks from at least two (2) different
blocks;
- participants from 10 classes choose problems from at least three (3)
different blocks, and from the “Inorganic Chemistry” block you can choose only
from problems 5, 6, 7, 8;
- participants from 11 classes choose one problem from each block, and
from the block "Inorganic Chemistry" you can choose only from problems 7, 8.
Good luck!
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Inorganic chemistry
Task 1 (Grade 9)
When an electric current of 0.2 A was passed through 50 mL of liquid X , gas evolution immediately (t0)
began on one of the two platinum electrodes (the cathode and anode spaces were separated). After 51 min. 30
sec (t1) the gas began to evolve at the second electrode as well. After some time (t2), the electrolysis was
completed. The gases released on the electrodes at different times were passed through an aqueous solution
of potassium iodide. The observations made in this case are given in the table:
The Observations made when passing through an aqueous solution of potassium iodide ...
moment
of sampling ...gas released on ...gas released on
gas first electrode second electrode
The solution initially acquired a brown color, which
-
t0 after a while
me disappeared.
The solution initially acquired a brown color, which

No visible changes
t1 after a while
gone.
me disappeared.
No visible changes
t2 There were no visible changes
gone.
The electrodes were removed from the solution and weighed. It turned out that the mass of
the second electrode increased by 0.2048 g.
Tasks:
1. Determine the qualitative and quantitative composition of the initial liquid, if it is known that the
masses of precipitates formed by mixing equal volumes of this liquid (50 ml) with aqueous solutions of sodium
phosphate and lead (II) acetate taken in excess are 0.5080 and 1.2541 g, respectively.
2. What time did electrolysis take (t2 -?), if the volumes of gaseous
products released on both electrodes were equal?
3. Write the equations of all the reactions mentioned in the text of the problem.
Note. When calculating, use the formula:
m = (MÿIÿt)/(zÿF),
where m is the mass of the substance formed on the cathode or anode, g; M is its molar mass, g/mol; I –
current strength, A; t is the electrolysis time, s; z is the number of received or given off electrons per 1 molecule
of the substance formed on the electrode, F = 96485 C/mol is the Faraday constant (the charge of 1 mol of
electrons).
When calculating, assume that the current outputs are 100%.

2
Task 2 (Grade 9)
animal + plane
(mystery)
A simple substance A is involved in the chain of transformations:
It is known that B is a white powder, which, when dissolved in water, gives an acid
reaction of the environment, C is a colorless toxic liquid, and G is
colorless poisonous gas. Compound H , the first organic derivative A, which is a foul smelling
liquid (7.08% oxygen, 21.24% carbon by mass), was obtained by the action of chloride E on
aqueous potassium acetate. The reaction is accompanied by the release of carbon dioxide.
Tasks:
1. Determine which substances are discussed in the problem (substances A - G), on
write the equations of all the reactions presented in the scheme (10 reactions).
2. Determine the composition of H and give the equation for the reaction of its formation.
3. Explain why E does not form dimers in the vapor phase, unlike
AlCl3?
4. The reaction G ÿ A has some analytical significance to this day, give the reaction
equations that make it possible to distinguish A, which is formed in the form of a gray coating,
from its heavier analogue according to the periodic table?
Task 3 (Grade 9)
The young chemist took in the laboratory a white powder of binary compound A,
containing element X, and dissolved it in cold water (reaction 1). After that, an excess of
sodium hydroxide solution was added to the resulting solution and a current of chlorine was
passed through it (reaction 2). In this case, a colorless solution of substance B was formed.
A solution of salt B, which also contained an excess of sodium hypochlorite , was

mixed by the young chemist with a solution of a pale pink salt B of metal Y.
* when adding ethyl alcohol, the solubility of the substance G decreases

3
a precipitate of crystalline hydrate G precipitated from the

solution with alcohol . To analyze the resulting substance, the young chemist
heated 0.5000 g of G at 150 ° C until the mass ceased to change, the mass of the
residue was 0.3664 g (reaction 4). Next, the Young Chemist passed 0.5000 g of G into
a current of sulfur dioxide into an aqueous solution (reaction 5). After the reaction
stopped, he heated the solution to remove excess sulfur dioxide from the solution and
divided it into two equal parts. To the first one he added a small excess of silver nitrate
(reaction 6). In this case, a yellowish precipitate D, weighing 0.1452 g, precipitated.
And after separating the precipitate, the young chemist added a small excess of a
solution of barium chloride to the filtrate (reaction 7). He separated the precipitated
white precipitate E , dried it and weighed it, its mass was 0.6252 g. The young chemist
cooled the second part of the solution and added ammonium hydrosulfide solution to it
(reaction 8). In this case, a precipitate of pink color Zh was formed, containing metal
Y, which the Young Chemist separated and dried in a nitrogen atmosphere at 100°C;
the weight of the precipitate was 0.0179 g.
Additional Information:
Substance A is capable of reacting with carbon monoxide even at room
temperature (reaction 9). As a result of this interaction, a simple substance G is
formed, which colors starch, and a colorless gas I, which is part of the air, with a
relative hydrogen density of 21.83.
Substance B is a salt of acid K, which forms an average silver salt L. It is known
that salt C precipitates E with barium salts. In nature, metal Y
occurs as the oxide M.

Mass fractions of elements X and Y in some compounds:
ABCDLM
ÿ(X), % 76.04 43.18 54.05 16.65
ÿ(Y), % 19.84 63.20
Tasks:
1. Determine the elements X, Y, substances A-M. Justify the answer. Composition A,
B, C, D , L, M confirm by calculation.
2. Write the reaction equations (1–9). Write reactions 6–8 in the abbreviated
ionic form.
3. Why did the young chemist dry substance G in a nitrogen atmosphere?
What happens if this substance is heated in air, write the equation for the reaction.
Task 4 (Grade 9)
Salts of an inorganic acid X1 containing element A can be obtained by the
interaction of a binary gaseous compound A1 and acidic
4
acid salts X2 (reaction 1). A solution of anhydrous acid X1 in diel ether decomposes
above ÿ5°C into compounds A1 and A2 , stable acid anhydride X3 (reaction 2).
Sodium salt A3 of acid X1 was used as a "fixer" in photography to dissolve silver
bromide (reaction 3). Salt A4 can be isolated from this solution , containing
19.32% silver and 34.35% element A.
Acid salts of acid X2 are moderately strong reducing agents. In the reaction
with iodine used in volumetric analysis, acid X3 salts are obtained (reaction 4). The
interaction of zinc dust at low temperatures with acid anhydride X2 yields a salt of
acid X4 (reaction 5). Anhydrous sodium salt A5 of acid X4 contains 26.43% sodium.
Salt A5 when heated as one of the products gives A3 (reaction 6)
Acid X5 is a part of antiscale and is used for cleaning industrial devices. It can
be obtained by reacting A2 with an equimolar amount of ammonia (reaction 7).
Salts of acid X5 are used in pyrotechnics. Potassium salt A6 of acid X5 is obtained
by reacting acid X5 with an acid salt of acid X3 in the presence of calcium hydroxide
(reaction 8).
Tasks:
1. Identify element A. Justify your answer.
2. Set the formulas of compounds X1 - X5 and A1 - A6. In all the mentioned
connection includes element A.
3. Write the equations for reactions 1 – 8. Write reactions 1, 4, 5 in abbreviated
ionic form.
4. In the gas phase , A2 molecules are in equilibrium with the trimer. Draw the
structure of the A2 molecule , A2 trimer , X4 acid anion , and X5 acid.
Task 5 (grades 9, 10)

Element X is of great importance in metallurgy, in the production
galvanic cells and in fine organic synthesis, and its compounds show an extremely
diverse color. Under laboratory conditions, compounds of element X in all oxidation
states accessible to it can be obtained starting from substance A, a dilute aqueous
solution (raspberry color) of which is widely used in everyday life as an antiseptic.
Examples of such syntheses are shown in the scheme.
5
All encrypted substances contain the element X. A, C – M are crystalline substances,

binary compound B is a liquid. The color of the compounds and the content of element X in
some of them are given in the table.
Mass content of element
Compound Connection color
X, %
A Dark purple Dark 34.76
B green (in reflected light), dark red (in 49.55

transmitted light) Black Dark brown (brown)
C 15.88
D
dark green
EF Blue
Golden Light Pink GH 22.42
Bluish Violet J White 13.03
KL Light pink Red-violet M Upon slight 30.69

substance C , among heating
the products
of 0.1ofmol
its of 11.20
decomposition, one can detect 14.9 g of KCl and an asphyxiating yellow-green gas
(reaction 14), the complete absorption of which requires 160 ml of 1.25 M hot NaOH
solution (reaction 15).
When 0.1 mol of substance F is dissolved in water, a green solution of substance E

(pH > 7) is formed, and a precipitate D with a mass of 4.35 g is formed (reaction 16). Neutrals
The addition of a green solution leads to the gradual precipitation of an additional amount
of precipitate D and a change in the color of the solution to raspberry, associated with the
formation of A (reaction 17).
In compounds G, J , and L , the oxidation state of X is the same; in J , K and M
6
the dination number of the central ion is six; ethanol in reaction 8, three ethylaluminum in
reaction 9 , and aluminum in reaction 11 are reducing agents.
Tasks:
1. Write all the reaction equations shown in the diagram (13 equations).
Establish and confirm by calculation the composition of compounds A, B, C, G, J, L and M.
2. Write the equations for reactions 14 - 17.
3. Draw the structure of compound H.
Task 6 (grades 9, 10)

X is a silvery white transition metal that is part of an alloy with a shape memory
effect* . A fine powder of metal X reacts when heated with oxygen to form oxide A, this
compound is the white pigment in paints. By sintering metal X with its oxide A , B can be
obtained . When A reacts with coal and chlorine at high temperature, gaseous gas is
formed under reaction conditions C, under normal conditions this
liquid.
Metal X dissolves in hydrochloric acid, forming a violet solution of substance D.

Metal X reacts with iodine in acetonitrile (CH3CN), paramagnetic substance E can be
isolated from the resulting solution in crystalline form. In this ionic compound, the metal
cation X is located in octahedral environment† of nitrogen atoms, and all anions are
identical.
Substance C is hygroscopic and "smokes" in air. When C interacts with cold water,
a white substance F is formed, by heating which one can obtain A. Substance F is called
an acid, but it practically does not react with alkalis, but it dissolves in hydrofluoric acid to
form substance G, which exists only in solution. If hydrogen peroxide is added to solution
G and the excess hydrofluoric acid is neutralized with an ammonia solution, then at pH =
6 the diamagnetic substance H precipitates almost quantitatively.
When C is added to a solution of sodium cyclopentadienyl in tetrahydrofuran (THF),

substance I is formed, which can be recrystallized from
toluene.
J is synthesized by adding a solution of I to a solution of sodium and naphthalene in THF
* Shape memory alloy products return to their original shape after being deformed when heated
† Around the X atom, the nearest neighbors are located at the vertices of an octahedron (a
regular polyhedron with six vertices)
7
at 25°C. Pyrophoric crystals J are obtained by recrystallization from benzene.

I2 ÿ2 ,tÿC C,Cl2 NaC5H5 NaC10H8
E CH3CN
X A tÿC
C THF
I J
THF, 25 ÿC
tÿC
HF40% H2O2(30%)
D B F G Hÿ
pH=6 (NH3 )
Quantity ÿ( ÿ), % Color Quantity ÿ( ÿ), % Color ÿ 66.6 violet H

20.9 bright yellow
E 3.33 19.2 bright red
black I
F White
41.3 26.9 green J
1) Determine the metal X and substances A-J, justify the answer. Confirm the
composition of B, E, F, H, I, J by calculation.
2) Write the equations of all reactions according to the given scheme.
3) Write the equation for the reaction of F with a solution of NaOH and A with a melt
NaOH.
4) Give the chemical composition and name of the mineral metal X.
Task 7 (grades 9, 10, 11)

The volatile red binary substance Y (the mass fraction of the heavier element
is 63.12%) is one of the strongest oxidizing agents and can be obtained from simple
substances by heating one of them in an electric arc in the atmosphere of another
(reaction 1). When heated , Y is able to decompose, giving, among other products,
Y1 (reaction 2). When expanding only up to Y1
the weight loss is 6.15%. Y1 also has a red color, in the solid phase it is a tetramer,
and in the gas phase it is monomeric and can disproportionate into Y and Y2
(reaction 3). When carrying out reactions 1, 2, and 3, a side formation of a brown
coating was found on the walls of the vessel, which turned out to be salt I, containing
3 elements in its composition (the mass fraction of the heaviest element is 57.20%).
This salt in its pure form has an orange-red color and is relatively stable (sublimes at
100°C), although it is also a very strong oxidizing agent. Salt I is formed during this
experiment due to a side reaction of a colorless gas X (one of the components of air)
with Y (reaction 4) and, from the point of view of stoichiometry, is the product of the
1:1 addition of X and Y, but this reaction is an oxidative restorative.
The possibility of obtaining I prompted the researchers to think about the

possibility of carrying out a similar reaction to obtain “salt II” (which is also
eight
should contain 3 elements, and the mass fraction of the heaviest of them should be 44.30%) when
replacing X with a colorless heavy gas A (“reaction 5”). The reaction between these substances
really took place, solid products were obtained containing the intransitive element Z
(this, in fact, marked the beginning of the chemistry of this element and dispelled many myths that
existed around the element Z and its analogues).
Soon , it was possible to synthesize binary substances B, C , and D from A , the mass
fractions of the lighter element in which are 22.4%, 36.7%, and 46.5%, respectively, using the same
reagent under different conditions (reactions 6–8). The existence and relative stability of these
substances made it possible to significantly expand the concept of the chemical bond.
After some time, it turned out that in the course of the reaction of A and Y , “salt II” is not
formed, but a complex mixture of products is formed, one of which is salt III (reaction 9), which can
be formally considered from the point of view of oxidation states as a product of the complexation
reaction B and Y1, and from the point of view of element ratios, as a product of the addition of A and
Y in a ratio of 1:2.
C and D react with water; in the case of C , the products containing Z are A and E (the
proportion of Z is 73.23% in the anhydrous substance) (reaction 10), and in the case of D ,
only E (reaction 11), which is relatively stable in aqueous solution, but highly explosive in anhydrous
form. Solution E, if it is carefully treated with sodium hydroxide, gives a monosubstituted salt F
(reaction 12), which decomposes in a concentrated alkaline solution with evolution of gas A and the
formation of an average salt G, which contains the element Z in the maximum degree of oxidation
(mass fraction Z 41.13%) (reaction 13). Treatment of the barium analogue of salt G with concentrated
sulfuric acid at negative temperatures leads to the formation of a light yellow explosive gas H
(reaction 14).
1. Decipher all unknown substances if mass fractions are indicated

elements - confirm the composition by calculation.
2. Write the equations for all the indicated reactions
3. Indicate the oxidation states of elements in salt I
4. Indicate the geometry of B, C and D. Explain why these compounds greatly enriched the
understanding of the chemical bond.
5. Which parameter, important for the reaction with Y, is close to ha
call A and X?
9
Task 8 (grades 9, 10, 11)

"Chemical Dinosaur"
The existence of the element X was predicted by D. I. Mendeleev on the basis of
the Periodic Law. For the first time, X was obtained artificially by irradiating a radioactive
isotope of element Z with deuterium nuclei. In this case, in addition to X , one neutron is
produced during each transformation event. Later, careful analysis of ores Z made it
possible to detect X in the amount of 10–14–10–10 g /kg of ore. Compounds X are
currently mainly used in medicine as a source of gamma radiation in the diagnosis of
brain tumors and bone tissue pathology, as well as as powerful anticorrosion agents.
agents.
XeF6 XeF6 KOH HCl

J I -M A F KI G
NO KCl, HCl (end),

L B E 100°ÿ, 20 hours
H
X
1)THF, t ÿC
D C 2) -20ÿC
K
The letter X in the scheme of transformations denotes a silver-white simple ve

the entity of the corresponding element.
At 450°C in a flow of dry oxygen, X is oxidized to form A, which crystallizes from
the gas phase in the form of light yellow crystals that are readily soluble in water; the
mass fraction of X in A is 63.85%. X reacts with fluorine in a closed nickel vessel at
400°C to form B. When X reacts with chlorine in sealed ampoules, C and D can form
depending on the amount of chlorine. Thus, in excess chlorine, at the molar ratio Cl2 : X
= 6, C is formed (the mass fraction of X is 41.09%). To obtain D , 0.10 g of Cl2 is frozen
into an ampoule and 0.14 g of X is placed there, after which the ampoule is vacuum
soldered, soldered and heated for several hours. When ammonia

is added to a concentrated aqueous solution A , a white crystalline precipitate of
salt E precipitates, the reduction of which usually gives pure X. When A reacts with a
solution of potassium hydroxide, F is formed.
When E is boiled for a long time in the presence of potassium chloride in

concentrated hydrochloric acid, yellow H is formed .
10
According to another method for obtaining H, 0.74 g of potassium iodide is added to a

solution of 0.3 g of F in 25 ml of 11.3 M HCl solution. The solution immediately turns red and
the red salt G begins to crystallize . When G is recrystallized from concentrated hydrochloric
acid, H crystallizes.
When 0.1332 g of A is reacted with 0.3164 g of XeF6 in anhydrous HF, yellow I is
precipitated . If 0.5273 g of XeF6 is added to the same amount of A , the precipitate begins to
form, but then dissolves due to the formation of the ionic compound J, which is soluble in HF.
Substance C has a polymeric structure; therefore, it dissolves only in boiling anhydrous

THF for 2 hours, after which the solution is cooled to -20ÿÿ and yellow K is separated after 12
hours. To obtain L , 0.2427 g of V and 0.13 g NO, then the vessel is closed, and its temperature
is raised to room temperature, after an hour the vessel is cooled, and the excess NO is
evaporated in vacuum at a temperature of ÿ78 °ÿ, leaving 0.2769 g of yellow salt L. Additional
information:
In solid compounds B, C, G, H, I, J, K, L , the coordination number

(c.h.)* X is equal to 6. In compounds A, E, F c.h. = 4, and in D c.h. = 5.
Substance B has a molecular structure in both gas and solid phases.
Compounds H and G are isostructural† , and 0.0787 g H can be obtained from 0.1000
g G ( 75% yield) .
schee X, having in its composition 7.17% oxygen.

All starting materials are taken in stoichiometric amounts, unless
indicated
otherwise. Tasks:
1. Determine the element X. Write the equation for a nuclear fusion reaction
X. Define element Z.
2. How many alpha and beta decays must the 235U nucleus undergo in a nuclear reactor
in order to form the most stable X isotope? The same isotope X can also be formed when the
235U nucleus divides into two nuclei, and one neutron is also released, write down the equation.
3. Determine the composition of substances A–M. Support your answer with calculations.
Write the equations for all the reactions shown in the diagram (14 equations).
4. Draw the possible isomers of substance K.
*
The coordination number is the number of nearest neighbors in the crystal structure
† Have different composition but same crystal structures
eleven
12
Organic chemistry
Task 1
Steroid hormones regulate vital processes in animals and humans. A
common feature of all steroids is the presence of a system of four condensed
rings, three of which are six-membered and one five-membered, as shown in the
figure. For example, one of the most important female sex hormones is
progesterone (Z), which plays an important role in pregnancy. The first complete
synthesis, including 15 stages, of progesterone was published by W. Johnson in
1971. This synthesis can be divided into two parts. The product of the first is (E)-4-
methyldec-3-en-8-inal (X), which was further used in the synthesis of progesterone.
Tasks:
1. Give the structural formulas of compounds A–C, taking into account that
the transformation of A into B is a stepwise process that includes the Claisen
rearrangement (the so-called Johnson-Claisen rearrangement).
The second part of the synthesis is shown in the diagram below:
2. Give the structural formulas of compounds D–L, taking into account that G
contains two double bonds of the trans configuration.
Note: Me = methyl; Et = ethyl; Bu = butyl; Ph=phenyl;
thirteen
Task 2
Wormwood huddles at the fences,
On the roofs of baths and cellars,
Blooms on slopes
In the ditches, near the poles...
("Wormwood", Timofey Belozerov)
Artemisinin (Z) was discovered in 1971 by Chinese pharmacologist Tu Youyou while
searching for a cure for malaria during the Vietnam War. Based on the recipe described in a
book written in 340 AD. e., she isolated Z from sagebrush annual. In 1973, she received
dihydroartemisinin (A), which has a higher antimalarial activity than Z, and then other active
derivatives. For these studies, she was awarded the Nobel Prize in Medicine and Physiology in
2015. Currently, artemisinin and its derivatives (artemether, artesunate) are the standard
treatment for malaria worldwide. Compound Z has been found to have antitumor activity in the
past few years and is now being tested as an anti-cancer drug.
ka.
The high cost and limited bioavailability of Z led to the need to search for synthetic
methods for its production, which would increase the production volume of the drug. Below is
a scheme for obtaining Z from artemisinic acid, the content of which in wormwood is
dock exceeds the amount of artemisinin itself.
14
Tasks:
1. Decipher the transformation scheme and write the formulas of products B–E.
Compound B can also be obtained from available natural
substances - isopulegol and citronellal, which are found in essential oils.
2. Decipher the transformation scheme and write the formulas for the G–S products.
Task 3
“In organic synthesis one can find both challenge and daring
adventure, and insight, and inspiration of art."
R. B. Woodward
"The country in which the storm brought Gulliver,
called Lilliputia"
J. Swift
October 2016 marks the 85th anniversary of the birth of Kenkichi Sonoga Shira,
who in 1975 described the cross-coupling reaction between aryl halide
dams and alkynes, proceeding under very mild conditions in the presence of com
transition metal plex.
As a catalyst, Sonogashira used the Y complex obtained from the commercially

available Z salt and triphenylphosphine. Salt Z is obtained by co-crystallization from an
aqueous solution of two halides Q and R. From-
15
It is known that the content of the transition metal in Q, Z , and Y is 60.01%, 36.17%,
and 15.16%, respectively.
Tasks:
1. Determine the halides Q and R, the salt Z and the composition of the complex Y. Suggest
those structural formula of the complex Y.
The Sonogashira reaction has firmly entered the arsenal of synthetic chemists
2
as a reliable and general method for creating sp in ka -sp carbon-carbon bonds. V
In 2003, chemists from Texas published a paper in which they described the preparation
of "nanoputians" (NanoPutians), "humanoid" organic molecules "growth in volume" of
about 2 nm. Thus, in the given scheme for the synthesis of the "nanochild", the
Sonogashira reaction is used 4 times.
2. Write the structural formulas of compounds A–L and the “nanochild” (N).
Task 4
In 1992, a number of compounds of similar structure, called decarestrictins, were
isolated from the mold fungus Penicillium Simplicissimum . Currently, 20 decarestrictins
are known, which have different letter designations from A to O (for example,
"decarestrictin A1"). Many of these compounds are of considerable interest due to their
ability to inhibit the synthesis of cholesterol, therefore, in recent years, significant efforts
have been made to develop methods for the synthesis of decarestrictins. So, in 2015,
according to the scheme presented below, the first synthesis of decarestrictin G, a
macrocyclic lactone with
tenfold cycle.
sixteen
Tasks:
1. Give the structural formulas of compounds A–E and decarestrictin G
(no indication of stereochemistry). Note that: a) the OsO4/NMO system is used as an
efficient and highly selective reagent used in place of the neutral aqueous KMnO4 solution;
b) N,N'-dicyclohexylcarbodimide (Cy–
N=C=N–Cy) facilitates condensation reactions by binding a water molecule. Write the
structure of the resulting product.
Unlike most other decarestrictins, decarestrictin L is not a lactone and does not
contain a ten-membered ring. However, its high biological activity has led to great interest
in it from synthetic chemists. The scheme shows the first synthesis of decarestrictin L,
carried out back in 1993.
2. Write the structural formulas of compounds F–P and decarestrictin L, if it is known

that: a) only one epoxy cycle is affected in the first stage, and the reaction proceeds
according to a mechanism similar to that of SN2; b) compound L contains two cycles.
17
Chemistry and Life

Task 1
“In every big business, you always have to leave some

part to chance”
Napoleon ©
In the entire history of mankind, there was no medicine that would save as many lives as
penicillin. We owe the discovery of this antibiotic to the Scottish microbiologist Alexander Fleming, or
rather, to his interesting habit. Unlike his neat colleagues, Fleming put off washing laboratory glassware
until the last moment, and only when several dozen Petri dishes accumulated on the table did the
scientist reluctantly take up such an unpleasant job.
And then one day, while studying Staphylococcus aureus, Fleming discovered mold in one of the
cups. To the scientist's surprise, this mold dissolved the colony of bacteria that lived in the cup, leaving
only droplets of some strange dew-like liquid in its place. A few years later, the biochemists Chain and
Flory managed to isolate the unstable substance in its pure form. After establishing the structure of
penicillin, its first laboratory synthesis was carried out.
Tasks:
1. Decipher the structural formulas of compounds A–F and penicillin G,
if it is known that:
1) The central part of penicillins responsible for biological activity is the condensed bicyclic ÿ-
lactam-thiazolidine
system:
eighteen
2) Compounds A, B and D are bicyclic.

3) The biosynthesis of penicillin G proceeds in three stages from L-cysteine, D-
valine and L-ÿ-amino-adipic acid (its ÿ-carboxyl group is involved in the reaction),
through the formation of the so-called ACV-tripeptide and isopenicillin N.
2. Draw the structure of the ACV tripeptide and mark all chiral centers
in the structure of penicillin G.
Some time after the discovery of penicillin and its active use in clinical practice,
people began to notice a decrease in the effectiveness of the drug. It turned out that
many bacteria learned to synthesize special ÿ-lactamase enzymes that made their
hosts resistant to penicillin. In the active center of ÿ-lactamases, the following occurs
reaction:
HX
- amino acid residue in the active site of ÿ-lactamase.
3. X could be an atom of which element ?
But humanity was not going to admit its defeat and began to look for a way out.
Soon it was found, and new substances appeared - ÿ-lactamase inhibitors.
Structurally, they are similar to penicillins, but, unlike them, ÿ-lactamase inhibitors
form a covalent compound with the enzyme that is not subject to hydrolysis, thereby
preventing the interaction of the enzyme with the antibiotic. One of these inhibitors is
clavulanic acid, which is a metabolite of another mold that synthesizes it.
nineteen
from arginine and glyceraldehyde-3-phosphate according to the following scheme:
Enzymes (labeled above the arrows):

1) N2 -(2-carboxyethyl)-arginine synthase - belongs to the family of
transferases, that is, it catalyzes the transfer of small groups; 2) ÿ-lactam
synthetase catalyzes the formation of a carbon-nitrogen bond with the consumption
of ATP; 3) clavamine synthase - belongs to the family of monooxidases, that is, it
adds one oxygen atom (to the carbon atom adjacent to the carboxyl group, which
in the case of unstable compounds can lead to subsequent elimination of water);
4) amidinohydrolase, belongs to the class of enzymes that catalyze hydrolysis;
5) an enzyme catalyzing oxidative deamination; 6) dehydrogenase, an enzyme
that catalyzes the reduction reaction.
Note: the formation of products IV and V proceeds in two stages, the first of
which is oxidation; substances IV–VI are bicyclic. ATP - adenosine triphosphate,
AMP - adenosine monophosphate, PPi - pyrophosphate
4. Identify compounds I–VI and draw their structural formulas.
Task 2
prebiotic chemistry
Since Miller's experiments in obtaining vital organic compounds from the
"primordial soup", other chemical reactions have been discovered that can
produce organic matter under the conditions of the ancient Earth. One of the
intensively studied such reactions is Butlerov's formosa reaction, discovered
twenty
melted back in 1865. In this reaction, an aqueous solution of formaldehyde with the
addition of alkaline earth metal ions (Ca, Mg) with slight heating
turns into a complex mixture of sugars.
Tasks:
1. Write the scheme of Butlerov's formosa reaction up to and including 5-carbon
sugars. (It's not the configuration of the sugar that matters, but the presence of a 5-carbon chain)
In the Butlerov reaction, a mixture of complex sugars is obtained, in which there
are also molecules that are toxic to cells. However, in recent years, several ways
have been discovered to selectively accumulate individual sugars, precisely those
that are needed for biochemistry. For example, it was found that the presence of
SiO2 in the reaction mixture leads to the selective accumulation of exactly five
and six-carbon sugars.
Let's move on to nucleic acids. As is known, in order for a nitrogenous base to
be able to participate in RNA synthesis, it must first combine with sugar and
phosphate. Back in the 1960s, it was shown that upon ultraviolet irradiation of a
solution of adenine, ribose, and phosphates, adenine first forms a bond with ribose,
and then adds three phosphate groups in succession, turning into ATP.
However, this method for the synthesis of activated nucleotides is not suitable
for other nitrogenous bases. Guanine attaches ribose upon irradiation, but practically
does not react with phosphate. Pyrimidines do not react with ribose either. Therefore,
a very important milestone in the study of prebiogenic syntheses was the work of
Sunderland et al. published in 2009.
The authors mixed cyanoacetylene (7), cyanamide (8), glyceraldehyde (9),
glycoaldehyde (10) and phosphate in water and heated. It would seem that a huge
amount of by-products should be obtained in this mixture. But the experiment
disproved this assumption. This synthesis is striking in its elegance: the by-products
of some reactions here become catalysts for subsequent ones, the phosphate directs
the reactions in the right direction long before entering the final product, and the key
intermediate (11, contains the oxazoline cycle) is capable of self-purification and
accumulation in high concentrations due to its high volatility - it evaporates well from
aqueous solutions at slightly elevated temperatures and condenses during the night
frosts.
2. Decipher the scheme of chemical transformations below:
21
C3H6O3
O Oh 9
40ÿC
HO Oh C6H10N2O4
C2H4O2 16 hours
Oh 10 -H2O 12
C3H4N2O
NaOH/H2O, 60ÿC
+H2O eleven
C H4N2O CH2N2
-H2O 6 eight
C5H10O5 C4H5N3O
4 3 +H2O
C3H3NO C3HN
5 7 Phosphate buffer
-H2O pH=6.5
O 16 hours
C9H13N3O5 HO P Oh C9H11N3O4
-
2 O thirteen
-2H2O
-H2O
After that, it was also found that L-proline selectively binds to L-9, which leads
to the accumulation of D-9 and, accordingly, stereoselective synthesis of the resulting
ribonucleotide.
Later, work appeared on the possible prebiotic synthesis of DNA. The key point
of these works was the use of sulfur-containing compounds to obtain 2'-
deoxyribonucleotide.
3. Decipher the transformation scheme below:
Note that (14) is very similar to (10), (17) is an oligomerization product

(16) with the addition of one water molecule, (19) is formed from (18) with the
formation of a carbon-carbon bond, (19) and (19') are isomers, and in (19) there are
two cycles, in (19') - three cycles. Arrange in (19') the numbers of carbons that are
marked in the final compound.
22
Physical chemistry
Task 1
To establish the component composition, thermal stability intervals, purity of substances, and
kinetic parameters of decomposition reactions, such an analysis method as thermogravimetry (TG) is
used. In this method, the change in chemical and physical parameters is recorded as a function
temperature or time.
The figure shows a graph of the one hundred
I
A, B
change in mass (%) of a solid from -XA -XB

90 II CA
tempera CB
80
thermal decomposition of 100 g of A -YB -YA
V III
substances A and B with the formation 70 DA
D.B.
of final products EA and EB , respectively 60
-ZA -ZB
50
but.
40
A B EA , EB
o o
ÿrH on ÿrH on thirty
0 100 200 300 400 500 600 700 800 900

O
w , loss w , loss T, WITH
a kJ mas a kJ mas
G /youth sy, G /youth sy,
b % b %
I 37 a I 37.7 a +
1.2
II 35 19.2 II 35.0 18.9
II 177 30.1II 177 29.7
I I
At stage II of A decomposition at 500°C and normal atmospheric pressure, 43 L of YA is

released. ZA is absorbed by the Ba(OH)2 solution to form a white precipitate.
To determine the XA content in A, a 0.7373 g sample of A was dissolved in concentrated sulfuric

acid, the resulting solution was transferred into a 100 mL volumetric flask and made up to the mark with
distilled water . Titration of a 10.0 ml aliquot required 20.2 ml of a 0.01 M KMnO4 solution.
Tasks:
1. Based on thermogravimetry data, determine the substances CA, DA,
EA, XA, YA and ZA.
23
2. Determine substance A, write the equations of reactions occurring during

sample preparation and permanganatometric titration.
3. Install substances B, CB, DB, EB, XB, YB and ZB.
4. Write the reaction equations for all stages of thermal decomposition of B.
5. Determine ÿfH°298XB(kJ/mol) if it is known that
ÿfH°298(V) = ÿ1685 kJ/mol,
ÿfH°298(Yÿ) = ÿ111 kJ/mol,
ÿfH°298(EV) = ÿ635 kJ/mol,
ÿfH°298(Zÿ)= ÿ394 kJ/mol.
Task 2
"Breathing Crystals"
The adsorbent is adsorbed on
the adsorbent, turning into an adsorbate
In 1989, a new class of porous materials was discovered, the structure of which
is formed from transition metal cations linked together by bridging organic ligands.
Interest in such materials is due to the prospects for their practical application. Yes,
the material
DUT-49 (blue cubic crystals) exhibits the highest methane adsorption capacity of
currently known porous compounds.
The structure of DUT-49 is based on fragments A, where

two metal X atoms are connected via four carboxyl groups of
tetracarboxylic acid anions
L(COOÿ )4 (fragment A). Each fragment A is located at the A V
vertices of the octahedron connected to each other by means
of L (fragment B).
Tasks:
1. How many X atoms and L(COO- )4 fragments per fragment
b?
From B , a cubic unit cell DUT-49 (fragment C) is
formed, at the vertices and in the centers of the faces of
which there are B fragments connected with the help of L.
The density of DUT-49 is 0.310 g/cm3
WITH
, and the volume of the elementary
cells - 101 nm3 .
2. Calculate the number of fragments B in unit cell C.
3. Install metal X. Confirm your answer with a calculation. Accept that
24
ÿ(L(COOH)4) = 660.6 g/mol.

Physical adsorption is the concentration of a substance from a volume in the surface
layer of a material. Gas molecules D reversibly combine with active centers Z on the surface
of a porous sample:
,
where K is the adsorption equilibrium constant). The dependence of adsorption a on gas
pressure is described by the Langmuir equation:
Kp
aa
ÿ
max ,
one ÿ Kp
where amax is the maximum adsorption that takes place at very high pressure, when all
active sites Z are occupied by gas molecules. Adsorption data are widely used to establish
sample characteristics such as pore volume and specific surface area. Below is a table of
nitrogen (77 K) and methane (111 K) adsorption values on DUT-49 depending on their
pressures (p0 is the pressure of saturated gas vapors).
p/ 0.05 0.10 0.15 0.20 0.25

p0 ÿ(N2), mmol/g material 3.1 5.9 8.6 11.0 13.3
a(CH4), mmol/g material 7.4 13.5 10.8 12.9 14.7
4. In what coordinates does the dependence a(p) have a linear form? Using these
coordinates, determine amax for nitrogen and calculate the total pore volume per gram of
DUT-49 (cm3 /g) and its specific surface area (m2 /g).
The values of methane adsorption on DUT-49 were initially taken by scientists as an
instrumental error in the experiment. However, later they managed to establish the true
cause of this unusual phenomenon.
5. What surprised the scientists? What adsorption values in the saturation region
were expected by the researchers? Suggest a reasonable explanation for the observed
phenomenon. Support your answer with a calculation. Additionally, it is known that, in
the case of methane adsorption, amax = 31.9 mmol/g material.
Reference data required to solve the problem:
, ,
, ,
, .
25
Task 3
The adsorption of gases on a solid surface in some cases can be described
as a reversible chemical reaction
,
where A is a gas molecule, Z is a free active center of a solid surface, AZ is an active
surface center occupied by a molecule A , and K is the adsorption equilibrium constant.
In the Langmuir approximations, it is assumed that the filling occurs according to

surface with only one layer of particles, all surface centers are equivalent, and there
are no interactions between adsorbed particles of the same type.
Tasks:
1. Determine the signs of the functions ÿrG, ÿrH , and ÿrS for spontaneous
adsorption. What factor - enthalpy or entropy - determines the course of this process?
Briefly explain.
2. How does temperature change affect the adsorption equilibrium? Justify the
answer. 3. Knowing the gas pressure and the equilibrium constant of adsorption, derive
an expression for the equilibrium degree of coverage ÿ of the surface (the fraction
of the filled surface) with molecules A for the given adsorption model. Use the concept
of surface concentration to calculate free and occupied
active centers of the surface.

4. The process of catalytic oxidation of carbon monoxide can be simplified
but is represented by a combination of three stages:
Knowing the total concentration of catalyst active sites [Z]0, gas pressures, and
assuming that gas adsorption obeys Langmuir approximations, derive an expression
for the rate of the presented catalytic reaction ( CO2 production rate). Consider that
equilibria are established quickly. What orders in O2 and CO does the reaction have at
their low pressures?
5. The rate of this catalytic reaction can also be written as V = keffÿZCOÿZO,
where ÿZCO and ÿZO are the degrees of occupation of the active centers of the catalyst
surface by CO molecules and O atoms, respectively.
Using the data of point 4, derive an expression for keff in this entry.
26
6. Velcro for flies works until a full layer of adherent flies forms on it. Is it possible to consider
the processes in the “fly-flypaper” system as an analogue of Langmuir adsorption? Justify the answer.
Task 4
Molecular tweezers are chemical compounds capable of gripping

to form other smaller molecules by binding to them from two opposite sides. One of the many
examples of compounds of this kind are aminoboranes with spatially closely spaced functional
groups, which are capable of reversibly binding a water molecule.
sort by reaction
where A is aminoborane.
The structural formula of one of the substances of such type
1-(2-borylphenyl)-2,2,6,6-tetramethylpiperidine (BorylCAT) is
shown in the figure on the right.
Tasks:
1. Explain how aminoborane
BorylCAT can bind a hydrogen molecule.
Thermodynamics and kinetics of the BorylCAT reaction with hydrogen
were studied in solution in CD2Cl2 at temperatures from 0 to 30°C by NMR spectroscopy. The table
lists the obtained values of the equilibrium constants Kc for the forward reaction (i.e., the reaction of
hydrogen binding) and the rate constants k2 for the reverse reaction of dissociation of the AH2
complex.
T, °C 0 10 twenty thirty
Kc, M–1 110 50 thirty 10
k2, s–1 0.001 0.004 0.011 0.076

2. Without calculations, determine the signs of enthalpy (ÿrH°) and entropy (ÿrS°) for the
reaction of hydrogen bonding with BorylCAT aminoborane. Justify your answer.
3. Find the values of ÿrH° and ÿrS° for the reaction of hydrogen bonding with aminoborane
BorylCAT, assuming these values to be constant in the ex
temperature range.
4. Determine the activation energy for the dissociation of the BorylCAT complex with
hydrogen.
27
Hydrogen was bubbled into a solution of BorylCAT in CD2Cl2 for 1 second at 0°C. Since
under these conditions BorylCAT is in a large excess with respect to hydrogen, we can assume
that the time dependence of [H2] is described by the following formula:
,
where [H2]ÿ is the equilibrium concentration of hydrogen.
5. Estimate how long after the start of bubbling the concentration of free hydrogen in the
solution will differ from the equilibrium one under these conditions by no more than 1%.
Two identical ampoules for NMR spectroscopy withstanding elevated pressures were
filled with 0.50 ml of a solution of BorylCAT in CD2Cl2 with a concentration of 0.05 M. Argon
was passed through both solutions at atmospheric pressure for a minute. Then, hydrogen was
bubbling through the solution in the first ampoule using a thin capillary reaching the bottom of
the ampoule in the flow mode at a pressure of 5.0 bar until thermodynamic equilibrium was
established. In the case of the second ampoule, hydrogen was quickly let into the upper part of
the ampoule, initially filled with argon, until the total pressure in the ampoule reached 5.0 bar
(the amount of hydrogen dissolved during this time is negligibly small). Then the access of
hydrogen was blocked, and the ampoule was left until
establishment of thermodynamic equilibrium.

6. For solutions in both ampoules, calculate the mole fraction of hydrogen ÿ, bound in a
complex with BorylCAT, from the total amount of hydrogen in the solution. The experiments
were carried out at 0 °C. Consider that the ampoules have the shape of a cylinder with an outer
diameter of 5.0 mm, a wall thickness of 0.77 mm, and a height of 20.3 cm. The dependence of
hydrogen solubility on pressure obeys Henry's law (see reference data).
Reference data:
The dependence of the equilibrium constant on temperature:
Arrhenius equation: Henry's

,
law: where C is the gas concentration in the solution, H is the Henry constant, P is the
partial gas pressure over the solution.
Henry constant for H2 at 0 °C: H = 2.10 10–3 mol l–1 bar–1 .
1 bar = 105 Pa.
28
Task 5
The phenomenon of fluorescence was discovered by Stokes when he observed that
certain substances glow blue when irradiated with invisible ultraviolet radiation. In the
general case, when a substance absorbs light with a certain wavelength ÿ1 , light with a
different wavelength ÿ2 can be emitted. The difference between the wavelengths can be
due to the fact that a molecule or crystal lattice that has passed into an excited electronic
state returns to an unexcited state, but not to zero, but to one of the excited vibrational
levels. It is known that the energy of the nth vibrational ÿ
ÿ one
the level is described by formula 2 E n ÿÿ of

ÿ h ÿÿ where ÿ is the oscillation frequency.
n
ÿ ÿ,
Tasks:
1. Express the emission wavelength ÿ2 in terms of the excitation wavelength ÿ1, the
number of the vibrational level n to which the molecule returns, and the vibration frequency
ÿ.
(Consider that before the excitation, as well as in the excited state of the mole
kula is at zero vibrational levels).
Substances often fluoresce while simultaneously emitting light of different
wavelengths. In this case, the frequency difference of the emitted light for neighboring poppy
intensity simumas in the spectrum is the same.
2. Express this difference in terms of the same variables as in step 1.
By measuring the intensity of fluorescence, very low concentrations of fluorescent
molecules can be determined, as well as studying the chemical
sky processes with their participation.
Protein molecules are capable of fluorescence due to the presence of tryptophan
and tyrosine in their amino acid sequence. During the formation of complexes of such
proteins with low molecular weight compounds, fluorescence
may disappear.
Albumin protein binds to ascorbic acid (L) in a molar ratio of 1 : 1. Solutions were
prepared with the same protein concentration of 1.0ÿ10ÿ6 M and different concentrations
of the ligand. The measured values of fluorescence intensity F (which is proportional to
the concentration of unbound protein) are given in the table. Excitation intensity
does not change during the experiment.
29
cL / M F, rel. units cL / M F, rel. units

923 4.0ÿ10ÿ4 126
0 1.0ÿ10ÿ4 352 5.0ÿ10ÿ4 101
2.0ÿ10ÿ4 218 6.0ÿ10ÿ4 84
3.0ÿ10ÿ4 160
3. Find the value of the stability constant of the complex of albumin with ascorbic acid.
The decrease in the fluorescence intensity can also be due to the fact that the excited state (P*) upon
collision with another molecule (L) passes into the unexcited state (P) without light emission. Let the rate
constant of this process be equal to k1, while the rate constant of the radiative transition is equal to k2:
PL* ÿ ÿÿÿ ÿ k one
PL
P * ÿÿÿk ÿ P h
2
ÿ
4. Show that in the case of fluorescence quenching according to the above mechanism and the
absence of complex formation between P and L, the dependence of the fluorescence intensity F on the
concentration L (cL) at a constant concentration
F0
tion P is expressed by the equation
ÿ
Kc' L 1 ÿ , where F0 is the fluoresce intensity
F
cL = 0. Express K' in terms of k1 and k2.
Some molecules are capable of simultaneously quenching protein fluorescence both by binding and
by collisions with molecules in an excited state. The binding of albumin to caffeine also occurs in a molar
ratio of 1 : 1. Solutions were prepared with the same protein concentration of 5ÿ10ÿ6 M and different
concentrations of caffeine. The measured values of the fluorescence intensity (which is proportional to the
concentration of unbound protein) are given in the table.
cL / M F, rel. units 953 cL / M F, rel. units

8.0ÿ10ÿ4 115
0 2.0ÿ10ÿ4 399 1.0ÿ10ÿ3 86
4.0ÿ10ÿ4 231 1.2ÿ10ÿ3 68
6.0ÿ10ÿ4 158
5. Find the possible values of the stability constant of the albumin-caffeine complex.
thirty

Inorganic Chemistry 2: Table of Contents

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Inorganic Chemistry 2: Table of Contents

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Task 1 (Grade 9) ............................................... ................................. 2

Task 2 (Grade 9) .............................................. ................................. 3

Task 3 (Grade 9) ............................................... ................................. 3

Task 4 (Grade 9) .............................................. .................................. 4

Task 5 (grades 9, 10) .......................................... ............................ 5

Task 6 (grades 9, 10) .......................................... ................................... 7

Task 7 (grades 9, 10, 11) .............................................. ........................ eight

Task 8 (grades 9, 10, 11) .............................................. ...................... 10

Organic chemistry thirteen

Task 1 ................................................. ......................................... thirteen

Task 2 ................................................. ......................................... 14

Task 3 ................................................. ......................................... 15

Task 4 ................................................. ......................................... sixteen

Chemistry and Life eighteen

Task 1 ................................................. ......................................... eighteen

Task 2 ................................................. ......................................... twenty

Task 1 ................................................. ......................................... 23

Task 2 ................................................. ......................................... 24

Task 3 ................................................. ......................................... 26

Task 4 .................................................. ............................................... 27

Task 5 .................................................. ............................................... 29

© TsPMK Higher School of Chemistry

© TsPMK Higher School of Chemistry

The solution initially acquired a brown color, which

When calculating, assume that the current outputs are 100%.

© TsPMK Higher School of Chemistry

A solution of salt B, which also contained an excess of sodium hypochlorite , was

* when adding ethyl alcohol, the solubility of the substance G decreases

© TsPMK Higher School of Chemistry

a precipitate of crystalline hydrate G precipitated from the

occurs as the oxide M.

© TsPMK Higher School of Chemistry

Task 5 (grades 9, 10)

© TsPMK Higher School of Chemistry

All encrypted substances contain the element X. A, C – M are crystalline substances,

B green (in reflected light), dark red (in 49.55

Bluish Violet J White 13.03

KL Light pink Red-violet M Upon slight 30.69

When 0.1 mol of substance F is dissolved in water, a green solution of substance E

© TsPMK Higher School of Chemistry

Task 6 (grades 9, 10)

Metal X dissolves in hydrochloric acid, forming a violet solution of substance D.

When C is added to a solution of sodium cyclopentadienyl in tetrahydrofuran (THF),

© TsPMK Higher School of Chemistry

at 25°C. Pyrophoric crystals J are obtained by recrystallization from benzene.

Quantity ÿ( ÿ), % Color Quantity ÿ( ÿ), % Color ÿ 66.6 violet H

Task 7 (grades 9, 10, 11)

The possibility of obtaining I prompted the researchers to think about the

© TsPMK Higher School of Chemistry

1. Decipher all unknown substances if mass fractions are indicated

© TsPMK Higher School of Chemistry

Task 8 (grades 9, 10, 11)

XeF6 XeF6 KOH HCl

NO KCl, HCl (end),

The letter X in the scheme of transformations denotes a silver-white simple ve

soldered, soldered and heated for several hours. When ammonia

When E is boiled for a long time in the presence of potassium chloride in

© TsPMK Higher School of Chemistry

According to another method for obtaining H, 0.74 g of potassium iodide is added to a

Substance C has a polymeric structure; therefore, it dissolves only in boiling anhydrous

In solid compounds B, C, G, H, I, J, K, L , the coordination number

schee X, having in its composition 7.17% oxygen.