Download Questions and problems for module control

Questions and problems for module control
Module control 1.
1.
What kind of conjugation is there in the following compound? Using the arrows of inductive and resonance
H
H
H
N а) π-π- conjugation; b) р-πeffects show the situation of electron density in molecule H2C C C C C
conjugation; c) σ-π- conjugation; d) σ-р- conjugation; e) р-р- conjugation; f) no conjugation
CH 3
2.
Dispose
3)
H 3C
the
H2
C
H
C
free
CH 3
radicals
as
their
stability
grows:
1)
H3C
C
CH 3
2)
H2
C
H2
C
CH 2
,
а) 1,2,3; b) 3,1,2; c) 2,3,1; d) 1,3,2 ; e) 2,1,3; f) 3,2,1.
. Explain.
COOH
H
3.
,
H 3C
OH
COOH
HO
H
CH 3
CH 3
What kind of isomerism is there in the following pair of compounds
а)
chain
isomerism; b) position isomerism; c) metamerism; d) tautomerism; e) functional group isomerism;
f) enantiomerism; g) geometrical isomerism; h) conformational isomerism.
Cl
H3C
C
CH3 O
CH
C
H
Cl
4. Give the name to the following compound using the IUPAC nomenclature:
5. What products can be created as a result of monochlorination of butane under the light. Arrange them
in order of increasing of creation possibility. Explain. Write the reaction equations and conditions.
а) 2-chlorbutane, 3-chlorbutane, 1- chlorbutane; b) 1-chlorbutane, 2-chlorbutane; c) 2-methyl-2chlorpropane, 2-methyl-1- chlorpropane, 1- chlorbutane; d) 2- methyl -1- chlorpropane, 2- methyl -2chlorpropane;
6. Hydrocarbon С5Н12 has three products of monochlorination. What is the structure of its hydrocarbon?
Write the equation of monochlorination and conditions. а) neopentane; b) isopentane; с) 2,2dimethylpropane; d) 2-methylbutane;
Write the reaction of addition of HBr to 4-methylhex-1-ene with peroxides presence. What is the
7.
mechanism of this reaction?
Choose the right way of synthesis. Write the equations.
8.
СН СН  Вr
 NaNН 2
 AlkKOH
А) ethyne 

( А)  3  2 
( B)   
 bu tan 2  on
2
СН СН  Вr
 Na
 Н 2О ( Hg )
В) ethyne 
( А) 

( B) 3 2 
 bu tan 2  on ;
СН СН  Вr
 NaН
 AlkKOH
С) ethyne 

( А)  3  2 
( B)   
 bu tan  2  on ;
2
СН СН 2  Вr
 NaNН 2
 Н 2О ( Hg )
D) ethyne 

( А) 3 

( В) 
 
 bu tan 2  on .
9. What are the products of ozonolisys of 1,2,3,4 -tetramethylbenzene (1 mole of toluene). Write the
equations. A) 0,5 mole of glioxal, 1 mole of methylglioxal, 1,5 mole of diacetyl; B) 1 mole of glioxal, 1
mole of methylglioxal; 1 mole of diacetyl; C) 0,5 mole of glioxal, 2 mole of methylglioxal, 0,5 mole of
diacetyl; D) 1 mole of diacetyl, 2 mole of methylglioxal.
COOH
10. Receive the dyeing compound from azo- and Cl
diazocomponent. Give the names of the compounds.
11. Find out the structure of aromatic compound using the
empirical formula and the products of chemical reactions:
С3Н9N , while the reaction with HCl salt is created, doesn’t
react with HNO2. Write the equations.
12. Receive p-methylbenzonitryl from nitrobenzene.
N
N(CH 3)2
N
1.
Module 2.
Choose the correct scheme of synthesis of trans-cyclopentandiol-1,2. Write the equations.
2
2
  A 

 B    С
A) cyclopenta ne 
Cl ( світло)
H O
[ O ] Vagner' s

В)
O ] Vagner' s
3O
2O
cyclopenta ne H
 A H

 B [
 С
C)
світло)
( alc)
O ] Vagner' s
cyclopenta ne Cl
2 (
 A KOH

 B [
  С
D)
cyclopenta ne    А    В   С
[ O ] Vagner' s
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
Cl 2 ( світло)
KOH ( alc)
Find out the structure of the compound using the empirical formula and the products of chemical reactions: С8Н8О, while the
reaction with hydroxylamine, sodium bisulphide and phenylhydrazine, crystal precipitates are created, while oxidation,
isophtalic (benzene-1,3-dicarboxilic) acid is created. Give the name to this compound. Write the equations. A) pmethylbenzaldehyde; B) m-methylbenzaldehyde; C) phenylmethanal; D) acetophenone.
What compounds can be used to receive the compound while the aldol-crotonic condensation
O
C C C C C
H H
H H
.Write the equations and the names of carbonil component (first) and methylen component
(second): A) benzaldehyde and propanal; B) acetone and benzaldehyde; C) phenylethanal and ethanal; D) benzaldehyde and
acetone.
Give the name to the following compound using IUPAC nomenclature. A) methyl butanoate; B) butyl
methanoate; C) 3-methoxybutanoic acid; D) β-methoxybutanoic acid.
Write the structural formulas of the following substances, arrange them according to increasing of the ability to take place in the
reactions of nucleophilic substitution, explain: 1) N-phenylisipropanamide, 2) isopropanoyl chloride, 3) isopropanamide. A) 1,
2, 3; B) 1, 3, 2; C) 2, 1, 3; D) 2, 3, 1; E) 3, 1, 2; F) 3, 2, 1.
Write the schemes of synthesis starting from acetoacetic ester with using 1 mol of acetoacetic ester, 2 mol of chloropropane
(cleavage with using of con. bases solution). Give the name to synthesis products. A) pentanoic acid; B) hexanone-2; C) 3methylhexanone-2; D) 2-prpylpentanoic acid
For the mixture of Glycine, Phenylalanine, and Serine indicated at pH = 6.0, predict the direction of migration of each
component (toward anode or cathode) and relative rate of migration if values of the isoelectric points are 6.0, 5.5, and 5,7
respectively A) toward anode: Phe>Ser, toward cathode: none; B) toward anode: none, toward cathode: Gly>Phe; C) toward
anode: Phe, toward cathode: Gly; D) toward anode: Phe>Ser> Gly, toward cathode: none.
Find out the structure of the compound С6Н13NO2, while heating six-membered heterocyclic compound with one nitrogen atom
С6Н11NO is created. Write the equations of С6Н13NO2 with HNO2, HCl, and NaOH. A) 2-amino isohexanoic acid; B) 2-amino
hexanoic acid; C) 5-amino hexanoic acid; D) 4-amino isohexanoic acid;
Write all steps required for the syntesis of Glu-Cys from amino acids by solid-phase syntesis. Give the names to N- та Сterminal amino acids
A) 1 - protection of Glu NH2-group
using methanol, 2 - protection of Cys COOH-group using BOS, 3 – coupling of two protected amino acids using DCC, 4 removing of BOS by acid treatment, 5 - removing of methyl ester by basic hydrolysis;
B) 1 - protection of Glu NH2-group using BOS, 2 - protection of Cys COOH-group using chloromethylated polystyrene, 3 –
coupling of two protected amino acids using DCC, 4 - removing of BOS by acid treatment, 5 - removing of chloromethylated
polystyrene;
C) 1 - protection of Glu NH2-group using BOS, 2 protection of Cys COOH-group using methanol, 3 – coupling of two protected amino acids using DCC, 4 - removing of BOS by
acid treatment, 5 - removing of methyl ester by basic hydrolysis;
D) 1 - protection of Cys NH2-group using BOS, 2 - protection of Glu COOH-group using chloromethylated polystyrene, 3 –
coupling of two protected amino acids using DCC, 4 - removing of BOS by acid treatment, 5 - removing of chloromethylated
polystyrene;
What carbohydrate is created while the Wohl degradation of C-3 epimer of L-Galactose? Write the equation. A) D-Ribose; B) LXylose; C) L-Arabinose; D) L- Fructose.
What is the cause the aniline is a weaker base than pyridine? Explain A) hybridization type; B) conjugation type; C) difference
in electronegativity of atoms; D) difference in dimension of atoms.
What RNA base sequence is complementary to the following DNA base sequence G-T-C-A-C-A-T-C-C-G-A? A) G-U-C-A-CA-U-C-C-G-A; B) C-A-G-U-G-U-A-G-G-C-U; C) A-G-U-G-U-A-G-G-C-U-C.