1.

·         I can define the term constitution in organic chemistry.

·         I can explain the octet rule, and I can apply it. I can convert the structural formula
into Lewis’s structure (i.e., add lone electron pairs and formal charges to atoms in a molecule).

·         I can characterize the properties and origin of s- and p-bonds.

·         I can infer the hybridization of an atom from the types of bonds in which the atom
participates (including possible conjugation). I can propose spatial arrangements of small
molecules based on the hybridization of an atom.

·         I can discern systems of conjugated p-bonds, lone electron pairs, and empty p-orbitals.
(i.e., which p-bonds/electron pairs/orbitals are in conjugation).

·         I can write relevant resonance structures, and I can interpret them. I can infer
properties and the electron density distribution in conjugated p-system using the resonance
structures.

·         I can identify the allylic system in the amide, and characterize the consequences of the
conjugation of the lone electron pair on the nitrogen atom and C=O (properties of the peptide
bond).

·         I can determine the polarization of s bond using electronegativity values (typically
bonds carbon-metal, carbon-halogen, carbon-oxygen, and carbon/nitrogen).

·         I can explain the difference between polarization and polarizability of a bond/atom. I
can explain the implication of the polarizability in reactivity (ease of the bond heterolysis).

·         I can define the inductive and mesomeric (resonance) effects. I can determine the effects
and their sign for a given atom or substituent using electronegativity values and resonance
structures (i.e., which substituent is electron-donating and electron-withdrawing).

·         I can distinguish addition, elimination, substitution, and rearrangement reactions. I can
describe and discern the condensation reaction.

·         I can describe and discern electrophiles and nucleophiles.

·         I can use curved arrows to describe the movement of electrons in mechanisms of organic
reactions.

·         I can determine the oxidation number (oxidation state) of an atom in a molecule. I can
identify reduction-oxidation reactions and determine the number of electrons that are exchanged.


                                                2.

·         I can characterize acids and bases according to Brønstedovy-Lowryho and Lewis’s theory. I
can identify pairs of conjugated acids and bases in acid-base reactions.

·         I can apply the significant factors that contribute to the acidity (or basicity) and
assess the acid-base properties of a molecule. The factors are (arranged with concerning their
importance):

1.        Electronegativity and size of the deprotonated atom.

2.       Stabilization of a conjugated base by conjugation.

3.       Stabilization of a conjugated base by the negative inductive effect.

4.       Effect of the hybridization of a deprotonated atom.

5.       Solvation of molecules in aqueous solution.

·         I can compare the relative acidity/basicity of two molecules and determine whose
conjugated base prevails in acid-base equilibrium.

·         I can recall approximate values of pK[a] of selected essential (organic) acids, which are
provided on slide 11 in the presentation.

·         I can use Newman projection, wedge-and-dash image, and Fischer projection to represent
the spatial arrangement of atoms in a molecule. I can mutually interconvert the
projections/formulae.

·         I can define conformation, conformer, and torsional (dihedral) angle. I can describe the
origin of the barrier to conformational movement. I can draw the dependence of the internal energy
of a molecule on the dihedral angle for small alkanes. I can find the conformers on the curve.

·         I can account for the origin of the barrier to conformational movement in amide C-N and
C-C bonds in conjugated p-systems.

·         I can explain the origin of an internal strain in molecules of cycloalkanes (torsional,
angle, and transannular strain).

·         I can name conformers of cyclohexane. I can find axial and equatorial bonds (hydrogen
atoms) in the chair conformer of cyclohexane. I can describe the practical implications of rapid
mutual interconversion of two chair conformers at room temperature. I can describe more stable
conformers of monosubstituted cyclohexanes (equatorial vs. axial orientation of a group).

·         I can define the stereogenic center, isomer, constitutional isomer, stereoisomer,
enantiomer, and diastereomer. I can recognize the type of isomerism in a pair of molecules. I can
define the configuration.

·         I can define the phenomenon of chirality, enantiomer, and racemate. I can describe the
practical consequences of energetic degeneration of the enantiomers. I can characterize methods
used to prepare the enantiomers (separation of enantiomers from racemate, enantioselective
synthesis).

·         I can find a stereogenic center in a molecule (double bond C=C, center of chirality) and
describe its configuration with a proper stereodescriptor (E/Z, cis/trans, R/S). I can distinguish
basic functional groups in organic molecules (their overview is provided in the presentation).

·         I can generate a name of substituted derivatives of hydrocarbons according to IUPAC
rules. The table listing suffixes and prefixes for selected functional groups arranged in the
decreasing order of their priority will be available at the exam test.


                                                3.

·         I can write the mechanisms of monomolecular and bimolecular nucleophilic aliphatic
substitution. I can describe either mechanism with a rate equation. I can explain the change in the
configuration when the substitution reaction takes place on a center of chirality. I can
characterize and find good leaving groups.

·         I can derive structures of products for a given combination of a substrate and a
nucleophile. This includes the nucleophilic substitution of the activated -OH group of alcohols.

·         I can propose an expected nucleophilic substitution mechanism for a given combination of
substrate and nucleophile, considering fundamental factors that facilitate or suppress either
mechanism (steric hindrance, carbocation stability, nucleophile quality, solvation).

·         I can assess qualitatively the basicity and nucleophilicity of basic nucleophiles and
bases (their list is provided in the presentation).

·          I can distinguish mores stable alkene isomers concerning the configuration of the double
bond (cis/trans) and the number of alkyls attached to the atoms of the double bond.

·         I can write the mechanisms of monomolecular and bimolecular elimination of HX. I can
describe either mechanism with a rate equation.

·         I can derive structural formulae of products for a given combination of a substrate and a
base, including regioselectivity consideration based on the product stability (Zaitsev's rule) and
steric hindrance of the base (Hofmann's rule).

·         I can propose an expected mechanism of the elimination reaction for a given combination
of substrate and base, considering fundamental factors that facilitate or suppress either mechanism
(the stability of a carbocation intermediate, quality of a base).

·         I can assess qualitatively the basicity and nucleophilicity of basic nucleophiles and
bases (their list is provided in the presentation).

·         I can describe conditions under which the elimination prevails against the substitution
reaction (structure of the substrate, temperature, property of nucleophile/base).


                                                4.

·         I can describe conditions under which addition to unsaturated hydrocarbons is preferred
and conditions under which this preference can be reversed (temperature, coupling with exergonic
reaction).

·         I can write the mechanism of electrophilic additions of hydrogen halides, water, halogens
(X[2]), and hypohalous acids (HXO) to unsaturated hydrocarbons. I can rationalize Markovnikov's
rule.

·         I can derive structures of main products (including their configuration) from the
structure of reacting molecules for the following reactions: the addition of hydrogen halides (HX),
free radical chain addition of HBr, the acid-catalyzed addition of water, oxymercuration, addition
of water to alkynes, hydroboration-oxidation, hydrogenation (including reduction of a triple
carbon-carbon bond to either cis or trans-alkenes), the addition of halogens (X[2]) and hypohalous
acids (HXO), epoxidation, and syn-dihydroxylation with OsO[4].

·         I can write down products of ozonolysis of alkenes.

·         I can characterize the acidity of terminal alkynes and write the structure formula of its
deprotonation and subsequent alkylation.

·         I can describe the properties of conjugated p-systems.

·         I can write a mechanism of electrophilic addition to conjugated diene, explain the
formation of 1,2- and 1,4-adduct, and characterize conditions under which either product is formed.

·         I can write down the products of the photochemical [2+2] cycloaddition reaction and
Diels-Alder reaction.


                                                5.

·         I can characterize the unique properties of aromatic hydrocarbons. I can apply Hückel's
criteria of aromaticity to identify aromatic and antiaromatic hydrocarbons and heterocycles.

·         I can write and describe the general mechanism of the electrophilic aromatic substitution
reaction (S[E]Ar). I can explain how electrophiles are formed in nitration, Friedel-Crafts
alkylation, acylation, and sulfonation. I can write down the structural formulae of the mentioned
reactions.


·         I can consider the effect of substituents attached to the aromatic ring on SEAr
(activation/deactivation of the ring, preferred position for electrophile attack) using the
inductive and mesomeric (resonance) effects of the substituents.

·         I can write structural formulae of the products of the oxidation of alkylated aromatic
hydrocarbons.

·         I can write and describe the mechanism of the bimolecular nucleophilic aromatic
substitution reaction (S[N]2Ar) proceeding via the addition-elimination mechanism. I can write and
describe the mechanism of the nucleophilic aromatic substitution reaction proceeding via the
elimination-addition mechanism (with benzyne as an intermediate). I can consider factors that favor
either mechanism. I can derive structural formulae of the products of the nucleophilic aromatic
substitution reactions.


                                                6.

·         I can characterize often-used methods to synthesize aldehydes and ketones.

·         I can explain the reactivity of aldehydes and ketones towards nucleophiles. I can
qualitatively assess how the reaction is affected by steric hindrance and the electron-donating or
electron-withdrawing nature of the substituents.

·         I can characterize the reactivity of the enolizable aldehydes and ketones toward
electrophiles. I can determine nucleophilic atoms in enols and enolates.

·         I can write and describe the mechanism of the reaction of aldehydes and ketones with
alcohols under either basic or acidic catalysis (formation of hemiacetals and acetals) and with
water (formation of hydrates – geminal diols).

·         I can characterize the formation of glycosides and the importance of naturally occurring
hemiacetals, acetals, and glycosides.

·         I can write and describe the mechanism of the reaction of aldehydes and ketones with
amines (formation of imines and enamines).

·         I can write structural formulae of the products of reactions in which aldehydes and
ketones react with organometallic compounds, lithium aluminum hydride, sodium borohydride, and HCN.

·         I can write structural formulae of the products of 1,2- and 1,4-addition of nucleophiles
to a,b-unsaturated carbonyl compounds and related systems with electron-deficient C-C double bonds
(Michael addition).

·         I can write structural formulae of the products of Wittig reaction, including the
formation of phosphonium ylides.

·         I can attribute approximate values of pK[a] to various carbonyl compounds. I can assess
the position of enol-keto equilibrium. I can write and describe the mechanism of either acid- or
base-catalyzed enolization of aldehydes and ketones. I can distinguish thermodynamic and kinetic
enolate/enol. I can suggest reagents and conditions for the generation of thermodynamic or kinetic
enolate.

·         I can write structural formulae of the alkylation products of aldehydes and ketones (O-
and C- alkylation), halogenation products, and haloform reaction products.

·         I can write and describe the mechanism and products of aldol reaction and aldol
condensation, including crossed aldol reaction and directed aldol reaction. I can characterize the
importance of aldol-like reactions in biochemistry.

                                                7.

·         I can characterize the properties of carboxylic acids and infer the effect of
substituents on their acidity. I can write down reactants or products of the reactions that are
often used to prepare carboxylic acids.

·         I can identify basic functional derivatives of carboxylic acids (acyl halide, anhydride,
ester, and amide). I can write down and describe the mechanism of nucleophilic acyl substitution
and its products. I can arrange the functional derivatives of carboxylic acids according to their
reactivity toward nucleophiles. I can write down the mechanism and products of a reaction of
functional derivatives of carboxylic acids with organometallic compounds and LiAlH[4]. I can write
down the mechanism and products of acid-catalyzed esterification.

·         I can write down the products of a reaction of carboxylic acid, amide, and nitrile with
LiAlH[4].

·         I can write down the mechanism and products of the Claisen reaction and crossed Claisen
reaction.

·         I can characterize carboxylic acids that are thermally unstable and prone to
decarboxylation (b-oxo acids, acids bearing electron-withdrawing groups on their a-carbon atom). I
can write down structural formulae of the product of the malonic ester syntheses.

·         I can characterize stable functional derivatives of carbonic acid (urea, phosgene,
carbamates) and their properties.


                                                8.

·         I can characterize the structure and properties of alcohol and phenols (their boiling
points affected by hydrogen bonding, their acidity and basicity, and solubility in water). I can
evaluate the effect of the hydrocarbon group on these properties.

·         I can write down structures of reacting compounds, reagents, and products of the
reactions that are often used to prepare alcohols.

·         I can describe the methods that are used to convert the alcoholic -OH group into a good
leaving group (protonation of the -OH group, conversion of an alcohol into an ester of a strong
acid, exchange of the -OH group for halogen).

·         I can write down the structural formulae of products of oxidation of the primary and
secondary alcohols. I can offer reasons for the tendency of the primary alcohols to undergo
overoxidation to carboxylic acids in aqueous media. I can characterize oxidation methods and
reagents that avoid overoxidation and allow the conversion of the primary alcohols into aldehydes.

·         I can describe the redox pair quinone-hydroquinone, including its relevance to
biochemical processes.

·         I can characterize the structure and properties of ethers (their boiling points affected,
their Brønsted and Lewis basicity, solubility in water, and propensity to act as an acceptor of the
hydrogen bond).

·         I can write down structures of reacting compounds, reagents, and products of the
reactions that are often used to prepare ethers.

·         I can describe the reactivity of epoxides. I can write down structures of reacting
compounds, reagents, and products of the reactions that are often used to prepare epoxides.

·         I can write down the structures of products of unsymmetrically substituted epoxide with a
nucleophile without catalysis or under acidic activation of an epoxide.

·         I can characterize the properties of thiols and sulfides (ability to form the hydrogen
bond, the acidity of the -SH bond, and nucleophilicity). I can write down structures of reacting
compounds, reagents, and products of the reactions that are often used to prepare thiols and
sulfides.

·         I can write down structural formulae of products of oxidation of thiols (disulfides) and
sulfides (sulfoxides and sulfones).



                                                9.

·         I can characterize the structure and properties of amines (boiling point, basicity,
acidity) and the effect of hydrocarbon groups on these properties.

·         I can write down products of reactions that are typically used to prepare amines. I can
explain the causes of the low selectivity of the direct alkylation reaction of ammonia/amines. I
can describe the procedure of reductive amination; I can write structural formulae of reductive
amination products. I can suggest starting compounds that can be used to prepare a given amine via
reductive amination.

·         I can write down structural formulae of products of the Hofmann elimination of quaternary
ammonium hydroxides and explain the regioselectivity of this reaction.

·         I can write down structural formulae of products of the reaction of the nitrous acid with
primary and secondary amines. I can describe the properties and usage of the diazonium salts. I can
write down structural formulae of products of the diazo coupling reaction (the electrophilic
aromatic substitution with electron-rich aromatic compounds) and the nucleophilic substitution
reactions that use the diazonium salts.

·         I can characterize the properties of nitro compounds, their preparation methods, and
their reduction products.

·         I can characterize the structure of the organometallic compounds. I can describe the
reactivity of the compounds with a carbon-metal bond (basicity, nucleophilicity, and ability to
reduce carbonyl compounds).

·         I can write down structural formulae of the starting compounds and products of the
reactions that are used to prepare organometallic substances (the reaction of organohalogen
compounds with metals, deprotonation of the acidic C-H bonds, and transmetallation). I can
rationalize the incompatibility of carbon-metal bonds with some functional groups.

·         I can write down structural formulae of the starting compounds and products of the
reactions of organometallic compounds with acids, aldehydes, ketones, epoxides, nitriles, carbon
dioxide, and functional derivatives of carboxylic acids.

·         I can characterize the reactivity of organometallic compounds containing a transition
metal.

·         I can write down structural formulae of the products of the Gilman reagents (R[2]CuLi)
reactions with acyl halides and a,b-unsaturated aldehydes and ketones.


                                                10.

·         I can characterize effects that stabilize alkyl radicals. I can arrange the alkyl
radicals according to their stability (or homolytic bond dissociation energy of C-H bonds).

·         I can describe the mechanism and rationalize the selectivity of the radical halogenation
of hydrocarbons. I can characterize how the selectivity of the reaction is affected by the
dissociation energy of various C-H bonds and the number of chemically equivalent hydrogen atoms for
chlorination and bromination. I can explain the selectivity of halogenation reaction in terms of
halogen’s reactivity.

·         I can characterize methods and reagents used in the halogenation of unsaturated
hydrocarbons in which the addition of halogen competes with radical substitution.

·         I can describe reactants, products, and mechanism of the autooxidation of organic
compounds. I can characterize the occurrence and use of these compounds.





                                                11.

·         I can characterize the chemical structure and properties of monosaccharides,
oligosaccharides, and polysaccharides.

·         I can define and explain the following terms: d- and l-sugar, epimer, anomer, reducing
and nonreducing sugars, and mutarotation.

·         I can transform the Fischer projection of monosaccharide into the Haworth projection of
its furanose or pyranose form (including both anomers).

·         I can characterize the structure and occurrence of the derivatives of saccharides
(acetals, O- and N-glycosides, esters, amines, sugar alcohols, and carboxylic acids derived from
carbohydrates).

·         I can explain the mechanism of the monosaccharide epimerization/isomerization and
retro-aldol reaction in the basic solution.

·         I can describe the structure, properties, function, and occurrence of selected mono-,
oligo- and polysaccharides (information provided in the lecture slides).

·         I can describe the structure of heterocyclic compounds. I can recognize and assign
trivial names to essential heterocyclic compounds (a list of the compounds is provided in the
lecture slides).

·         I can characterize the properties and reactivity of five-membered aromatic heterocycles.
I suggest suitable reagents for electrophilic aromatic substitution with these heterocycles. I can
write down structural formulae of the products of these reactions.

·         I can describe the properties of pyridine and its derivatives toward electrophiles and
nucleophiles. I can write down structural formulae of the products of these reactions.

·         I can characterize the occurrence, function, and significance of porphine, pyrimidine,
and purine derivatives.

·         I can characterize the structure and (acid-base) properties of amino acids. I can
describe the properties of the peptide (amide) bond.

I can describe methods used to synthesize peptides in the laboratory – protection and deprotection
of the amino and carboxylic groups and activation of the carboxylic group to accomplish the
coupling of amine and the acid. I can describe the solid-phase synthesis of peptides.

                                                12.
  * I can characterize the lipids and their properties.
  * I can describe the chemical structure of the lipid categories (waxes, triacyl glycerides,
phospholipids, sphingolipids, terpenes, steroids, and prostaglandins). I can assign the structure
of the lipid to the appropriate category.
  * I can characterize the structure of the fatty acids. I can describe the effect of the carbon
atom number and the presence of the double bond of the properties of the fatty acid and their
derivatives.
  * I can describe the function and biological effects of the lipid categories.
  * I can characterize chemical transformations of the lipids and the fatty acids (hydrolysis,
autooxidation, transesterification, hydrogenation) and write down structural formulae of these
reactions.
  * I can explain the surface activity of soap, the formation of micelles and the lipid bilayers.