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Friday, November 30, 2007

Stereochemistry. Stereochemistry absolute and relative. The D-glyceraldehyde. L-glyceraldehyde. Fischer projections. Steric series. Molecules with two chiral centers. Assignment of absolute configurations in Fischer projections. Attribution of the absolute stereochemistry according to the rules of priority. Relation between relative and absolute stereochemistry. RX. The three tartaric acid. Forms meso. Molecules with multiple chiral centers. Fragrance of alcoholic solutions at 10% of R-limonene and D-limonene. Molecules with several chiral centers. Differences between enantiomers and diastereoisomers. Biological implications. D-glucose and L-Glucose.

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lectures and exercises of November 28, 2007

organic and inorganic acids. Nitric acid and nitrous acid. Structures of the resonances of nitrite and nitrate ions. Differences in acidity. Ka and pKa. Carboxylic acids. Difference in acidity between a carboxylic acid and alcohol. Butyric acid and 1-butanol. Substituted carboxylic acids. Chloroacetic acid, dichloroacetic and trichloroacetic. Acidity in Chemistry Organic. Comparison of the acidity of alcalni, alkenes and alkynes and related to the hybridization of carbon atoms.
hydroxy acids. Succinic acid, malic and tartaric. Lactic acids.

diatereoisomeri enantiomers. Definition chiral carbon. Interaction of chiral molecules with polarized light. Molecules with a chiral carbon. Lactic acid R-and S-lactic acid

Three-dimensional models. Molecules with two chiral carbons. 2n rule. The four stereoisomer of 2,3-dihydroxybutyrate. Assignment of absolute configuration according to the rules of priority.

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Wednesday, November 21, 2007

lectures and exercises

Functional Groups. Installing and using software in organic chemistry. Main functions. Molecules in 3D. Alcohols to 4 carbon atoms in molecular formula C 4 H ₁₀ O. Structural isomers. Relationship between structure and properties. A fragrance alcohol of formula C H 4 10 O. 10% ethanol solution of 1-butanol, 2-butanol, 2-methyl-1-propanol, 2-methyl-2-propanol.

aldehydes and ketones. Nomenclature.

derivatives of carboxylic acids: esters. Acid component and alcohol component. Nomenclature. Butyl acetate. Butyl butyrate.

nitrogen-containing organic compounds: amines. Sp3 hybridization of the nitrogen atom. Primary amines, secondary and tertiary. Nomenclature. Basic properties of the amines. Definition of Acids and Bases second Brønsted and Lewis.

Derivatives carboxylic acid: amides. Difference between amines and amides. Resonance. Organic molecules containing the amino group as substituent. Amino acids. Peptides. The amide bond. No rotation around the amide bond.

Alkyl halides.

Introduction to stereoisomerism. Alkenes. 1-butene, 2-butene. Geometrical isomers. The symbols E and Z. Rules of Priority. Applications.

polyenes. Beta-carotene

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Thursday, November 15, 2007

Functional Groups. Molecules containing organic C, H, O. Alcohols and ethers. Structural isomers. Primary alcohols, secondary and tertiary. Relationship between structure formula and physical properties. Intermolecular bonds. The case of C2H6O. Boiling point and solubility. Polyols. Ethylene glycol and glycerin. Carbonyl compounds. Aldehydes and ketones. Nomenclature. Organic molecules containing several functional groups. Priority groups. Carboxylic acids

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Wednesday 14 November 2007.

Introduction to Organic Chemistry. Organic and inorganic molecules. The formation of the elements. Carbon. Atoms and isotopes. The formation of chemical bonds. Electronic configuration of carbon. Hybridization sp3, sp2 and sp. Hybridization and molecular geometry. Sp3 hybridization and alkanes. Introduction to structural isomers. Nomenclature. Sp2 hybridization and alkenes. sp hybridization and alkynes.

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first test exemption

November 27, 2006

1. Write the Lewis structures of the molecules listed below and determine the hybridization of the carbon present. a) carbon dioxide; b) potassium carbonate c) Bromotriclorometano d) Hydrogen cyanide, e) Formaldehyde f) formic acid. (4)

2. Giving names to the molecules described below: (6)




3. The IUPAC name acid threonine protein is present in the acid 2-amino-3-hydroxybutanoic. Write all possible stereoisomers and indicate those belonging to the series steric L. (5)

4. dicarboxylic acids succinic, malic and tartaric acid are all present in varying amounts in wines. They are 0, 1 and 2 hydroxyl in the structure that contains a total of 4 carbon atoms. Write the structure and give the IUPAC name to all acids. Also indicate the presence of chiral centers and write the corresponding stereoisomers. (8)

5. Indicate the relationship between acid isomers (2S, 3R)-3-fluoro-2-hydroxy butanoic 1 and the structures af. (7)

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written exam of 20 Nov. '06

a . Write the structures of these molecules to
) 2-chloro-3 ,4-diidrossipentanale b) acid 3-amino-2-fluoro-4-nitrobenzoate; c) 2,2,3,3-tetrametilciclobutanone d) ( 2E) -4.5-dimethyl-2-hexene; e) acid (2S, 3R)-2-amino-3-methylpentane; f) How many stereoisomers of the molecule and there)?

2. Identify the functional groups present in vitamin C, whose structure is as follows

3. Write entries for the second acidity increasing the molecules listed below: a) 2-nitrophenol b) phenol, c) 2-methyl-ciclopropanolo d) acid 3-fluorobutanoico e) cloropropanoico acid 2-f) methyl-cyclobutane;

4 . Give an explanation of the fact that cyclohexene reacts rapidly with bromine, while benzene is inert.

5. Write the structure of a) a D-amino acid, b) an L-chetoesoso c) a triglyceride; d) a nucleoside; e) an ester.

Script ORGANIC CHEMISTRY
Degree Viticulture and Enology January 19, 2006

a . Naming the structures shown.

2. Sort monosaccharides whose structures are given below.

3. Identify and give a few examples of what are the conditions under which a chemical species to be defined as aromatic.

4. How could a separate, 3.5-cyclohexane Tribromo from cyclohexylamine?

5. Write the structures of the following substances: a) a D-amino acid, b) An L-aldopentoso c) The triglyceride formed by acid butyric acid. (6)


degree in Agricultural Science and Technology
Written Examination Organic Chemistry (21 July '05)

1. Write the structures of these molecules
a) 2,3-dihydroxy-4-metilesanale b) (2S) 2-Amino-3-methylpentane; c) dimetilciclobutanolo 1,2-d) (2E, 4Z) -2,4-hexadiene; e) acid, 2,4-dimethyl-3-nitrobenzoate.

2. Draw all possible stereoisomer of 2,3-dihydroxy-butandioco.

3. Write entries for the second increasing acidity of the molecules listed below: a) 2-nitrophenol b) 4-methylphenol; c) 2-methyl-cyclohexanol; d) acid 2-fluoropropanoico e) iodoesanoico acid 3-f) 1, 1.2-trimetilciclopropano.

4. Explain why the hydrocarbon 1,3-cyclopentadiene acts as an acid (pKa ≈ 15) while the cyclopentene no (pKa ≈ 40).

5. Write the structure of a) an L-amino acid, b) a D-chetopentoso c) a monoglyceride d) a nucleotide e) an acetal.


second test exemption ORGANIC CHEMISTRY
Degree Viticulture December 18, 2006 and Enology

6. Naming the structures shown, explaining the observed acidity scale.

7. Sort monosaccharides whose structures are given below.

8. Indicate which between chemical species proposed below can be defined as aromatic.

9. Describe a method to separate the 3.5-by 1.3-dietilanilina dietilbenzene.

10. Write the structures of the following substances: a) a dipeptide composed only by D-amino acids b) The anomeric a D-closed form aldotreoso furanosica c) The diglyceride formed by acid butyric acid.

Degree Viticulture and Enology
WRITTEN EXAMINATION ORGANIC CHEMISTRY February 19, 2007

11. Naming molecules below, specifying for each possible number of stereoisomers.

12. Please indicate which features should have an aromatic organic molecule to be defined.

13. Illustrate a method for separating acid from 3-METHYLBENZOQUATE chlorobenzene.

14. Write the generic structures of the following substances: a) a D-aldochetoso b) a b-amino acid, c) the triglyceride formed by acid butyric d) a cyclic hemiacetal, e) a nucleoside present in DNA; f) monounsaturated fatty acid.

15. Write entries for the second growing basicity structures of the molecules shown below. a) Ethylamine b) diisopropylamine; c) Ammonia; d) Aniline e) 4-nitroaniline; f) 1,3,5-trimethylbenzene.

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Written exam Written exam Written exam

21 September '05

1. Write the structures of these molecules
a) 3,4-dicloroeptanale b) acid 3-amino-2-chloro-4-etilbenzoico c) 1,2,2-trimetilcicloutanolo d) (2Z)-4-methyl -2 pentene e) 5-metilciclopent en-2-amino-1-f) How many stereoisomers of the molecule and there)?

2. Identify all the functional groups present in vitamin A (retinol), whose structure is as follows.

3. Write entries for the second increasing acidity of the molecules listed below: a) 4-nitrophenol b) 4-methylphenol; c) 2-methyl-cyclohexanol; d) acid 3-fluoropropanoico e) cloroesanoico acid 2-f) 1, 1.2-trimetilciclobutano;

4. Explain the difference in acidity observed in the propane CH3-CH2-CH3 (pKa = 50) propylene, CH3-CH = CH2 (pKa = 40) and propina CH3-C ≡ CH (pKa = 30).

5. Write the structure of a) an L-amino acid, b) a D-chetoesoso c) a diglyceride d) a nucleoside; e) an ester.

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July 21 '05

1. Write the structures of the following molecules:
a) 2,3-dihydroxy-4-metilesanale b) (2S) 2-Amino-3-methylpentane; c) dimetilciclobutanolo 1,2-d) (2E, 4Z) -2,4 hexadiene-e) acid, 2,4-dimethyl-3-nitrobenzoate.

2. Draw all possible stereoisomer of 2,3-dihydroxy butandioco.

3. Write entries for the second increasing acidity of the molecules listed below: a) 2-nitrophenol b) 4-methylphenol; c) 2-methyl-cyclohexanol; d) acid 2-fluoropropanoico e) iodoesanoico acid 3-f) 1, 1.2-trimetilciclopropano.

4. Explain why the hydrocarbon 1,3-cyclopentadiene acts as an acid (pKa ≈ 15) while the cyclopentene no (pKa ≈ 40).

5. Write the structure of a) an L-amino acid, b) a D-chetopentoso c) a monoglyceride d) a nucleotide e) an acetal.

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Programme of Organic Chemistry

Degree in Viticulture and Enology
4 CFU

Professor: Lombard (luilongo@unina.it)
students must use the address: luilongo@gmail.com

Recommended text:

John McMurry, "Fundamentals of Organic Chemistry " Zanichelli Editore, 2005

Software: ACD / ChemSketch freeware ( http://www.acdlabs.com/ )

Other recommended reading :

Penny Le Couteur, Jay Burreson " The buttons of Napoleon. How 17 molecules changed history " Longanesi publisher (series lens of Galileo) , 2007.

Objectives: The course
aims to provide the knowledge base of the structural theory of organic molecules in order to understand and interpret the molecular diversity of natural products and those arising from the processing of chemical and enzymatic.

Prerequisites: General Chemistry


Program:
Introduction to organic chemistry. Atoms, the carbon molecules. Orbitals, bonds, hybridization. Lewis formulas. Resonance. Saturated and unsaturated hydrocarbons. Classes of organic compounds. Nomenclature. Using Software in organic chemistry. Structural isomers. Cis-trans geometry. Absolute and relative stereochemistry. Chirality. Enantiomers and diastereoisomers. Aromaticity aromatics. Acidity and basicity in organic chemistry. Amino acids, peptides and proteins. Carbohydrates. Acetals. Monosaccharides and polysaccharides. Nucleic Acids. Lipids.