Introduction to biochemistry for dentistry students

Workbook

4th week

Repeating of organic chemistry;

To practice organic chemistry for biochemistry

Written by: Attila Agócs, Zoltán Berente, Gergely Gulyás, Péter Jakus, Tamás Lóránd,

Veronika Nagy, Erika Radó-Turcsi, Anikó Takátsy

Edited by: Peter Jakus

Name: Group: Date:

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Pre-lab test questions

1. Calculation of pH for a strong acid/base solution from the amount or concentration of the solute (calculator is required).

2. Calculation of pH for a weak acid/base solution from the amount or concentration of the solute (calculator is required).

3. Write the name or structural formula of a given inorganic or organic compound.

4. Give the reaction equation for the water addition of ethene.

5. Give with structural formulas the water elimination reaction of isopropanol. Which type of compound forms?

6. How does the negative inductive effect influence the acid strength of the carboxylic acids? Give an example.

7. Write the reaction equation for the oxidation of a primary alcohol with structural formulas. Which family of compounds

does the product belong to?

8. Write the reaction equation for the oxidation of a secondary alcohol with structural formulas. Which family of compounds

does the product belong to?

9. Write reaction equation for the reduction of an aldehyde with structural formulas. Which family of compounds does the

product belong to?

10. Write the reaction equation for the oxidation of an aldehyde with structural formulas. Which family of compounds does

the product belong to?

11. Write reaction equation for the reduction of a ketone with structural formulas. Which family of compounds does the

product belong to?

12. Give the general reaction equation of acetal formation with structural formulas. (It shuld complete with semiacetal next year)

13. Write reaction equation for the mild oxidation of ethane thiol (ethyl mercaptan) with structural formulas! Which family of

compounds does the product belong to?

14. Give the reaction equation for the formation of a Schiff base (imine) with structural formulas.

15. Write the reaction equation for the formation of a carboxylic acid ester with structural formulas.

16. What does the order (type) of alcohols mean? Give the type of the following alcohols: 2-methyl-2-propanol, isopropanol,

benzylalcohol. Give their formulas, as well.

17. Write the reaction equation for the decarboxylation of a monocarboxylic acid with structural formulas.

18. Give the reaction equation for the aldol addition (aldol dimerisation) with structural formulas.

19. Give the equation with structural formulas for the oxo-enol tautomerisation of acetone. Indicate the more stable form.

20. Explain the difference between the lactam and lactim functional groups giving the structure of two compounds.

21. What does the ’quinoidal electron system’ mean? Give a specific example with structural formula.

22. Draw the conversion of dihydroxyacetone to glyceraldehyde. What kind of reaction occur?

23. Give the reaction equation with structural formulas for the base catalyzed hydrolysis of ethylbutyrate.

24. Draw the formation of gamma-butyrolactam from gamma-amino-butyric acid.

25. Draw the formation of gamma-butyrolactone from gamma-hydroxo-butyric acid.

26. Write a structural equation for peptide-bond formation from two amino acids.

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1. POLYMERIZATION, ADDITION, CONDENSATION, ELIMINATION, SUBSTITUTION

What do we call polymer? What is a monomer? How do we denote the polymer in the structural formula? Types of polymer formation: 1. addition and 2. condensation 1. a) What is the definition of addition? b.) Write the addition of at least 3 ethene molecules with a structural formula. Does the reaction proceed without a catalyst?

2. a) What is the difference between addition and condensation?

b.) Write the condensation formation of nylon from adipic acid and 1,6-diaminohexane!

3. What does the elimination mean? Write an example with a structural formula!

4. What does the substitution mean? Write an example with a structural formula!

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2. HETEROCYCLIC COMPOUNDS. Fill in the tables according to the specified conditions!

a.) Give the names of the compounds. b.) Specify the acid-base character of the compounds. c.) In which compounds does the aromatic electron configuration develop? Explain your answer! d.) Give an example of the biological occurrence of the compound if you know it!

A

C

E

G

I

K

B

D

F

H

J

L

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3. COMPOUNDS TO BE RECOGNIZED

a.) The figure I.) is the morphine, the II.) one is called heroine.

b.) Establish which one has a higher logP value. State your reason.

c.) Name the heterocyclic ring in the compound! d.) Name i) the type of the numbered hydroxyl groups, ii) their acid-base character and iii) their relative spacing in morphine (identical, similar, different, opposite)! 1 i) ii) 2. i) ii) iii)

e.) How can be synthesized the II.) compound from the I.) one? (What is the structural difference?)

f.) What is the physiological effect of the compounds? g.) Mark with asterisk the chiral carbon atoms in morphine. h.) Give the name of the following compound. Which family of compounds does belong to?

I…………………………………………… II…………………………………………… III………………………………

i.) Give the polar-apolar nature of compound I). What is the role of it in digestion?

j.) Give the polar-apolar and acid-base character of compound II).

k.) Mark the ester and glycoside bond with compound III. In which nucleic acid is the compound recognized? Is the compound

a reducing agent?

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l.) Mark with asterisk the chiral carbon atoms in compound I.

4. AMINOACIDS, PROTEINS

a.) What type of reaction is the formation of polypeptides? b.) Which amino acid has secunder nitrogen atom? c.) Which amino acid does contain thiol group? d.) Which amino acid is achiral? e.) Which amino acid can isomerizes to cis-trans form? f.) Which amino acid does contain sulphide group? g.) Which amino acid is capable of forming a disulfide bond? What is its biological significance?

h.) Which amino acid does contain primary alcoholic hydroxyl group? i.) Which amino acid does contain secondary alcoholic hydroxyl group? j.) Which amino acid does contain phenolic hydroxyl group? k.) What is the importance of alcoholic, phenolic hydroxyl group in enzyme regulation? k.) Which amino acid does contain imidazole ring? What is the biological importance? l.) Which amino acid does contain indole ring? What do you state about the light absorbance of it? 5

m.)* Which amino acid hydroxylations are essential for synthesis of collagen? What is the cofactor of the hydroxylation? What is the name and main symptom of the disease that develops in the absence of cofactor?

n.) Define the isoelectric point of amino acids, proteins. o.) Name the following peptide! Which is the first amino acid?

I. II.

………………………………………………………………………………………

………………………………………………………………………………………

p.) Explain the buffer effect of the amino acids. Write the equation for the operation of physiological buffers!

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50%-50% 50%-50%

buffereffect

(pK1+pK2)/2

5. CARBOHYDRATES

5.1.) What is the definition of carbohydrates? What do carbohydrates end with?

a.) Give examples for mono-, di- and polysaccharides.

b.) How do you classify the carbohydrates by numbers of carbon atom? Name them!

4C→ 5C→

6C→ 7C→

c.) How do you classify the carbohydrates by function groups?

A) B)

5.2.) Which is the simplest carbohydrate?

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5.3.) What is the rule for numbering carbohydrate carbon atoms?

5.4.) What is the stereochemical relationship between D-erythros and D-threos? See the illustration below.

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5.5.)

5.6.) a.) How can you define the concept of diastereomers most briefly?

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b) Name the C-2 epimer of D-galactose!

c) Is D-galactose epimer’s for

D-mannose?

5.7.) Do you know the α and β anomeric terms? What does it mean? Are carbohydrates in solution more open or ring-shaped? What makes glycoside -OH?

5.8.) What is the difference between pyranose and furanose form? * Can a fructose be in the piranose form?

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5.9.) What is the most characteristic chemical property of the aldehyde group? (eg why is acetaldehyde toxic?) Is glucose toxic? If yes, why, if not, why? Justify your answer!

Does fructose give the silver mirror test? Do ketoses generally give a silver mirror test? Explain your answer! 5.10.) In which chemical properties does the glycoside -OH differ from the alcoholic -OH group?

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5.11.) Which of the following carbohydrates are reducing properties?

F G