ASSIGNMENT 1 BKF1323

Topic: Introduction, Stereoisomers and Chirality

A. Classify and name all the compounds based on their given formulae:

1. CH2(OH)2 2. C3H6 (cyclic, saturate) 3. (CH3)3N 4. CH3COOH

5. CH3CHOHCH3 6. C5H9OH (cyclic) 7. C6H6 (cyclic, unsaturate) 8. CH2(COOH)2

9. (C3H7)2O 10. (C3H7)2CO 11. C3H7COOC3H7 12. CH2O

13. C10H20 (unsaturate) 14. C3H5(OH)3 15. CH2F2 16. C2H3Cl (unsaturate)

17. C2H2 18. C4H4Br4 (cyclic, saturate) 19. CH3COOK 20. C6H5NH2 (aromatic)

B. Categorize these compounds:

1. Methylene glycol
2. 3-hexene
3. Fluoromethanol

C. Draw a structural formula using an example for each term as follows: chiral, achiral, enantiomers
and diastereomers.

Topic: Alkanes @ Paraffins

A. List the alkanes contained in crude black gold:

1. LPG 2. Gasoline 3. Kerosene 4. Diesel 5. Cokes

B. Explain through mechanism diagram how:

1. Formylene chloride is formed from mixture of liquefied methane and chlorine?

2. Methylene fluoride is formed from mixture of liquefied methane and fluorine?
3. 2-butylene is synthesized from butane?

C. Describe using an example for each alkane synthesis through these ways:

1. Alkylation of terminal alkynes.

2. Reduction of alkyl halides.
3. Corey-House-Posner-Whitesides synthesis from alkyl halides

Topic: Alkenes @ Olefins

A. Draw the skeletal formulae of the following olefins and assign either it is E or Z isomer:

1. 1-fluoro-3-bromo-2-pentene
2. 4,4,4-trichloro-2-methyl-2-buten-1-ol
3. 3-bromo-3-hexen-1,4-diol
4. 3-amino-2-butene
5. 3-amino-5,5-dichloro-4-difluoromethyl-3-octene

B. Explain through mechanism diagram:

1. The preferred product formed if propylene is mixed with steam.

2. The confirmed product formed if 2,3-pentadiene is mixed with excessive hydroiodic acid.
 3. The stable product formed from dehydrogenation at 2 nd and 3rd C atom in butane.

C. Describe:

1. Propylene synthesis through tosylation of propyl tosylate (p-propyl toluene sulphonate).

2. An example for ozonolysis of alkenes to produce carbonyls.
3. An example for oxidative cleave of alkenes to produce carbonyls.

Topic: Alkynes

Explain through mechanism diagram:

1. How 2-pentyne becomes diethyl ketone when hydrated, not pentene glycol?
2. How 2-butyne does not directly become 2,2,3,3-tetrafluorobutane when excessively
fluorinated?
3. The confirmed product formed if propyne is mixed first with limited pure hydrofluoric acid
followed with limited steam.

Topic: Mix of all above

You are supposed to produce several products using linear saturated compound (total carbon atoms
= 8) as starting material.

a. Draw its skeletal formula.

b. Name these following compounds based on 8 total carbon atoms for each compound:
i. 6 carbon atoms form a ring, the rest attach at 1st and 4th carbon atoms in the ring
ii. 6 carbon atoms form a line, the rest attach at 2nd and 5th carbon atoms in the line
iii. 5 carbon atoms form a line, the rest attach at 2nd and 4th carbon atoms in the line
iv. 4 carbon atoms form a ring, the rest attach at all carbon atoms in the ring
c. What are the products when the starting material is once dehydrogenated at 4th carbon
atom?
d. List all three (3) products obtained if the products from part c is mixed with aqueous
chlorine.
e. What is the product when the starting material is twice dehydrogenated at:
i. 3rd carbon atom?
ii. 4th carbon atom?
f. Draw the structural formulae of all four (4) products obtained when the product from part e
is once hydrohalogenated with hydrofluoric acid. Predict E and Z isomers for each product.
g. State the main application of
i. Major product obtained from part d.
ii. Products obtained from parts c and e.