Instructions: Try answering the questions. No need to

submit. If we have time, we will discuss the questions.

I. Calculate the index of hydrogen deficiency of the

following compounds. Propose all possible structures

(Only structures that obey the octet rule are valid)

1. C4H6

2. C4H9N

3. C6H6Cl6

4. C7H8O2N

5. C4H6O

II. Draw the structures of the compounds based on their

IUPAC names/common names:

1. 1,1,1-trichloro-2,2-di(4-chlorophenyl)ethane

2. 9, 10-dibromophenanthrene

3. 2-methylpropylbenzene

4. 6-ethyl-3,4-dimethyloctane

5. 4-ethyl-2-methyl-1-propylcyclohexane

6. 1-ethyl-2-iodocycloheptane

7. 4-bromo-2-chloro-1methylcyclooctane

8. 4-methyl-1,3-pentadiene

9. 4-bromo-2-methyl-2-pentene

10. 1-bromo-5-methyl-3-hexyne

11. 6-bromo-3-chloro-4-methylcyclohexene

12. bicyclo[3.2.0]heptane

13. 4-ethyl-3-methylcyclohexene

14. (E)-3-hexene

15. di-tert-butylacetylene

16. 5,6-dimethyl-2-heptyne

17. (E)-2-phenyl-2-pentene

18. 2-chloroanthracene

19. m-chlorosytrene

20. o-nitroanisole

21. (Z)-1,3,5-tribromo-2-pentene

22. (E)-1,2-dibromo-3-isopropyl-2-hexene

23. 2,3,3,4-tetramethylheptane

24. 2-methyl-4-(1-methylethyl)octane

25. 6-ethyl-2,3-dimethylnonane

III. Which of the following names are correct? Correct

the incorrect ones.

1. 4-heptyne

2. 2-ethyl-3-hexyne

3. 4-chloro-2-pentyne

4. 2,3-dimethyl-5-octyne

5. 4,4-dimethyl-2-pentyne

6. 2,5-dimethyl-3-hexyne

7. 5-methyl-6-heptyne

8. 3-propyne

IV. Name the following compounds based on their

structures:

1.

2.

3.

4.

5.

6.

7.

8.

9.

10.

11.

12.

13.

14. CH2=C(C2H5)CH2CH2CH3

15. (CH3)2C=CHC(C2H5)=CH2

16. (Assign E/Z)

17. (Assign E/Z)

V. A mixture of isomers was found to contain 8 carbons.

The rest are hydrogens. The degree of unsaturation was

found to be 4 for all isomers. What is the formula? The

aromaticity of each individual compound was not

destroyed upon subjecting to high pressure and

temperature. What conclusions can you draw with

respect to the functional groups present in the mixture?

Draw structures to support your answer/s.

VI. How many primary, secondary and tertiary carbons

does the compound have? What is the common name of

this compound?

Alcohols, Ethers, Amines, and Carbonyl Compounds

I. Write ALL structures based on the molecular formula

of the specified compounds. You are allowed only a

maximum of three structures if there are multiple

structures.

1. C8H8O2 (carboxylic acid)

2. C5H13N (tertiary amine)

3. C4H10O (secondary alcohol)

4. C6H12O (aldehyde)

5. C8H18O (symmetric ether)

6. C6H12O (ketone)

7. C8H16O4 (cyclic ether)

8. C6H10O3 (unsymetric anhydride)

9. C10H12O2 (ester)

10. C8H7ON (primary amide)

II. Draw the structures of the following compounds.

1. N,N-dimethylhexanamide

2. Propanenitrile

3. Propionyl bromide

4. Benzoic anhydride

5. β-valerolactone

6. Cycloheptanecarboxylic acid

7. Isopropyl propanoate

8. 4-chlorobutanamide

9. 3-methyl-2-oxacyclohexanone

10. N-ethyl-N-methylpentamide

11. 4-hexenal

12. Diisopentyl ketone

13. 4-methyl-5-oxohexanal

14. Benzene-1,3-dicarbaldehyde

15. γ-bromovaleraldehyde

III. What is the systematic name of the following acids?

(1) (2) (3)

(4) (5)

IV. Patty found that her compound has a molecular

formula C9H8O3. She then hydrolyzed this compound.

After 5 minutes of heating, Arwin, her lab mate noticed a

familiar smell of vinegar. Afterwards, Patty then added

an excess amount of NaOH to the mixture. Upon cooling

to 4oC, solid white crystals can be seen floating on the

surface of the mixture. What is the structure and name of

Patty’s unknown.

“Study hard and you will be rewarded. Fail to do so and the

consequences may be severe.”

- Harry Potter and the Order of the Phoenix