General Organic & Biological Chemistry Review I1I

CHE 2100 Fall 2013

General Organic & Biological Chemistry Review I1I

A general note: Short answer questions are just that, short. Writing a paragraph filled with every term you can remember from class won’t improve your answer— just answer clearly, succinctly, and in your own words.

1. Circle the molecule that would be expected to have the lowest boiling point. Explain why.

3-pentanone ethoxy propane pentanal pentanol

2. Which of the following compounds will undergo oxidation using potassium dichromate to form a carboxylic acid?

3. Explain why a ketone cannot be easily oxidized into a carboxylic acid.

4. Can 2,4-dimethyl-3-pentanone undergo keto-enol tautomerization?

5. Write the product or products of the below reaction. What is the name of this reaction type?

6. Draw the line-angle formula of 2-methylpropyl butanoate.

7. Name the following molecules:

8. Draw the line-angle formula of hexadecanoic acid.

9. Which would you expect to have a higher melting temperature, decanoic acid or

dec-6-enoic acid?

10. Why are our bodily stores of energy called “fatty acids”?

11. Draw the mechanism of the hydrolysis of 2-methylpropyl ethanoate.

12. Draw the before and after states of the formation of a cyclic hemiacetal from erythrose ( 2,3,4-trihydroxy butanal )

13. Draw the following molecules:

cis-1,2-diethyl-cyclopentene 5-bromo-3-isoproyl trans-hex-2-ene thiol

2-methylpropyl 2-chloropropyl ether 4-amino-5-hydroxyoctanoic acid

14. Industrially, we often need ethanoic acid. The starting material for this product is usually ethane. Show below a series of reactions that would transform ethane to ethanoic acid.

15. What is saponification?

16. What type of biological molecules includes many hemiacetals?

17. Name the following molecules:

18. Name a reaction that could be used to (I) create AND a reaction that could be used to (II) destroy/react away the following types of molecule:

Alcohol Aldehyde

Carboxylic acid Alkene

19. Rank the following molecules from lowest boiling point (4) to highest boiling point (1):

___ CH3COOCH2CH3 , ___ CH3CH2OCH2CH3 ,

___ CH3CHOHCH3 , ___ CH3COCH2CH3

20. Name the molecules in question 18.

21. Draw an example of keto-enol tautomerization. Names both forms.

22. Draw the following structures:

3-ethyl-5-cyclopropyl-2-pentanol cis-6-methyl-3-heptenal

2,5,6-trimethyl-2,5-heptadiene-4-one cis,cis-6-bromo-2,4-hexadienoic acid

23. Draw the reaction of propanal with 2-propanol to create a hemi-acetal.

24. Name two ester-containing biological molecules.

25. Why are carboxylic acids more acidic than alcohols?

26. Why is it impractical to make amides by reacting a carboxylic acid with an amine?

* 27. Draw the enantiomer of the following molecule:

* 28. What requirements must a carbon atom have to be chiral?

* 29. How many stereocenters are present in the following compound?

* 30. How many stereoisomers are possible for the following triglyceride (Include all types of stereoisomerism)?

* 31. Which of the following pairs of stereoisomers are related as enantiomers?

* 32. Progesterone, which is present in humans as a single stereoisomer, has six stereocenters. Human progesterone is one of how many possible stereoisomers for this structure?

* 33. Dextrorotatary compounds rotate plane-polarized light in which direction?

* 34. The drugs Prilosec and Nexium both contain the same active ingredient. Nexium contains a single enantiomer but Prilosec is a racemic mixture. Which drug will be more effective if you receive a 20 mg dose of each? How much more effective?

35. Describe the sequence of reactions needed to go from a starting material of propane to isopropoxy 2-propanol.