Download Review 3 - Bonham Chemistry

CHE 2100 Fall 2012
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. Draw and give the IUPAC name for the simplest possible Aldehyde and simplest possible
Ketone.
2. Circle the molecule that would be expected to have the lowest boiling point. Explain why.
3-pentanone
ethoxy propane
pentanal
pentanol
3. Which of the following compounds will undergo oxidation using potassium dichromate to
form a carboxylic acid?
4. What is the primary purpose of oxidation in biology?
5. Draw and name the oxidation product for the following reaction:
6. Name two biologically-occuring molecules that contain aldehydes.
7. Explain why a ketone cannot be easily oxidized into a carboxylic acid.
8. How many ketone functional groups are presenting the following molecule?
9. Can 2,4-dimethyl-3-pentanone undergo keto-enol tautomerization?
10. Draw and name the product of the following reaction:
11. Write the product or products of the below reaction. What is the name of this reaction
type?
12. Draw the line-angle formula of 2-methylpropyl butanoate.
13. Name the following molecules:
14. Draw the line-angle formula of hexadecanoic acid.
15. Which would you expect to have a higher melting temperature, decanoic acid or
dec-6-enoic acid?
16. Why are our bodily stores of energy called “fatty acids”?
17. Draw the mechanism of the hydrolysis of 2-methylpropyl ethanoate.
18. Draw the before and after states of the formation of a cyclic hemiacetal from erythrose (
2,3,4-trihydroxy butanal )
19. Are phenols more or less acidic than other alcohols? Why?
20. 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
21. 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.
22. What functional group does not react with acid or base, nor most oxidizing or reducing
agents?
23. What is saponification?
24. What type of biological molecules includes many hemiacetals?
25. Name the following molecules:
26. 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
27. Rank the following molecules from lowest boiling point (4) to highest boiling point (1):
___ CH3COOCH2CH3 , ___ CH3CH2OCH2CH3 ,
___ CH3CHOHCH3 , ___ CH3COCH2CH3
28. Name the molecules in question 18.
29. Draw an example of keto-enol tautomerization. Names both forms.
30. 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
31. Draw the reaction of propanal with 2-propanol to create a hemi-acetal.
32. Name two ester-containing biological molecules.
33. Why are carboxylic acids more acidic than alcohols?