1. 4-methyl-4-octanol oxidizes to form
a) 4-methyl-4-octanal
b) 4-methyl-4-octanone
c) butyl butanoate
d) none of the above
2. The reduction of pentanal yields
a) 1-pentanol
b) 2-pentanol
c) pentene
d) pentane
3. The oxidation of 2-methyl-3-hepatanone yields
a) 2-methyl-heptanol
b) 2-methylheptanal
c) 2-methyl-3-heptanol
d) none of the above
4. Identify how many chiral carbons are in the following molecule
a)
b)
c)
d)
4
3
2
8
5. Tertiary alcohols can react to form
a) aldehydes
b) ketones
c) ethers
d) no reaction
6. What is the molecular formula for 3-methyl-2-hexanone
a) C6H12O
b) C7H14O
c) C7H16O
d) C6H14O
7. Which of the following will have the highest boiling point?
a) 2-hexanone
b) 2-hexanol
c) hexanal
d) hexane
8. What is the name of the reaction between an alcohol and an aldehyde?
a) oxidation
b) reduction
c) addition
d) none of the above
9. What determines if a molecule is a reducing sugar?
a) It has an anomeric –OH available
b) It is a monosaccharide
c) It is a disaccharide
d) It must be a beta linkage
10. What is the name of the enzyme that cleaves the glycosidic bond in lactose?
a) lactese
b) lactase
c) sucrose
d) galactase
11. Sucrose is composed of which of the following monosaccharides.
a) glucose
b) galactose
c) fructose
d) A and C
12. Which of the following molecules have the formula C6H12O
a) 2,3-dimethylpentanal
b) 3-methylhexanal
c) 2-methyl-3-pentanone
d) 2-methyl-cyclohexanone
13. Primary alcohols reduce to form
a) aldehydes
b) ketones
c) ethers
d) no reaction
14. In the following carbohydrate, identify the linkage
a)
b)
c)
d)
alpha-1, 3
beta-1, 4
alpha-1, 4
beta-1, 3
15. Disaccharides are formed from ______. Polysaccharides are formed from _____.
a) rehydration, condensation
b) addition, condensation
c) condensation, reduction
d) condensation, condensation
16. The following are aldoses except:
a) fructose
b) glucose
c) galactose
d) none of the above
17. A furanose is ___. _____ forms a furanose.
a) 5-membered ring, glucose
b) 6-membered ring, glucose
c) 5-membered ring, fructose
d) 6-membered ring, galactose
18. Which polysaccharide uses 1,4-beta linkages?
a) amylose
b) amylopectin
c) cellulose
d) glycogen
19. The carbonyl can make _______ hydrogen bonds.
a) 0
b) 1
c) 2
d) 3
20. Aldehydes ____ soluble in water. Carboxylic acids ______ soluble in water
a) are, are not
b) are not, are not
c) are, are
d) are not, are
21.Of the following, which would have the highest boiling point?
a) propane
b) propanal
c) propanoic acid
d) methyl ethyl ether.
22. Of the following aldehydes, which is most soluble in water
a) methanoic acid
b) ethanoic acid
c) propanoic acid
d) pentanoic acid
23. Carboxylic acids can be oxidized to form
a) aldehydes
b) primary alcohols
c) none of the above
d) A and B
24. When you add one alcohol across a carbonyl you form
a) aldehydes
b) ketones
c) acetals
d) hemiacetals
25. Base catalyzed ester hydrolysis:
a) is called saponification
b) yields carboxylic acid
c) is called reverse esterification
d) yields carboxylate cation
26. When you add two alcohols across a carbonyl you form
a) acetals
b) hemiacetals
c) ketones
d) aldehydes
27. Ketones and aldehydes are
a) structural isomers
b) enantiomers
c) stereoisomers
d) configurational isomers
28. Carbonyl groups are bonded to ___ carbons and ____ hydrogens in ketones.
a) 1, 1
b) 1, 0
c) 0, 0
d) 0, 1
e) 2, 0
29.Carbonyl groups are bonded to __ carbons and ___ hydrogens in aldehydes
(except formaldehyde).
a) 0, 1
b) 0, 0
c) 1, 0
d) 1, 1
30. Secondary alcohols are reduced to
a) ketones
b) aldehydes
c) ethers
d) no reaction
Short Answer
31. Draw and name 6 ketones, aldehydes or alcohols with the formula C9H18O.
O
H2
C
O
C
H
H2
C
C
H2
H2
C
C
H2
H2
C
H2
C
C
H2
CH3
H3 C
CH3
CH3
H2
C
C
H2
H2
C
C
H2
H2
C
C
H2
H3 C
H3 C
H2
C
CH
H2
C
C
H2
CH3
nonanal
3,3-dimethyl-2-heptanone
2-nonanone
CH3
C
H2
H2
C
CH
CH3
O
H3 C
C
CH3 H2
CH3
O
H3 C
H2
C
C
H2
O
CH2
H2
C
CH
H3 C
H2
C
CH3
CH
CH3
O
CH3
C
H2
2-methyl-3-octanone
3-methyl-2-octanone
4, 5-dimethyl-2-heptanone
32. Draw and name the products for the following reactions
a. Oxidation of 2-pentanol
O
H2
C
H3 C
C
H2
CH3
2-pentanone
b. Reduction of 2-ethyl-3-octanone
H3 C
CH2
H2
C
CH
H3 C
H2
C
C
H2
CH3
C
H2
O
Actual proper name:3-methyl-4nonanone
c. Oxidation of 2,3-dimethyl-3-heptanol
NO REACTION
33. Given the following structure of allose
1. Number the carbons and label the anomeric carbon.
2. Draw the Fischer projection.
3. Is this alpha or beta allose?
4. Draw a 1, 4-alpha linkage between two of these allose molecules.
O
CH
H
OH
H
OH
H
OH
H
OH
H2 C
OH
alpha allose
HO
CH2
HC
HO
O
H
C
HC
CH2
HC
H
C
O
H2 C
CH2
CH2
O
HC
OH
OH
CH
OH
34. Describe the boiling point behaviors of aldehydes and ketones as compared to
alcohols, ethers, carboxylic acids and alkanes.
Aldehydes and ketones have lower boiling points than alcohols and carboxylic acids
and higher boiling points than ethers and alkanes.