1. 4-Methyl-4-Octanol Oxidizes to Form

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) 4 b) 3 c) 2 d) 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) alpha-1, 3 b) beta-1, 4 c) alpha-1, 4 d) 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.

H 2 H 2 H H H H O 2 2 2 2 C C C C C C H 3 C C C H 3 C C C C C H H 3 C H 3 2 H H 2 H 2 H 2 C H 3

O C H 3 H H H 2 H 2 H 2 2 2 C C C C H C C C H 3 H C C C H 3 C C C C C H 3 3 H H H 2 H 2 H 2 2 2 O O H 3 C C H 2 H H 2 H 2 2 C H C C H C C C H 3 3 H C C H H 3 C C H C C 3 H 2 H 2 C H O C H 3 3 nonanal 3,3-dimethyl-2-heptanone 2-nonanone 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

H 2 C H 3 C C C H 3 H 2 2-pentanone

b. Reduction of 2-ethyl-3-octanone

H 3 C C H 2 H 2 H 2 C H C C C H 3 H 3 C C C H 2 H 2 O Actual proper name:3-methyl-4- nonanone

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 C H

H 2 C O H alpha allose

H O C H 2 H O C H 2

H C O H C O H H H C C C C H 2 O O HH C C H H 2 C C H 2

O H O H

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.