WAYNE STATE UNIVERSITY SECOND EXAM February 22, 2011

CHEMISTRY 1030
Winter Term 2011 Page 1 (26 pts)
Page 2 (23 pts)
Name (print) KEY Page 3 (33 pts)
Signature Page 4 (18 pts)
TOTAL

I. On the line to the right of the compounds below, provide the IUPAC or common name for each of the follow-
ing compounds (2 points each), give its class (1 point), and circle the letter that best describes the compound
A=acidic, B=basic, N=neutral (1 point).

CLASS

1) (IUPAC) 3-bromo-3-methyl-2-phenylpentanal aldehyde N

2) (IUPAC) ethyl 2-chloropropanoate ester N

monosaccharide or
3) (common) glyceraldehyde aldehyde N

CH3
CH2

4) (common) dimethylethylamine amine B

CH3 N CH3

heterocycle or
5) (common) purine amine B

II. Below each of the following, draw the appropriate structure or answer the question.
6) Draw the structure of a diphosphate linked to 7) (3 pts) Show two resonance structures of any amide.
one methyl group (3 points). Amides are (circle one): neutral

O O
O
CH3 O P O P OH O

CH3 C N CH3 CH3 C N CH3

OH OH
H H
CHM 1030 Page 2 Name

8) Complete the equilibrium for the equation below, and give the name of the organic product. (3 points)

CH3 NH2 + H2O

CH3 NH3 OH

methylammonium ion or
methylammonium hydroxide

9) Draw the structure of acetic acid, circle the acidic hydrogen, and explain, using resonance structures,
why acetic acid is acidic. (4 points)
O
O O

CH3 C OH CH3 C O CH3 C O

The resonance structures stabilize the ionic structure by delocalizing the

negative charge.

10) Draw the structure of any thioester (3 points) 11) Draw the structure of any acetal. (3 points)

O CH3
O

CH3 C S CH3 CH3 C O CH3

III. For each of the following sets of compounds, circle the one that answers the question. (2 points each)
O

12) Which compound boils highest? CH3 C NH2

Cl O

13) Which compound is most soluble in water? CH2 C O Na

14) Which compound is most acidic? CH3 C OH

CH3

15) Which compound is most basic? CH3 CH NH2

CH3
16) Which compound contains a chiral carbon? Br
CH2 CH3
CHM 1030 Page 3 Name

IV. Answer each of the following questions:

17) Draw the mirror image of this Fischer projection 18) Draw the mirror image of this compound
(2 points) (2 points)

O O

CH CH OH OH
HO CH2 H2C OH
O O
HO H H OH

HO H H OH
OH OH
CH2 OH CH2 OH

19) Answer the following regarding the compounds shown above in questions 17 and 18 (2 points each).
a) How many chiral carbons are there in the compound shown in question 17? __2________
b) Is the compound shown in the answer part of question 17 D or L? __D________
c) The relationship between the question and answer shown in question 17 is (circle correct one)
enantiomers
d) Which biomolecule would the sugar shown in question 18 be found? __DNA_______
e) Is the sugar shown in question 18 a reducing or non-reducing sugar? ___reducing___________
20) The following questions deal with the disaccharide shown below (2 points each)
a) Circle the glycosydic linkage.
b) Circle the correct description of this bond
(1-4)
c) Circle the name of the monosaccharides in this sugar
glucose
d) The monosaccharide on the left is (circle correct answer): non-reducing
e) This disaccharide CANNOT (circle correct answer) be digested by humans.
V. Provide a definition or answer each of the following (3 points each):
21) neurotransmitter is a chemical that is released at the end of nerve cells that travels across
the gap to the next nerve cell as part of a nerve impulse.

22) oxidation reaction is the addition of an oxygen or the removal of hydrogens

23) Give the names of two types of starch found in plants and one type found in animals.

plant starches = amylose animal starch = glycogen

amylopectin
CHM 1030 Page 4 Name

VI. Draw the major organic product(s) for each of the following reactions (3 points each). If no reaction
occurs, write NR.

O OH
Ni
24) CH3 C + H2 CH3 CH

O OH

25) H

(hemiacetal)

O Br O Br

26) room temp.

CH3 C OH + CH2 NH2 CH3 C O CH2 NH3

O Br O Br

catalyst
27) CH3 C OH + CH2 NH2
heat
CH3 C NH CH2

O O

C O CH3 C O Na

28) + NaOH
+ CH3 OH

O O

29) heat + CH3 CH2 NH3

CH3 C NH CH2 CH3 + H2O + HCl CH3 C OH