As Usual, No Cheating Is Allowed. Good Luck

CHEMISTRY 1152

EXAM III

Summer, 2004

NAME______

All notes, books, etc., must be placed out of sight. Please read each of the problems carefully. If something is not clear, please ask.

The exam consists of 9 problems on 4 pages with some extra credit on the fourth page. Make sure your exam is complete. The exam is worth 100 points with each of the problems labeled as to its point value.

Answers should be placed in the space provided. Write legibly--if I cannot read it--it is wrong. Please include an explanation whenever asked to or whenever necessary to make your answer clear. Please put your name on every page of the exam.

As usual, no cheating is allowed. Good Luck!!! Chemistry 1152 2 Name______

1.(12) Name each of these structures correctly using systematic names… A. CH3 O B. O

H3C CH2 CH CH2 C H

NH 2 O C. D. H2C CH3 + H C H3C N CH2 CH3 _ O CH3

2.(12) Draw correct structures for each of the following… A. 4-chloro-5-methyl-2-hexanone B. ethanamide

C. amino acid in acidic solution D. any dipeptide

Extra Credit: I’m a bit of a popcorn junkie, but I love it smothered with butter or butter flavoring. Butanedione is the flavor of butter used in many popcorns. Draw it here: Chemistry 1152 3 Name______

3.(30) Complete the following reactions. If no reaction occurs, write NO REACTION. O H+ A. C + H3C CH2 OH H

B. The product of “A” + CH3OH

O Δ C. H3C CH2 NH2 + H3C CH2 C OH O KMnO4 CH2 C D. H

E. H3C CH2 NH2 + H3C CH2 C OH

O  F. + H Ni H3C C CH3 2

O You supply correct reactants H C C CH CH and conditions G. 3 2 3

NaOH H. CH3CH2NH2 + CH3Cl

H2C OH H2C OH Δ I. O O H H+ OH OH + H2O O OH OH OH OH Maltose

O H2O Solution J. H3C CH C Neutral NH2 OH Chemistry 1152 4 Name______

4.(8) The molecule on the left is a partial H2C OH H2C OH drawing of galactose and the molecule on the right is a partial HO O O drawing of glucose. OH OH a) When these two molecules are linked together they form a disaccharide called lactose, a sugar found in OH OH dairy products. Create lactose by connecting the two molecules with a 1-4 bond. b) Create the alpha isomer by placing the –OH group on the glucose part of the molecule that completes the hemiacetal group thus making -lactose. c) Would your new molecule be a reducing sugar? d) Some people lack the enzyme necessary to hydrolyze this molecule. Draw an arrow () to indicate where the site of hydrolysis would occur if you have the proper enzyme.

5.(15) There are four amine isomers with the formula C3H9N. Draw three, name them, and indicate whether each is primary, secondary or tertiary. 1. 2. 3.

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6.(5) How does denaturation of a protein differ from hydrolysis of a protein?

7.(5) Draw: (NH2) Ser  Ala  Leu  Val (COOH)

8.(8) Remember how much fun multi-step reactions were. Try ONE of these: Chemistry 1152 5 Name______

A. Use propene to make propanone B. Use butanal to make butanone

9.(5) Many amine containing drugs are given to patients in their salt form, such as hydrochloride or sulfate. What might be the reason for this?