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Honor Code: I have neither given nor received unauthorized aid on this exam. I understand that I am not allowed to use any calculator, notes, books, or resources (other than molecular models). I also understand that removal of the exam from the testing room or receiving aid from any other person or other person's exam constitutes an honor code violation. I also understand that making any change to an exam answer post-grading with the intent of submission for regrading is an honor code violation. Signature: _____________________________PID#__________________ Please clearly print your last name:________________________________

Chemistry 261 Spring 2010 Exam 3 Ashby

Part I. Part II. Part III. Part IV.

Nomenclature Reactions/Synthesis Mechanisms Short Answer TOTAL

_______________ (12 points possible) _______________ (44 points possible) _______________ (28 points possible) _______________ (16 points possible) _______________ (100 points possible)

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I. Nomenclature (12 points) Write a correct name (IUPAC or common as indicated) for each of the following. (IUPAC name) C. (Common name)
Br

A.

HO

OH

D. B. (Common name) CHCl3

(IUPAC name)
HO

II.

Reactions/Synthesis (44 points). Complete the following reactions by giving the missing reagent(s), starting material(s) or product. Include appropriate solvents.

A.

B.

Br

NH3 (substitution product only)

C.

Cl

CH3CH2OH (elimination product only)

D.

HO

HCl, ether

NBS, h, CH2Cl2 E.

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KO F. I HO

H G. H3CH2C CH3 Br H

CH2CH3

NH 2 NH3 (Draw product with correct stereochemistry)

Problems H. and I. may require more than one step! H. O OH

OH I. R stereoisomer

SCH3

S stereoisomer

III.

Mechanisms (28 points) A. For the following reaction, draw the indicated steps.

Cl2 , heat

Cl
Rate Determining Step:

Termination by Disproportionation:

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B. Write a detailed, stepwise mechanism for the following reaction.

OH

SOCl2, NH3

Cl

C.

Write a detailed, stepwise mechanism for the following reaction.

OH
H3 O+

H3O+

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IV. A. Short Answer (16 points) Circle the compound with the lowest boiling point?

A.
Br

B.
Cl

C.
F

Briefly explain: ___________________________________________________________________________________

B.

What are the two factors that affect the polarity of an alkyl halide? 1) mass and density 2) mass and bond strength 3) bond length and bond strength 4) bond length and electronegativity

C.

Place the following in order of decreasing boiling point. (Highest boiling point = 1; Lowest boiling point = 3) 1) CH3Cl
_______________

2) CH3OH
_______________

3) CH4
_______________

D.

Which is an accurate statement of Hammonds postulate? 1) The transition state of an exothermic reaction will resemble the starting material more than the product. 2) The transition state of an exothermic reaction will resemble the product more than the starting material. 3) The transition state of an endothermic reaction will resemble the starting material more than the product. 4) The difference in energy between the starting material and the transition state controls the rate of reaction.