Name______________________

PUID______________________

CHM 25700
Exam #1
September 22nd, 2014

Any attempt at cheating (as judged by the proctoring TAs) will be dealt with
according to the policy regarding academic dishonesty in the course syllabus.
To submit an exam for re-grading, answers must be written in pen or have NO
eraser marks for questions to be re-graded. The exam must be returned to Mike
within one week of being returned to students in class.
You will be allotted 1 hour (60 minutes) to complete this exam. The exam
problems total of 100 + 10 (bonus) pts.
This exam contains a total of 10 pages (including a periodic table of
electronegativities and two blank pages attached to the end of the exam for
working out solutions).

I. a) Give correct names for the following compounds (historical-derived or IUPAC-derived

names). (2 x 4 pt).

b) Provide correct structures that correspond to the following names. (2 x 3 pts.)

c) The following names are incorrect. Provide the correct structures and IUPAC names for
these compounds. (2 x 6 pts)

d) Classify the following compounds as E or Z. (2 x 2 pts)

II. a) Draw Lewis structures for the two isomers with the molecular formula C2H6O. (6 pts)

b) Draw five (5) possible structures for C6H12 and name each one of them following the IUPAC
rules. You may draw the structures using the line-angle method. (15 pts)

c) Draw the most stable chair conformation for trans-1-tert-butyl-4-methylcyclohexane

(5 points)

III.) Draw in the missing starting material(s), reagent(s), or major product(s) as appropriate.
Indicate stereochemistry where necessary. If more than one correct answer is possible, give
only one of them. (3x4 = 12 points)

IV. a) Provide the pKas (2) for the indicated hydrogens of the following compounds.
(8 points)

b) Arrange these acids in order of increasing acidity. Put the letter of the weakest acid on the
left. You do not need to provide pKa values. (5 pts)

c) Define Lewis acid and Bronsted-Lowry acid. (5 pts)

V. a) Write the functional groups name and hybridization of the carbon atoms in the dotted
squares. (8 points)

A. Name________________________________________ Hybridization___________________
B. Name________________________________________ Hybridization___________________
C. Name________________________________________ Hybridization___________________
D. Name________________________________________ Hybridization___________________

b) Will the following reaction occur? Explain why or why not using pKa values. (6 pts)

VI. Write the structure of the major product and provide a mechanism of its formation using
complete arrow notation. (10 points)

(Answers written on this page will not be graded.)

(Answers written on this page will not be graded.)

(Answers written on this page will not be graded.)

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