CHM 2210-01(02-10) Example 2 of OLD Examination 3

INSTRUCTIONS (Read carefully): Carefully separate all sheets. This examination has 2 pages of problems, 1 double-
sided answer sheet, a periodic table, and 1 blank sheet for scratch work. Read each question carefully. For 2 bonus points,
correctly complete as requested on both sides of the answer sheet: print your name, sign your name, give your Canvas login user
name, give your row letter and seat number, and give your Discussion Section number. Put your answers in the spaces provided
on the answer sheet. Only answers on the answer sheets will be graded. Only the answers sheet will be collected. There is a total
of 100 points plus 2 bonus points. Before the next lecture, go over problems about which you were not confident on this
examination and make your own answer key.
REGRADE POLICY: If you have a question about the number of points that you earned on your graded exam answer
sheet, do not make changes or additions to your returned, graded answer sheet. Write on a separate sheet of paper what items
you believe that you were not given sufficient credit and the reasons why you think so. Attach it to your original answer sheet
and give it to Dr. Hilinski after a lecture or during an office hour, preferably within 2 weeks after it is returned. Be sure to make
and keep a photocopy for your records.

1. [9 points] For the compound given to the right, provide a name. It is a single pure
stereoisomer. Be sure to designate configurations (R, S, E, and Z) properly.

2. [14 points] For each of the following, provide a structural formula. Be sure to identify stereoisomers properly.
You may give any acceptable type of structural formula, unless otherwise specified.
(a) (S)-1-methylpentyl p-toluenesulfonate (b) (R,Z)-5-bromo-3,6-dimethylhept-3-ene (c) pyridine

3. [17 points] Using arrows to show the flow of electrons, give a

stepwise mechanism for the transformation shown to the
right. Clearly show stereochemistry for each elementary step
in the mechanism.

4. [12 points] For each of the following transformations, provide an efficient multistep synthesis for the conversion of the
given starting material into product. Each transformation requires at least two reactions. For each functional group
transformation, give all necessary conditions (reagents, catalysts, and other reaction conditions) and give a structural
formula of the organic product. For all organic compounds, give structural formulas; do not give abbreviations or names.
Show stereochemistry appropriately when necessary. If a mixture of products must be present after a step, show the mixture
and circle the one that you need to take forward to the next step.

5. [14 points] For each of the following, choose the best answer; give the letter.
(i) Which reaction is not a concerted reaction:
(a) bromocyclopentane with NaI in acetone; (b) 3-bromopentane with NaOCH3 in CH3OH; or
(c) (R)-2,2-dimethylcyclopentanol heated with concentrated H2SO4?
[RECALL: A reaction that has more than one transition state linking overall reactants with overall products is not a concerted
reaction.]
(ii) Does the reaction of (R)-2-bromopentane with NaN3 occur faster in: (a) dimethyl sulfoxide or (b) ethanol?
(iii) When 1-hexanol is added to water, is 1-hexanol: (a) the top layer; (b) the bottom layer; or
(c) neither the top nor the bottom layer because it is miscible with water ?
(iv) Which reaction with sodium iodide in acetone is faster:
(a) cyclohexyl bromide or (b) cyclohexyl p-toluenesulfonate?
(v) The reaction of (R)-2-bromopentane with KOC(CH3)3 in (CH3)3COH gives the major product that is formed via which
one of the following mechanisms: (a) SN1 ; (b) SN2 ; (c) E1; or (d) E2?
(vi) Which one of the following is thermodynamically less stable:
(a) (E)-cyclotetradecene or (b) (Z)-cyclotetradecene?
(vii) Which one of the following is soluble in acetone:
(a) sodium chloride; (b) sodium bromide; (c) sodium iodide; or (d) sodium p-toluenesufonate?
CHM 2210-01(02-10) Example 2 of OLD Examination 3 (Page 2)
6. [10 points] Each of the following (intermediate or transition-state structure) is involved in the mechanism of one or more of
the organic chemical reactions that we
have covered.

For each part (a & b), select an organic reaction in which the given intermediate or transition-state structure is
involved and give a chemical equation for your selected organic reaction that includes the following in each of
your answers:
(i) structural formula(s) for the organic reactant(s) [Be sure to show stereochemistry clearly when necessary.];
(ii) a structural formula for the major organic product [Be sure to show stereochemistry clearly when necessary.]; and
(iii) the experimental conditions (Give structural formulas for organic compounds. Give a chemical formula
for inorganic reactants or catalysts . If heat and/or light is needed, be sure to indicate it appropriately.)
As we do for most organic reaction equations, the chemical equations that you give do not need to be
balanced. Be sure to show stereochemistry clearly when necessary.

EXAMPLE: For the involvement of in an organic chemical reaction, here is an

acceptable answer.

7. [24 points] For each part (a-h) shown below, supply a structural formula for the major organic product(s) when the
product(s) is(are) not given; if no reaction occurs, write N.R.
IMPORTANT: If the major product is a mixture of stereoisomers (such as a mixture of enantiomers or a mixture of
diastereomers), give a structural formula for each of the stereoisomers in the mixture. ALSO, write equal if equal amounts
of stereoisomers are formed or unequal if unequal amounts of stereoisomers are formed.
Provide the following when a product is given. If an organic reactant is missing, supply a structural formula; if an
inorganic reactant (reagent) or catalyst is missing, simply give a formula. If heat and/or light is needed, be sure to indicate it
appropriately if these conditions are missing. If more than one reaction step is needed, be sure to put
1. … and
2. … (etc.) as needed.
Give the best possible answers. For all organic compounds, give structural formulas; do not give abbreviations or
names. Be sure to show stereoisomers properly when necessary.
CHM 2210 PRINTED NAME: ________________________________________ Disc. Sec. No. _____
FSU Email Address Example 2 of OLD EXAMINATION 3
before @ OR
Canvas login
User Name ________ @ ROW ____ SEAT ____ SIGNED NAME: _______________________________________
INFO[2] 1 [9] 2 [14] 3 [17] 4 [12] 5 [14] 6 [10] 7 [24] TOTAL [102]

1) (E,R)-7,7-divinylcyclooct-4-en-1-ol

2a) 2b) 2c)

3)
CHM 2210 PRINTED NAME: ________________________________________ Disc. Sec. No. _____
FSU Email Address Example 2 of OLD EXAMINATION 3
before @ OR
Canvas login
User Name ________ @ ROW ____ SEAT ____ SIGNED NAME: _______________________________________
4a)

4b)

5i) 5ii) 5iii) 5iv) 5v) 5vi) 5vii)

6a) iii 6b) iii

i → ii i → ii

7a) 7b) 7c) 7d)

7e) 7f) 7g) 7h)