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ELSHEIMER
UCF PROF. ELSHEIMER EXAM 4 REVIEW
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Draw (with curved arrows) a mechanism for the following reaction:
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Complete the mechanism for the following oxidation of an aldehyde reaction. Draw all
the arrows to indicate movement of electrons, write all lone pairs, all formal charges, and all the
products for each step. In the dotted box write which mechanistic element is involved in each step.
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: What is the predominant product from the reaction of 2-hexanol with PCC in CH2Cl2?
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
a.I
b. II
c. III
d.IV
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Assign both IUPAC and COMMON names to the following structures.
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Place the following compounds in order of their acidity with #1 being the most acidic
and #5 being the least acidic.
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Rate the following compounds from least acidic (number 1) to most acidic (number 3).
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Give the IUPAC nomenclature of the following molecule. Include appropriate
designations for geometric and chirality.
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: You are going to have to think about this one! The following pKa values will help in
your analysis:
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Place the following molecules in order of their reactivity under base-catalyzed
nucleophilic addition-elimination conditions. Label the most reactive as #1 and the least reactive as
#5.
PRACTICE: Draw the major product(s) for the following reaction. Assume the nucleophile is
in excess. If there will be no reaction, write NR.
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Determine the necessary reagent and provide the mechanism for the reaction below.
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: What are the product(s) formed from the following reaction?
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Predict the major product for the following reaction, paying attention to the regio- and
stereochemistry where appropriate.
PRACTICE: What is the result of treating benzoyl chloride with aniline followed by LiAlH4 then
water?
b) Diphenylamine
c) Dibenzylamine
d) N-Phenylbenzamide
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Which of the following is (are) tetrahedral intermediate(s) in the acid catalyzed
esterification of benzoic acid with ethanol?
PRACTICE: Provide a detailed reaction mechanism for the following transformation. This is an
intramolecular version of what type of reaction?
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Complete the mechanism for the following acid catalyzed ester hydrolysis reaction. Be
sure to show arrows to indicate movement of all electrons, write all lone pairs, all formal charges,
and all the products for each step. IF A NEW CHIRAL CENTER IS CREATED IN AN
INTERMEDIATE OR THE PRODUCTS, MARK IT WITH AN ASTERISK AND LABEL AS
"RACEMIC" IF RELEVANT. IN THE BOX BY EACH SET OF ARROWS, WRITE WHICH OF THE 4
MECHANISTIC ELEMENTS IS INDICATED IN EACH STEP OF YOUR MECHANISM (For
example, "Add a proton").
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: For the following scheme, draw the structures for X and Y.
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: A nitrile is prepared from the corresponding primary amide by reaction with which of
these?
a) HCl
b) Cl2
c) P4O10
d) HOCl
e) AlCl3
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Provide a mechanism for the following transformation. Show all important flows of
electrons, charges and intermediates. Where indicated, (in the structure-n-a- box)-draw the
intermediates.
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Provide a mechanism for the acid promoted hydrolysis of benzonitrile to benzoic acid.
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Provide a detailed mechanism for the following reaction. All arrows and structures of
intermediates must be clearly indicated.
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Show to how synthesize from the starting molecule (indicated as SM) to yield the
target molecule (indicated as TM) below.
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Please give the pKa of the MOST ACIDIC proton for the molecule below.
a) 5
b) 10
c) 12
d) 20
e) 45
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Each of the following undergo the process of tautomerization. For each draw the other
major tautomer, then for each pair, circle the one that is more stable.
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Which of the following are the best conditions for the following transformation?
C. Cl2, AcOH
D. PCl3, HOCH2CH2OH
E. NaBH4, PCl3
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Show the reagent(s) and/or condition(s) one could use to carry out the following
transformation. More than one step may be required.
PRACTICE: What would be the major product of the following reaction sequence?
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Alkylations of the enolate of ketone A produce almost exclusively the dialkylation
product, as shown below. Demonstrate how you would use an enamine to prepare monoalkylated
ketone B.
PRACTICE: Which acid derivative shown below would NOT undergo decarboxylation upon
heating?
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Which of the following compounds will undergo decarboxylation (loses CO2) upon
heating to 100°C?
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Which is the major product formed for the reaction below?
PRACTICE: Draw the structural formula, including stereochemistry when necessary, of the
organic product(s) for the following reaction.
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Which combination of starting materials would react with catalytic NaOEt to produce a
product?
a) B and E
b) B and C
c) A and C
d) C and D
PRACTICE: Complete the following reactions by drawing the structures of the principal major
products in the box shown. Indicate relative stereochemistry where necessary. If there is no
reaction, write NR.
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Show the reagent(s) and/or condition(s) one could use to carry out the following
transformation. More than one step may be required.
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Using any reagents turn the starting material into the indicated product. All carbon
atoms must come from the starting material. Draw all molecules synthesized along the way. When
in doubt, draw the molecule! Label all chiral centers with an asterisk (*) and make sure to right
"Racemic" where appropriate. Hint: this should look familiar as a homework problem. Remember,
all of the carbons of the product must come from the given starting material.
PRACTICE: Identify the starting aldehyde or ketone needed to make each of the following
compounds via an aldol condensation
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: List the reagents A-D in the order necessary to complete the following transformation.
PRACTICE: Provide an unambiguous structural formula for the condensation product expected
when the compound below is treated with sodium ethoxide, then quenched with cold dilute aqueous
acid.
PRACTICE: Predict the product(s) in the following aldol condensation using aqueous sodium
hydroxide.
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Fill in the roles (abbreviated in parentheses) of the reactants in the boxes.
Which one is the Michael donor ( D)? Which one is the Michael acceptor ( A)?
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Indicate the order in which the intermediates would appear during the conversion of 1
into 2. The asterisk (*) in the answers indicates the step where the quench is used.
a) 1 → III – * → II → 2
b) 1 – * → IV → II → 2
c) 1 → II – * → 2
d) 1→ II → I – * → 2
e) 1 → V → III – * → 2
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Show how one could use the Stork enamine synthesis to carry out the following
transformation.
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UCF - ORGANIC CHEMISTRY 2 - PROF. ELSHEIMER
PRACTICE TEST: UCF PROF. ELSHEIMER EXAM 4 REVIEW
PRACTICE: Provide both the reagents (in square boxes) and the product (rounded box) for these
synthesis. (Note, that a second reagent may be required in the square boxes. For example, the acid
step of a Grignard addition.) In the rounded rectangle, draw the structure of the compound from the
first reaction.
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