1529 Ucf Prof Elsheimer Exam 4 Review

UCF - ORGANIC CHEMISTRY 2 - PROF.
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: Determine the reagent(s) necessary to complete the reaction below.
PRACTICE: Draw (with curved arrows) a mechanism for the following reaction:
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PRACTICE: Which product is formed from the following transformation?
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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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PRACTICE: What is the predominant product from the reaction of 2-hexanol with PCC in CH2Cl2?
PRACTICE: What is the major product of the following rxn:
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PRACTICE: What is the major product of the following reaction?
a.I
b. II
c. III
d.IV
e. None of the above
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PRACTICE: Assign both IUPAC and COMMON names to the following structures.
PRACTICE: Give the IUPAC name for the following structure.
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PRACTICE: Draw the structure for (2R,4S,5E,8S)-4-amino-8-chloro-2-hydroxy-7,9-dioxonon-5-

enoic acid
PRACTICE: Place the following compounds in order of their acidity with #1 being the most acidic
and #5 being the least acidic.
PRACTICE: Which is the strongest acid?
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PRACTICE: Rate the following compounds from least acidic (number 1) to most acidic (number 3).
PRACTICE: Predict the product of the following reaction:
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PRACTICE: Give the IUPAC nomenclature of the following molecule. Include appropriate
designations for geometric and chirality.
PRACTICE: Draw a structural formula for the following molecule.
(3S, 4S)-3-Chloro-4-methylhexanoyl chloride
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PRACTICE: Give the IUPAC name for the following structure.
PRACTICE: Determine the reagent(s) necessary for the reaction below.
PRACTICE: Determine the reagent(s) necessary for the reaction below.
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PRACTICE: You are going to have to think about this one! The following pKa values will help in
your analysis:
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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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PRACTICE: Determine the necessary reagent and provide the mechanism for the reaction below.
PRACTICE: Rank in order of decreasing reactivity in toward nucleophilic addition-elimination.
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PRACTICE: Provide the product for the following reaction.
PRACTICE: Predict the product(s) formed in the following reaction.
PRACTICE: What are the product(s) formed from the following reaction?
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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?
a) PhNHCH2Ph (Ph = phenyl)
b) Diphenylamine
c) Dibenzylamine
d) N-Phenylbenzamide
e) None of the above
PRACTICE: Provide a mechanism for the following reaction.
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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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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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PRACTICE: For the following scheme, draw the structures for X and Y.
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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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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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PRACTICE: Which is not an intermediate in the hydrolysis of a nitrile?
PRACTICE: Provide a mechanism for the acid promoted hydrolysis of benzonitrile to benzoic acid.
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PRACTICE: Provide a complete mechanism for the following transformation.
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PRACTICE: Draw the principal organic product in the box provided.
PRACTICE: Provide a detailed mechanism for the following reaction. All arrows and structures of
intermediates must be clearly indicated.
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PRACTICE: Provide a mechanism for the following reaction.
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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PRACTICE: Write out the mechanism for the following transformation.
PRACTICE: How many tautomers can you draw?
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PRACTICE: Draw the enol tautomer for the following ketone:
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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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.
PRACTICE: What would be the major product of the following reaction?
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PRACTICE: Which of the following are the best conditions for the following transformation?
A. NaCl, HCl, SOCl2 in CH2Cl2
B. Cl2, NaOH, H2O
C. Cl2, AcOH
D. PCl3, HOCH2CH2OH
E. NaBH4, PCl3
PRACTICE: Provide a detailed mechanism for the following transformation.
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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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PRACTICE: Which electrophile will give the best enolate alkylation?
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PRACTICE: What is the product of this synthesis?
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PRACTICE: Propose a mechanism for the following reaction.
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PRACTICE: The final product of the following synthesis is:
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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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PRACTICE: Which of the following compounds will undergo decarboxylation (loses CO2) upon
heating to 100°C?
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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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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
e) All of the above will work.
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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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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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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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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PRACTICE: Provide a detailed mechanism for the following transformation.
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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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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PRACTICE: Show how one could use the Stork enamine synthesis to carry out the following
transformation.
PRACTICE: Draw the intramolecular condensation product formed when 2,6-heptanedione is

heated with aqueous sodium hydroxide.
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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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UCF - ORGANIC CHEMISTRY 2 - PROF.

PRACTICE: Determine the reagent(s) necessary to complete the reaction below.

PRACTICE: Which product is formed from the following transformation?

PRACTICE: What is the major product of the following rxn:

PRACTICE: What is the major product of the following reaction?

e. None of the above

PRACTICE: Give the IUPAC name for the following structure.

PRACTICE: Draw the structure for (2R,4S,5E,8S)-4-amino-8-chloro-2-hydroxy-7,9-dioxonon-5-

PRACTICE: Which is the strongest acid?

PRACTICE: Predict the product of the following reaction:

PRACTICE: Draw a structural formula for the following molecule.

(3S, 4S)-3-Chloro-4-methylhexanoyl chloride

PRACTICE: Give the IUPAC name for the following structure.

PRACTICE: Determine the reagent(s) necessary for the reaction below.

PRACTICE: Determine the reagent(s) necessary for the reaction below.

PRACTICE: Rank in order of decreasing reactivity in toward nucleophilic addition-elimination.

PRACTICE: Provide the product for the following reaction.

PRACTICE: Predict the product(s) formed in the following reaction.

a) PhNHCH2Ph (Ph = phenyl)

e) None of the above

PRACTICE: Provide a mechanism for the following reaction.

PRACTICE: Which is not an intermediate in the hydrolysis of a nitrile?

PRACTICE: Provide a complete mechanism for the following transformation.

PRACTICE: Draw the principal organic product in the box provided.

PRACTICE: Provide a mechanism for the following reaction.

PRACTICE: Write out the mechanism for the following transformation.

PRACTICE: How many tautomers can you draw?

PRACTICE: Draw the enol tautomer for the following ketone:

PRACTICE: What would be the major product of the following reaction?

A. NaCl, HCl, SOCl2 in CH2Cl2

B. Cl2, NaOH, H2O

PRACTICE: Provide a detailed mechanism for the following transformation.

PRACTICE: Which electrophile will give the best enolate alkylation?

PRACTICE: What is the product of this synthesis?

PRACTICE: Propose a mechanism for the following reaction.

PRACTICE: The final product of the following synthesis is:

e) All of the above will work.

PRACTICE: Provide a detailed mechanism for the following transformation.

PRACTICE: Draw the intramolecular condensation product formed when 2,6-heptanedione is

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