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TEXAS - ORGANIC CHEMISTRY I - PROF.

COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

www.clutchprep.com
* This review was not prepared by your professor or school and is neither approved nor endorsed by your college or university 1
TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Which one of the following best represents the shape of δ* anti-bonding molecular
orbital?

SUMMARY: Formal Charges

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: In which of the following molecules would the net charge be equal to zero?

A. I

B. II

C. III

D. IV

E. More than one of these

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Look at the entire structure of Atenolol. What is the total number of lone pairs
present within the structure of this molecule?

A. 0

B. 1

C. 2

D. 3

E. 4

F. 5

G. 6

H. 7

I. 8

J. None of these

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Look at the entire structure of Lamisil. How many hydrogen atoms are present in the
structure of this molecule?

A. 20 E. 24 I. 28

B. 21 F. 25 J. None of these

C. 22 G. 26

D. 23 H. 27

PRACTICE: Construct a Lewis structure for NO 2F. Include all nonbonding electrons and formal
charges.

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

SUMMARY: Resonance Structures

PRACTICE: Draw three other important resonance contributors for the molecule below.

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: VSEPR theory predicts an identical shape for all of the following,except: (hint: draw
the Lewis structures before deciding )

a. OCl3+

b. Br2CO

c. CH3●

d. Et2O

e. All have the same geometry

f. none of the above

SUMMARY: Hybridization

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Indicate the hybridization for carbon a,b,c and d.

a. ____________ b. _____________

c. ____________ d. _____________

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Draw a picture, give an example, or define to explain each of the following terms.

tert-butyl nucleophile

secondary carbocation dialkyloxonium ion

2° amine phenyloxonium ion

pKa benzyl halide

H-Bond nitrile

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: What is the total number of sigma (σ) bonds present within the structure of N 2F2?

A. 1

B. 2

C. 3

D. 4

E. 5

F. More than 5

PRACTICE: Use line-angle (skeletal) structures (showing all lone pairs).

A. Create the electron arrows needed to arrive at the other resonance structures for the following
molecules.

B. Construct the new resonance structure produced by that shift in electrons.

C. Classify each of them as major or minor contributors to the resonance hybrid.

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

SUMMARY: Functional Groups

PRACTICE: Identify ALL of the functional groups in the following molecule. Assign degree of
functional group when appropriate.

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

SUMMARY: IUPAC Naming

PRACTICE: Draw the structure described by this name: 2-Ethyl-3-methylpentane

Which statement below is TRUE?

A. The name 2-ethyl-3-methylpentane is CORRECT

B. The correct name of this molecule is 3,4-dimethylhexane

C. The correct name of this molecule is 4-ethyl-3-methylpentane

D. The correct name of this molecule is 2,4-dimethylhexane

E. No statement above is true

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

SUMMARY: Alkyl Groups

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: For the two questions below, an incorrect name has been given for an alkane. To
answer these questions, you will need to draw the structure described by the incorrect name. Once
you have drawn the structure, use the nomenclature rules to assign the correct name to the alkane.

The incorrect name is: 2-Methyl-5-tert-butylheptane What is the correct name of this alkane?

A. 5-Ethyl-2,6,6-trimethylheptane

B. 3-Ethyl-2,2,6-trimethylheptane

C. 5-tert-Butyl-2-methylheptane

D. 4-tert-Butylisooctane

E. None of the above

The incorrect name is: 4-Butyl-2,2-dimethyloctane What is the correct name of this alkane?

A. 5-Butyl-7,7-dimethyloctane

B. 2,2-Dimethyl-4-butyloctane

C. 5-Neopentylnonane

D. 5-tert-Butylnonane

E. None of the above

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Determine the IUPAC name for the structure given below.

a) 1-methyl-4-ethyl-1-pentanol

b) 1,4-dimethyl-1-hexanol

c) 3-methyl-6-heptanol

d) 5-methyl-2-heptanol

PRACTICE: Which structure shown below represents ( Z )-3,5-dichloro-3-hexen-1-yne?

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Determine the IUPAC name for the compound given below.

a) ortho-bromocyclohexanol

b) endo-2-bromocyclohexanol

c) cis-2-bromocyclohexanol

d) trans-2-bromocyclohexanol

SUMMARY: Degrees of Unsaturation

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Which of the following compounds have the same degree of unsaturation?

a.I & II
b.I & III
c.III & IV
d.II & III
e.I & IV

SUMMARY: Constitutional Isomers

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Which one of the following compound(s) is constitutional isomers of spiro[2.2]pentane?

SUMMARY: Intermolecular Forces

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Which of these compounds would have the highest boiling point?

a. I

b. II

c. III

d. IV

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Select the molecule with greater solubility in water. Provide a brief explanation.

Propanoic acid or Decanoic acid

SUMMARY: Drawing Newman Projections

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Draw the lowest and the highest energy Newman Projection looking down the C1-C2
bond for 1-bromo-2-methylpropane.

PRACTICE: What is the total strain energy (in kcal/mol) of the least stable (highest
energy) conformation possible for 2,3-dimethylbutane? All of the choices below are expressed in
units of kcal/mol.

A. 0 B. 0.9 C. 1.8 D. 2.7 E. 3.4

F. 3.6 G. 4.4 H. 5.8 I. 7.2 J. None of these

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Draw the bond-line structure for the following compound.

PRACTICE: For the pair of molecules drawn below, choose the letter that corresponds to the
MORE STABLE molecule.

Does the UNSTABLE molecule chosen below have ANGLE STRAIN?

Does the UNSTABLE molecule chosen below have TORSIONAL STRAIN?

Does the UNSTABLE molecule chosen below have STERIC STRAIN?

* This review was not prepared by your professor or school and is neither approved nor endorsed by your college or university 22
TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: For the pair of molecules drawn below, choose the letter that corresponds to the
MORE STABLE molecule.

Does the UNSTABLE molecule chosen below have ANGLE STRAIN?

Does the UNSTABLE molecule chosen below have TORSIONAL STRAIN?

Does the UNSTABLE molecule chosen below have STERIC STRAIN?

PRACTICE: Consider (1S, 3R)-1,3-dimethylcyclohexane. Draw the two chair conformations and
determine which conformation is more stable.

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: A conformation for a cyclohexane derivative is shown below. Calculate the interaction
energy for this form. Show calculations.

_______________________________________________ kcal/mol

What is the name of this form? _______________

Interaction Energy Table:

Interaction Energy (kcal/mol)

H:H eclipsed 1.0


CH3:H eclipsed 1.4
-CH- : -CH- eclipsed "flagpole" interactions 2.5
CH3: iPr gauche 1.3
CH3: tBu gauche 2.1
CH3: H 1,3-diaxial 1.0
tBu: H 1,3-diaxial 2.0
iPr: H 1,3-diaxial 1.3
Staggered interactions 0

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Draw the C1-C2 Newman projection of the following molecule:

PRACTICE: Balance the following combustion reaction by providing the appropriate coefficients on
the lines provided:

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

SUMMARY: Test 2: Stereocenter Test

PRACTICE: Locate all chirality centers in the following compound

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Circle the chiral centers of the following molecule:

SUMMARY: R and S Configuration

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Draw the structure of the following molecules. Make sure your strucuture show s the
stereochemistry of the alkene.

(S)–2,2–dibromo–1,4–nonanediol

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: There are 6 stereoisomers that have the name 2,5-dichloro-3-hexene. One of these
stereoisomers is drawn in the box labeled “A”. Please note that this structure is drawn in a manner
which shows the absolute stereochemistry clearly and unambiguously. In the box labeled “B”, draw
the enantiomer of A. In the box labeled “C”, draw the ACHIRAL diastereomer of A in which the
double bond has the (Z) configuration. In the box labeled “D”, draw the ACHIRAL diastereomer of
A in which the double bond has the (E) configuration. Remember, a molecule is ACHIRAL when it
IS superimposable on its mirror image! All of the structures that you draw should be line–angle
structures! In each structure, use wedges, dashed wedges, and normal lines (as appropriate) to
show the stereochemistry clearly and unambiguously.

* This review was not prepared by your professor or school and is neither approved nor endorsed by your college or university 29
TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Indicate the number of possible enantiomers for the following compound:

a) 0

b) 1

c) 2

d) 3

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Circle all the chiral structures given below.

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

SUMMARY: Meso Compound

PRACTICE: Which are meso compounds? For molecules which can readily change their
conformations, assume that any meso conformation(s) are accessible through bond rotations.

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

SUMMARY: What is the Relationship Between Isomers?

* This review was not prepared by your professor or school and is neither approved nor endorsed by your college or university 33
TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: How are the molecules shown below related to each other?

a. Identical

b. Constitutional Isomers

c. Enantiomers

d. meso compounds

e. diastereomers

* This review was not prepared by your professor or school and is neither approved nor endorsed by your college or university 34
TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Draw the Fisher projection of (2R,3S,5R)-5-bromohexa-2,3-diol.

Name and draw two diastereomers of the above compound.

Name and draw the enantiomer of the compound.

* This review was not prepared by your professor or school and is neither approved nor endorsed by your college or university 35
TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Circle the structure that represents (2S,3R)-2-bromo-2-chlorohex-4-yne-1,3-diol.

PRACTICE: Compound C has an [a] D = +28°.

a) Draw the structure of compund D, which is isomer of C and features an [a] D = -28°.

b) Calculate the [a] D of a 25/75 mixture of derivatives C and D, respectively.

c) Draw the structure of a compound E, which is an isomer of C and D, and features an [a] D = 0°

* This review was not prepared by your professor or school and is neither approved nor endorsed by your college or university 36
TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Classify the following reactions (1-4) as addition, elimination, substitution, or


rearrangement from top to bottom:

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Draw curved arrows to represent the flow of electrons in each step, and indicate the
missing fragments in the box

SUMMARY: Nucleophiles and Electrophiles

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Identify nucleophiles and electrophiles of the following reactions.

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

SUMMARY: Acids and Bases

PRACTICE: Circle the compounds below which can act as Lewis bases and put a box around the
compounds which can act as Lewis acids.

But first, select only Lewis Bases from the compounds below:

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

SUMMARY: Acid and Base Conjugates

PRACTICE: The following is a stepwise synthesis by applying Bronsted-Lowry (B-L) and Lewis
acid-base (LA and LB) reactions. Please use electron-pushing arrows to show this transformation
logically.

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Please answer the following two questions below.

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

SUMMARY: pKa

PRACTICE: Circle the most acidic proton in each of the following molecules.

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Which one of the following reactions will be favorable?

PRACTICE: The Markovnikov product, resulting from an addition reaction to an unsymmetrical


alkene, is formed because:

A. The product is statistically favored.

B. Steric hindrance favors its formation.

C. The reaction proceeds via the more/most stable carbocation.

D. The reaction forms the more/most stable product.

E. All of the above are valid reasons.

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

SUMMARY: Acid-Catalyzed Hydration

PRACTICE: Illustrate the mechanism for the following reaction. Indicate all arrows and structures of
intermediates.

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

SUMMARY: Oxymercuration

PRACTICE: Predict the product:

SUMMARY: Halohydrin

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Complete the following reaction and show the complete arrow-pushing mechanism
required to produce the product. Show stereochemistry.

SUMMARY: Ozonolysis

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Consider the structures below and answer the following questions.

e. Which compounds each form a single product on treatment with O3 / (CH3)2S?

SUMMARY: Oxidative Cleavage

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Predict the product of the following reaction. Show stereochemistry when applicable.

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Provide correct product(s) for the following reactions, demonstrating correct
stereochemistry in your products. If the product has an enantiomer or diastereomer, then just
write +E or +D as necessary. Finally, indicate if the reaction undergoes ANTI or SYN addition (if a
mechanism undergoes both then circle both words).

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Complete the following set of reactions by supplying the missing reagents

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Predict the product of the reaction:

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Which is the correct sequence of reaction steps necessary to complete the
following transformation?

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Predict the product for the reaction below.

SUMMARY: Hydrogenation of Alkynes

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Give all possible product/products and designate stereoselectivity &/or regioselectivity
by using wedges and dashes.

PRACTICE: Which reagents below would be used to convert 2-pentyne to trans-2-pentene?

A. NaNH2, NH3

B. (1) Na, EtNH2 (2) NH4Cl

C. H2, Lindlar's catalyst

D. H2 / Pt.

SUMMARY: Alkyne Hydrohalogenation

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Determine the major product for the alkyne reaction below.

SUMMARY: Alkyne Halogenation

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Careful addition of 1 equivalent of Br2 to the alkyne shown below would be expected to
produce which of the following as the major organic product?

SUMMARY: Alkyne Hydroboration

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Predict the product for the reaction below.

PRACTICE: Show how you would carry out each of the following reactions. You do NOT need to
draw the mechanisms

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

SUMMARY: Alkynide Synthesis

PRACTICE: Predict the product for the following reaction:

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

SUMMARY: Radical Stability

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Which of the following radicals is the most likely to form during the propagation phase
of a radical chain reaction?

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

SUMMARY: Free Radical Halogenation

PRACTICE: Propose a mechanism for the radical chlorination of methane. Include its initiation,
propagation, and termination steps.

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Approximate the heat of reaction for the given halogenation reaction.

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: The reaction coordinate diagram below is an example of the application of Hammond
postulate to carbocation formation in an SN1 reaction. Based on the reaction coordinate diagram
below, which of the following statements is FALSE?

A. The relative stabilities of the carbocation decreases in the following order: 3o > 2o > 1o

B. The transition state shifts towards the reactant with increasing carbocation stability.

C. The transition state become more stable as the reaction becomes less endothermic.

D. The most stable transition state resembles the product more than any other transition state.

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Upon treatment of 1-methylcyclopentene with NBS and irradiation with UV light,
exactly nine compounds (including stereoisomers) are formed. Draw any four of the possible
products.

SUMMARY: Anti Markovnikov Addition of Br

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Determine the mechanism and predict the product of the reaction:

PRACTICE: Propose a synthetic way to produce the following compound.

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Show how you would carry out each of the following reactions. You do NOT need to
draw the mechanisms

PRACTICE: Rank in order of leaving group ability (1 = best leaving group, 4 = worst leaving group).

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TEXAS CH 320M COLAPRET FINAL REVIEW*

SUMMARY: SN2 Reaction

PRACTICE: The derivative shown undergoes an SN2 substitution reaction with NaCN. Draw the
resulting organic product. Assign the R or S configuration to the starting reactant (starting
derivative) and the product. Briefly comment on the result.

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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*

SUMMARY: SN1 reaction

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PRACTICE: Draw the reaction mechanism and the energy diagram for the following
substitution reaction. Indicate if it follows an SN1 or an SN2 mechanism.

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TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: For the following reaction

a) Label the nucleophile, electrophile, and leaving group.

b) Identify if it follows SN1 or SN2 mechanism.

c) Provide a detailed curved arrow mechanism

PRACTICE: Which of the following shows a mechanism for an E2 elimination?

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TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Provide the major product for the following compound.

PRACTICE: Predict the major product(s). In the present case, the reaction needs to be
performed at 85°C. In fact, at 70°C the less stable chair conformation can be accessed.

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TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Draw the product of the E2 elimination of (1S,2R)-1,2-dibromo-1,2-diphenylethane


(shown below left). Draw the product in the box below provided and complete the
Newman projection of (1S,2R)-1,2-dibromo-1,2-diphenylethane looking along C1 to C2 in the
correct geometry required to yield the product.

SUMMARY: E1 Reaction

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TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Which of the following shows the first step for an E1 reaction?

PRACTICE: Which conditions favor an efficient nucleophilic substitution reaction on 1-


chlorobutane?

a. A weak nucleophile in a polar protic solvent

b. A weak nucleophile in a polar aprotic solvent

c. A strong nucleophile in a polar protic solvent

d. A strong nucleophile in a polar aprotic solvent

e. A strong nucleophile in a nonpolar solvent

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TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Rank the following in decreasing order of leaving group ability.

a) I > III > IV > II

b) I > III > II > IV

c) III > II > I > IV

d) II > I > III > IV

PRACTICE: Which is the strongest nucleophile?

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SUMMARY: SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)

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TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Predict the product(s) for the following reaction.

SUMMARY: Zaitsev Rule

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TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Provide the major product for the following compound.

PRACTICE: The following reaction below is probably

A) an SN1-type reaction involving the protonated alcohol as the substrate.

B) an SN2 -type reaction involving the protonated alcohol as the substrate.

C) an E1 -type reaction involving the protonated alcohol as the substrate.

D) an E2 -type reaction involving the protonated alcohol as the substrate.

E) an epoxidation reaction.

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TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Predict the product of the following reaction, showing stereochemistry if applicable. If
there is no reaction, just write “no reaction” in the box.

SUMMARY: Dehydration Reaction

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TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: 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.

SUMMARY: Oxidizing Agent

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TEXAS CH 320M COLAPRET FINAL REVIEW*

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

SUMMARY: Naming Ethers

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TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Provide the IUPAC name of the following ether.

SUMMARY: Williamson Ether Synthesis

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TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Which compound will be the organic product after the following two steps?

SUMMARY: Making Ethers - Acid-Catalyzed Alkoxylation

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TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Predict the following synthesis:

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TEXAS CH 320M COLAPRET FINAL REVIEW*

SUMMARY: Williamson Ether Retrosynthesis

PRACTICE: Show what reagents you would use to prepare the ether via the Williamson
Ether Synthesis.

SUMMARY: Epoxidation

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TEXAS CH 320M COLAPRET FINAL REVIEW*

PRACTICE: Predict the product of the following reaction:

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TEXAS CH 320M COLAPRET FINAL REVIEW*

SUMMARY: Sharpless Epoxidation

PRACTICE: Predict the product of the following reaction showing stereochemistry if applicable.

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