Texas CH 320m Colapret Final Review

TEXAS - ORGANIC CHEMISTRY I - PROF.
COLAPRET
TEXAS CH 320M COLAPRET FINAL REVIEW*
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TEXAS - ORGANIC CHEMISTRY I - PROF. COLAPRET
PRACTICE: Which one of the following best represents the shape of δ* anti-bonding molecular
orbital?
SUMMARY: Formal Charges
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
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
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.
SUMMARY: Resonance Structures
PRACTICE: Draw three other important resonance contributors for the molecule below.
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
PRACTICE: Indicate the hybridization for carbon a,b,c and d.
a. ____________ b. _____________
c. ____________ d. _____________
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
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.
SUMMARY: Functional Groups
PRACTICE: Identify ALL of the functional groups in the following molecule. Assign degree of
functional group when appropriate.
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
SUMMARY: Alkyl Groups
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
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?
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
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
PRACTICE: Which one of the following compound(s) is constitutional isomers of spiro[2.2]pentane?
SUMMARY: Intermolecular Forces
PRACTICE: Which of these compounds would have the highest boiling point?
a. I
b. II
c. III
d. IV
PRACTICE: Select the molecule with greater solubility in water. Provide a brief explanation.
Propanoic acid or Decanoic acid
SUMMARY: Drawing Newman Projections
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
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?
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.
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
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:
SUMMARY: Test 2: Stereocenter Test
PRACTICE: Locate all chirality centers in the following compound
PRACTICE: Circle the chiral centers of the following molecule:
SUMMARY: R and S Configuration
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
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.
PRACTICE: Indicate the number of possible enantiomers for the following compound:
a) 0
b) 1
c) 2
d) 3
PRACTICE: Circle all the chiral structures given below.
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.
SUMMARY: What is the Relationship Between Isomers?
PRACTICE: How are the molecules shown below related to each other?
a. Identical
b. Constitutional Isomers
c. Enantiomers
d. meso compounds
e. diastereomers
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.
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°
PRACTICE: Classify the following reactions (1-4) as addition, elimination, substitution, or

rearrangement from top to bottom:
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
PRACTICE: Identify nucleophiles and electrophiles of the following reactions.
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:
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.
PRACTICE: Please answer the following two questions below.
SUMMARY: pKa
PRACTICE: Circle the most acidic proton in each of the following molecules.
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.
SUMMARY: Acid-Catalyzed Hydration
PRACTICE: Illustrate the mechanism for the following reaction. Indicate all arrows and structures of
intermediates.
SUMMARY: Oxymercuration
PRACTICE: Predict the product:
SUMMARY: Halohydrin
PRACTICE: Complete the following reaction and show the complete arrow-pushing mechanism
required to produce the product. Show stereochemistry.
SUMMARY: Ozonolysis
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
PRACTICE: Predict the product of the following reaction. Show stereochemistry when applicable.
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).
PRACTICE: Complete the following set of reactions by supplying the missing reagents
PRACTICE: Predict the product of the reaction:
PRACTICE: Which is the correct sequence of reaction steps necessary to complete the
following transformation?
PRACTICE: Predict the product for the reaction below.
SUMMARY: Hydrogenation of Alkynes
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
PRACTICE: Determine the major product for the alkyne reaction below.
SUMMARY: Alkyne Halogenation
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
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
SUMMARY: Alkynide Synthesis
PRACTICE: Predict the product for the following reaction:
SUMMARY: Radical Stability
PRACTICE: Which of the following radicals is the most likely to form during the propagation phase
of a radical chain reaction?
SUMMARY: Free Radical Halogenation
PRACTICE: Propose a mechanism for the radical chlorination of methane. Include its initiation,
propagation, and termination steps.
PRACTICE: Approximate the heat of reaction for the given halogenation reaction.
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.
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
PRACTICE: Determine the mechanism and predict the product of the reaction:
PRACTICE: Propose a synthetic way to produce the following compound.
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).
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.
SUMMARY: SN1 reaction
PRACTICE: Draw the reaction mechanism and the energy diagram for the following
substitution reaction. Indicate if it follows an SN1 or an SN2 mechanism.
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?
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.
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
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
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?
SUMMARY: SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)
PRACTICE: Predict the product(s) for the following reaction.
SUMMARY: Zaitsev Rule
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.
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
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
PRACTICE: What is the major product of the following rxn:
SUMMARY: Naming Ethers
PRACTICE: Provide the IUPAC name of the following ether.
SUMMARY: Williamson Ether Synthesis
PRACTICE: Which compound will be the organic product after the following two steps?
SUMMARY: Making Ethers - Acid-Catalyzed Alkoxylation
PRACTICE: Predict the following synthesis:
SUMMARY: Williamson Ether Retrosynthesis
PRACTICE: Show what reagents you would use to prepare the ether via the Williamson
Ether Synthesis.
SUMMARY: Epoxidation
PRACTICE: Predict the product of the following reaction:
SUMMARY: Sharpless Epoxidation
PRACTICE: Predict the product of the following reaction showing stereochemistry if applicable.

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Texas CH 320m Colapret Final Review

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TEXAS - ORGANIC CHEMISTRY I - PROF.

SUMMARY: Formal Charges

E. More than one of these

SUMMARY: Resonance Structures

e. All have the same geometry

f. none of the above

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

secondary carbocation dialkyloxonium ion

2° amine phenyloxonium ion

pKa benzyl halide

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

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.

SUMMARY: Functional Groups

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

SUMMARY: Alkyl Groups

E. None of the above

E. None of the above

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

SUMMARY: Degrees of Unsaturation

SUMMARY: Constitutional Isomers

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

SUMMARY: Intermolecular Forces

Propanoic acid or Decanoic acid

SUMMARY: Drawing Newman Projections

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

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

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?

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?

What is the name of this form? _______________

Interaction Energy Table:

Interaction Energy (kcal/mol)

H:H eclipsed 1.0

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

SUMMARY: Test 2: Stereocenter Test

PRACTICE: Locate all chirality centers in the following compound

PRACTICE: Circle the chiral centers of the following molecule:

SUMMARY: R and S Configuration

PRACTICE: Circle all the chiral structures given below.

SUMMARY: Meso Compound

SUMMARY: What is the Relationship Between Isomers?

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.

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°.

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

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

SUMMARY: Nucleophiles and Electrophiles

PRACTICE: Identify nucleophiles and electrophiles of the following reactions.