1.
Structure and Bonding
1.1 Which of the following molecules have a dipole moment?
a) Cyclohexane
b) Trichloromethane
c) Tetrafluoromethane
d) Cyclohexanol
1.2 Is this molecule aromatic, anti-aromatic or non aromatic?
a) aromatic
b) anti-aromatic
c) non aromatic
1.4 The conjugate base of 4-Nitrophenol has more relevant resonance structures than
that of 3-Nitrophenol [T/F]
a) true
b) false
2. Functional Groups, Conformation
2.1 Choose the more energetically favorable conformation for
cis-1-ethyl-2-methylcyclohexane:
a. Both ethyl and methyl groups in axial positions
b. Ethyl in axial, methyl in equatorial
c. Ethyl in equatorial, methyl in axial
d. Both ethyl and methyl groups in equatorial positions
2.2 Indicate the absolute configuration of stereogenic centers in the following
molecules:
a. R
b. S
c. No stereogenic center
2.3 Identify the relationship between the following pair of compounds:
threo-2,3-dibromobutane and meso-2,3-Dibromobutane
a. Constitutional isomers
b. Diastereomers
c. Enantiomers
d. No isomeric relationship
3. Chirality, Mass Spectrometry, Spectroscopy
3.1 Based on the spectra below which is the corresponding compound?
A. Compound A
B. Compound B
C. Compound C
D. Compound D
3.2 All-trans retinol and all-trans retinal are molecules play important roles in
vision as part of rhodopsin.
3.2.1. Given the structures which structure absorbs at a longer UV-Vis
wavelength?
A. Retinol
B. Retinal
3.2.2 Does the IR-spectra below correspond to retinal or retinol?
A. Retinol
B. Retinal
4. NMR, Structure determination
4.1 To which molecule does the following 1H-NMR spectrum belong?
4.2 The provided 1H-NMR spectrum corresponding to the molecule below is
missing a peak. How can this missing peak be characterized?
A) 1, s
B) 1, q
C) 2, s
D) 2, q
4.3 The 1H-NMR spectrum corresponds to the shown molecule. Which
hydrogen is represented by the peak indicated with the red arrow?
E) Hydrogen A
F) Hydrogen B
G) Hydrogen C
H) Hydrogen D
5. Organic reactivity / Acid Base
5.1 Use the reaction coordinate diagram below to indicate if the following
statements below are true or false.
I. Keq of this reaction is > 1
a)True
b)False
II. This reaction has 2 steps
a)True
b)False
III. Step A - B is the rate determining step of the forward reaction
a)True
b)False
5.2 Which sentences about the equation below are true (Multiple answers possible)
HF + H2O → H3O+ + F-
A. H2O is a base and HF is its conjugate acid.
B. H2O is an acid and HF is the conjugate base.
C. HF is an acid and F- is its conjugate base.
D. HF is a base and H3O+ is its conjugate acid.
E. HF is a base and F- is its conjugate acid
5.3 Rank following molecules in order of increasing acidity (One possible answer)
A. Molecule A > Molecule C > Molecule B
B. Molecule A > Molecule B > Molecule C
C. Molecule B > Molecule C > Molecule A
D. Molecule B > Molecule A > Molecule C
E. Molecule C > Molecule A > Molecule B
F. Molecule C > Molecule B > Molecule A
6. Nucleophilic Substitutions
6.1 Chose the correct answer
6.2 Order the four carbon centers 1 to 4 shown below by decreasing likelihood of
undergoing an SN1 reaction.
A. 1, 4, 3, 2
B. 1, 4, 2, 3
C. 3, 1, 4, 2
D. 4, 1, 3, 2
6.3 Rank the carbocations 1 to 4 from least to most stable
A. 3, 2, 1, 4
B. 3, 1, 2, 4
C. 2, 3, 4, 1
D. 4, 3, 2, 1
7. Phosphate transfer reactions
7.1 Which of the following compound shows the correct decreasing order of
solvolysis with aqueous ethanol?
The correct choice is:
a) III > II > I > IV
b) III > II > IV > I
c) II > III > IV > I
d) III > I > IV > II
7.2 What type of reaction takes place upon treatment of a ketone with HCN to form
a cyanohydrin?
a) Nucleophilic addition
b) Nucleophilic substitution
c) Electrophilic addition
d) Electrophilic substitution
7.3 Which of the following curves correctly represents SN1 vs SN2?
a) b)
c) d)
8. Addition reactions
8.1. Which of the proposed products can form in the given reaction?
a) b) c) d)
No reaction
8.2. RNA is significantly less stable than DNA. In basic solutions RNA strands can be
hydrolyzed, which of the following products could be created under basic conditions?
a) b)
c) d)
no reaction
8.3. Carbonyl Addition
Which of the proposed products can form in the given reaction?
a) b) c) d)
no reaction
9. Nucleophilic Additions to Carbonyl Compounds
9.1. Which response contains the correct names for the functional groups in A-E
1: A=Hemiketal, B=Acetal, C=Hemiacetal, D=Ketal, E=Hydrate of an Aldehyde
2: A=Hemiacetal, B=Acetal, C=Hemiketal, D=Ketal, E=Hydrate of a Ketone
3: A=Hemiketal, B=Acetal, C=Hemiacetal, D=Ketal, E=Orthoester
4: A=Hemiketal, B=Acetal, C=Hemiacetal, D=Acetal, E=Hydrate of an Aldehyde
9.2 Does this reaction take place? (T/F)
9.3 Does this reaction take place? (T/F)
10. Reactions in alpha carbons
10.1 Which of these are true and which are false about enols and enolates?(T/F)
• Enols are the highly reactive resonance forms of ketones and aldehydes.
• The carbon adjacent to the carbonyl group (C=O) is unusually acidic and is known
as the "alpha carbon."
• The enolates of amides and esters are easiest to form, followed by ketones and
aldehydes.
• In basic conditions, aldehydes and ketones can be deprotonated at the alpha
position to form enolate ions.
• Enolates are ambident nucleophiles, meaning they can react at both the oxygen and
carbon atoms.
• In the presence of acid, ketones and aldehydes can be converted into enols through
a process called tautomerization.
• The stability of the enol form increases when it can be conjugated with an adjacent
pi-system
• Enolates can be formed from aldehydes and ketones by using weak bases such as
carbonate or acetate
• Enolates are useful intermediates in carbon-carbon bond-forming reactions such as
the Aldol reaction and Claisen condensation.
10.2. The following reaction is an example of:
A) SN2 Substitution
B) Aldol Reaction
C) Nucleophilic Acyl Substitution
D) Electrophilic Addition
E) Claisen Condensation
11. Electrophilic reactions
11.1. Aldol addition
Which of the given starting materials can lead to the following Aldol addition ?
a) b)
c) d)
11.2. Aldol addition
The following ester is treated with a strong base, followed by the addition of the
aldehyde and a final aqueous work-up. Which of the products would you expect?
a) b)
c) d)
11.3. Decarboxylation
the following natural product can undergo heat activated decarboxylation? Hint: there
is an enol in this molecule.
a) True
b) False
12. Redox reactions
12.1 Which would be suitable reagents for the following transformations?
a) CrO3
b) HCl
c) NaBH4
d) NaOH
12.1 Which would be suitable reagents for the following transformations?
a) CrO3
b) HCl
c) NaBH4
d) NaOH
12.2 The structure below corresponds to the oxidized form of the NAD(P)+ /
NAD(P)H, H+ pair.
a) True
b) False
