Chemistry 201
Clark College
Exam 3 Review Sheet
The standard disclaimer applies!
1. Predict the products for the following reactions. If more that one product can be formed, give all
products. Categorize reactions as SN1, SN2, E1 or E2, where applicable.
O
O
H
OH
1) NaBH4
2) H3O+
OH
O
OH
SOCl2
OH
OH
SN2
Cl
OH
HCl
1) Na0
2) CH3CH2Br
Because Cl- is a particularly lousy based,
you would only get the SN1 product.
Cl
O
SN2 - the sodium metal pulls the H off of the alcohol,
making it a strong anionic nucleophile.
E2
LDA
Br
Cl
SN2, not the inversion of stereochemistry
NaOH
OH
OH OH
CrO3, H3O+
OH O
a tertiary alcohol cannot be oxidized!
O
OH
1) LiAlH4
OH
2) H2O
Cl
CH3OH
O
SN1 and E1
NaOCH3
OH
Exam 3 Review Sheet
O
SN1 and E1
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Chemistry 201
Clark College
2. Road Map. Give the identities for compounds A – D, based on the following synthetic sequence.
If you get stuck, but know what the reaction does, please indicate this for partial credit.
Cl
Compound A:
Cl
Compound B:
MgCl
Compound C:
Compound D:
3. Which of the following two phenols is more acidic? Use resonance structures to determine which
compound forms the more stable anion.
OH
O
O
O
O
O
-H+
O
O
O
O
O
O
O
The para substituted phenol contributes another resonance
to the anion/conjugate base. The extra resonance structure
results in a more stable anion, and a more acidic proton.
O
OH
O
O
O
O
O
-H+
O
Exam 3 Review Sheet
O
O
O
O
O
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Chemistry 201
Clark College
4. Arrange the following molecules in order of increasing acidity (decreasing pKa):
Cyclohexanol, phenol, p-nitrophenol, 2-chlorohexanol.
OH
OH
OH
OH
Cl
>
>
>
NO2
5. Nomenclature. Name the following compounds.
3-ethoxy-4-fluorotoluene
O
Cyclohexyl isopropyl ether
O
F
OH
(1R, 2R)-2-methyl-1-cyclobutanol
E-but-2-en-1-ol
OH
Yes, this is a cyclobutane!
6. Determine the compound described by the spectra below:
C5H11Br
Br
The structural formula gives 0 units of unsaturation, and fewer peaks often means a fairly symmetric
molecule.
Exam 3 Review Sheet
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Chemistry 201
Clark College
7. Synthesis. Synthesize the following molecules from the given starting materials and any other
reagent needed.
a) Ethyl t-butyl ether from 1-bromo-1,1-dimethylethane
LDA
CH3CH2OH
Br
OCH2CH3
H+
SH
b)
from
1) BH3
2) NaOH, H2O2
OH
SOCl2
Cl
c) 2-bromobutane from butanol
OH
LDA
from
HBr
NaSH
SH
Br
Br
d)
Br
Exam 3 Review Sheet
Mg0
ether
BrMg
Br
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Chemistry 201
Clark College
8. Give the reagents needed to perform the following transformations along a synthetic pathway.
CH3
CH3
CH3
CH3
O
O
O
O
1) Mg,
ether
Br2
(CH3)3CCl
FeBr3
2) H2O
AlCl3
Br
Br
9. Treatment of 1-buten-3-ol with concentrated HCl yields two products, 3-chloro-1-butene and 1chloro-2-butene. Write a mechanism that explains how both products are formed. HINT: try
drawing resonance structures of your intermediate.
OH
H Cl
OH2
+ ClCl
Exam 3 Review Sheet
+ ClCl
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