Problems 2 Summer 2024
(These problems focus on Alkene Reactions; Chapters 4, 5, 11 and 12)
1. Give the products of the following reactions. You should include the mechanism for each
reaction. Indicate stereochemistry where appropriate. Pay attention to rearrangements where
applicable. Being able to write the product without understanding the mechanism is of no value.
CH3 CH3OH
a)
H2SO4 (catalyst)
H t-Bu
b) HBr
C C
H H
c) CH3 CH3 H2
Pd
H
d) 1. BH3
2. H2O2/NaOH
H2O
Ph CH CH CH2
e) H2SO4 (catalyst)
CH3
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CH2
KMnO4
f)
heat
2. Show the products of the following reaction sequence. Show all carbon-carbon bonds clearly.
H 3C CH3
C C + BH3 A
H3C H 1 mole
1 mole Note: There is no H2O2 or NaOH
added to these reactions
H 3C CH3
A + C C B
H 3C H
What product is formed when B reacts with H2O2 and NaOH?
3. Give the reagents that could be used to carry out the following transformations. Clearly
indicate if more than one step is necessary. Write mechanisms for b-d.
C
H
a)
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OH
b)
OH
c)
H
O
d) CH3
4. What is the product of the reaction of HCCl3 with KO-t-Bu (or KOH) in the presence of
cyclohexene?
K+ t-BuO-
+ HCCl3
or KOH
Write a complete mechanism using arrow formalism for the reaction of HCCl3 with KO-t-Bu.
Show a 3-dimensional structure of the reactive intermediate involved in this reaction.
5. Iodine azide (IN3) reacts with the alkene shown below to give the product with the
stereochemistry shown.
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N3 CH3
CH3 CH3 H
IN3
CH3
Et H I
Et
Show a Lewis structure for IN3 with all non-bonding electrons and formal charges.
Give a detailed mechanism for the reaction. Your mechanism must account for the
stereochemistry and the regiochemistry of the reaction.
6. Predict the product of the following reaction. You must write a mechanism.
O
CH3OH
H2SO4 (catalyst)
Explain why this reaction is so much faster than that of cyclohexene under the same conditions?
A precise explanation using precise structures and about 10 words are required. If you feel the
need to write an essay, then you probably do not understand the principle involved.
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7. Draw Lewis structures of each and circle the electrophile(s).
CH3 CH3
B
CCl2 P(CH3)3
8. Ozonolysis of a compound of formula C10H16, followed by reduction with Zn, gives only the
following 2 products. What is the structure of this hydrocarbon C10H16?
O O O O
1. O 3
C10H16 H C C H + CH3 C CH2 CH2 C CH CH3
2. Zn
CH3
9. Circle the indicated compound or process.
a) The most exothermic reaction. Explain why you circled this reaction.
Me H
C Me + Cl C Me + Cl
Me Me
H
+ Cl
C Me + Cl
H
b) The carbocation which does not rapidly rearrange. Write the rearranged cations for
the ones that you didn't circle.
CH3 CH3 CH2 CH3
CH3
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c) The least stable alkene (releases the most heat when hydrogenated). Explain why.
CH3
10. The carbocation shown below rearranges readily to a more stable cation. Show the structure
of this rearranged carbocation. Use arrow formalism to explain the rearrangement.
11. Show structures of the following.
(a) The adducts formed when ozone reacts with 2-methylpropene (isobutylene). A 3-D
structure is not necessary.
(b) The product formed when one mole of BH3 reacts with 3 moles of propene. Show all atoms
in the product. Show the product before addition of H2 O2/NaOH. A 3-D structure is not
necessary.
(c) The resonance forms of the intermediate formed when the enol below is protonated in acid.
What is the final product (a stable molecule) of this transformation?
H OH
H+
C C
H H
12. Propose a detailed mechanism (showing all intermediates) for the following reaction.
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O
Br2
CH3 C C H CH3 C CH2Br
H2O (solvent)
13. Write a mechanism for the following reaction. Draw an Energy vs. Progress of Reaction
Diagram for this reaction. Be certain that the intermediates are clearly indicated on this diagram.
H 3C Cl
HCl
Progress of Reaction
14. Write a mechanism for the following reactions.
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O O
HO H 2O
O
H2SO4 (cat)
1. Hg(OAc)2 in H2O (2 moles)
O
2. NaBH4
15. Give the products of the following reactions.
H
1. OsO4
H 2. NaHSO3 in H2O
CH2
Cl
H
+
18
O O
18
O
CH3
1. Hg(OAc)2 in CH3OD
2. NaBH4
16. Provide reagents that could be used to carry out the following transformation. Write a
mechanism for this reaction.
OCH3
Cl
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