Alkene Reactions
(Vollhardt & Schore, Chapter 12; a student designed Jeopardy! game)
Single Jeopardy Answers
1. Stereochemistry and Regiochemistry
Pts Answer
50
Type of addition that is found in catalytic
hydrogenation of alkenes.
100 Type of addition found in bromohydrin
formation.
150 Two characteristics of hydroboration-oxidation.
200
250
Question
What is syn addition?
What is anti addition?
What are syn addition and antiMarkovnikov products?
What is meso-2,3-dibromobutane?
What is racemic –2,3-butanediol?
The bromination of cis-2-butene forms ____.
1. MCPBA, CH2Cl2
H
H
2. H3O+
?
H3C
106765448
CH3
1
3/9/16
Alkene Reactions
(Vollhardt & Schore, Chapter 12; a student designed Jeopardy! game)
2. Grab Bag
50
Pd/C or PtO2
100
A 2 step method to convert an alkene to an
alkane.
150
3 methods of obtaining alcohols from alkenes.
200
Solution that when red color is removed indicates
the added compound was an alkene.
The order or rate of oxacyclopropane formation
of the following, from slowest to fastest:
RCH=CHR, R2C=CR2, R2C=CH2, CH2=CH2.
250
3. Reactions Types
50
Adds H and OH via syn addition via a
carbocation intermediate.
100 Used to hydrate alkenes without involving a
carbocation.
150 A process by which 2 dimers further react to form
a longer chain.
200 Type of polymerization initiated by strong bases.
250 Used to make 1o alcohols when the substrate
alkene could form 2o or 3o alcohols.
2
What are catalysts in catalytic
hydrogenation?
What is hydroghalogenation
followed by a Grignard reagent
quenched by water?
What are acid-catalyzed hydration,
hydroboration-oxidation, and
oxymercuration-demercuration?
What is bromine-water?
What is CH2=CH2, < RCH=RCH <
R2C=CH2 < R2C=CR2?
What is hydration?
What is oxymercurationdemercuration?
What is oligiomerization?
What is anionic polymerization.
What is hydration via
hydroboration-oxidation?
Alkene Reactions
(Vollhardt & Schore, Chapter 12; a student designed Jeopardy! game)
4. Reactions
50
H2
Pd/C
?
What is propene?
H H
H C C H
H H
100
MCPBA
?
What is
CH2Cl2
?
O
150
200
250
1. BH3, THF
2. H2O2, NaOH
?
What is OH
What are homolytic cleavage of the
peroxide to two alkoxy radicals and
hydrogen atom abstraction from
HBr by the alkoxy radical?
The two initiation steps of peroxide-catalyzed
radical hydrobromination.
KMnO4
HOH2O
?
What is
3
OH
OH
Alkene Reactions
(Vollhardt & Schore, Chapter 12; a student designed Jeopardy! game)
5. Carbocations
Pts Answer
50
Hybridization of the C in most carbocations.
100
HCl
Question
What is sp2?
What is racemic-2-chlorobutane?
?
CCl4
HCl
150
?
CCl4
200
250
What is 2-chloro-2,3dimethylbutane?
The carbocation generated from alkenes is
derived from a loss of these.
Chain lengthening step in cationic
polymerization.
6. Products
Pts Answer
50
O
HBr
150
What is attack of the alkene on a
carbocation?
Question
What is 2-bromoethane?
?
CH2CH3
100
What are pi bonding electrons?
Br2
HCl
What is 1-chloro-1propylcyclohexane?
?
What is racemic 1,2dibromocyclohexane?
?
CCl4
1. BH3, THF
2. H2O2, NaOH, H2O
200
250
What is 2-methylpropanol?
?
CH2
1. OsO4, CH2Cl2
2. Zn, HOAc
4
What is cyclopentanone plus
formaldehyde?
?