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Organic Chemistry Jeopardy
Products
Conditions
Nuc / base
mechanism
Reactants
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©Norman Herr, 2000
A-100
• ANSWER: The products of this reaction
CH3CH2CH2Br + CH3O-1 in CH3OH at 50o
• QUESTION: SN2 gives methoxypropane
E2 gives propene
What is methoxypropane?
Answer
Question
A-200
• ANSWER: The products of this reaction
CH3CH2CH2Br + (CH3)3CO-1, 50o,
(CH3)3COH 
• QUESTION: SN2 gives t-butoxypropane
E2 gives propene
What is propene?
Answer
Question
A-300
• ANSWER: The products of this reaction
CH3CH2CHBrCH3 + HS-1, 50o, CH3OH
• QUESTION: SN2 gives 2-butanethiol
secondary RX, good Nu, weak base
What is 2-butanethiol?
Answer
Question
A-400
• ANSWER: The products of this reaction
(CH3CH2)3CBr + OH-1, 50o, CH3OH 
• QUESTION: E2 reaction
What is 3-ethyl-2-pentene?
Answer
Question
A-500
• ANSWER: The products of this reaction
(CH3CH2)3CBr + CH3OH, 25o 
• QUESTION: E1 gives minor product:
3-ethyl-2-pentene
What is 3-ethyl-3-methoxypentane?(SN1)
Answer
Question
B-100
• ANSWER: These reactions are increased
by high temperatures
• QUESTION:What are elimination
reactions?
Answer
Question
B-200
• ANSWER: A reaction promoted by a
poor nucleophile in a protic solvent.
• QUESTION: What is an SN1 reaction?
Answer
Question
B-300
• ANSWER: Ethanol is this type of
solvent.
• QUESTION: What is a polar protic
solvent?
Answer
Question
B-400
• ANSWER: Reaction(s) that never
occur(s) in a strongly basic solution.
• QUESTION: What are SN1 and E1
reactions?
Answer
Question
B-500
• ANSWER: Reaction(s) that do(es) not
require a polar solvent.
• QUESTION: What is an E2 reaction?
Answer
Question
C-100
• ANSWER: Reaction(s) that require(s) a
strong base.
• QUESTION: What is an E2 reaction?
Answer
Question
C-200
• ANSWER: Reaction(s) that don’t
require strong bases or strong
nucleophiles.
• QUESTION: What are SN1 and E1
reactions?
Answer
Question
C-300
• ANSWER: LDA always gives this
reaction.
• QUESTION: What is an E2 reaction?
Answer
Question
C-400
• ANSWER: A secondary alkylbromide
reacts with methylamine through this
mechanism.
• QUESTION: What is an SN2
mechanism?
Answer
Question
C-500
• ANSWER: Lithium diisopropyl amide
(LDA) reacts through only E2 reactions
while lithium amide uses these.
• QUESTION: What are E2 and SN2
reactions? Sterics affect the reaction
mechanism used!
Answer
Question
D-100
• ANSWER: Reaction(s) that have a
carbocation as an important
intermediate.
• QUESTION: What are SN1 and E1
reactions?
Answer
Question
D-200
• ANSWER: Reaction(s) that are second
order.
• QUESTION: What are SN2 and E2
reactions?
Answer
Question
D-300
• ANSWER: Reaction(s) that occur in one
step.
• QUESTION: What are SN2 and E2
reactions?
Answer
Question
D-400
• ANSWER: Reaction(s) that react in a
specific orientation.
• QUESTION: What are SN2 and E2
reactions? SN2 inversion occurs from
the backside and in E2 the antiperiplanar
hydrogen is removed.
Answer
Question
D-500
• ANSWER: The isomer of 3-t-butyl-1chlorocyclohexane which reacts faster
• QUESTION: What is the trans isomer?
Answer
Question
E-100
• ANSWER: The solvent itself acts as a
nucleophile in this type of reaction.
• QUESTION: What is solvolysis?
Answer
Question
E-200
• ANSWER: Mechanism(s) tertiary
alkylhalides will proceed through.
• QUESTION: What are SN1, E1, E2
reactions? (so do secondary alkylhalides)
Answer
Question
E-300
• ANSWER: This is used to give the less
substituted product in an E2 elimination
reaction with a secondary alkylhalide.
• QUESTION: What is a sterically
hindered strong base used for? (tbutoxide, LDA)
Answer
Question
E-400
• ANSWER: Methods to make alcohols
into a good leaving groups and retain
their stereochemistry.
• QUESTION: What are protonation,
tosylation, and triflation?
(Add acid, Tosylchloride, or trifyl
chloride)
Answer
Question
E-500
• ANSWER: A method to make 100% (R)2-cyanobutane from (R)-2-chlorobutane.
• QUESTION: What is the reaction of (R)2-chlorobutane with sodium iodide in
acetone, followed by sodium cyanide in
acetone?
Answer
Question