Exam 3 Practice Exam
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Exam 3 Practice Exam Learning Objectives and Terms for Exam 3: Chapter 6/7: •
Discuss and utilize characteristics that effect nucleophilic substitution and elimination: Leaving groups, nucleophilicity/basicity, and solvent type
•
Differentiate between and draw Sn1/Sn2/E1/E2 mechanisms
•
Discuss the characteristics of S Sn1/Sn2/E1/E2 reactions with weak bases and alcohols
•
Draw appropriate energy diagrams for the mechanism type
•
Determine the Products when given the substrate and nucleophile/base
•
Give nomenclature or draw structure from IUPAC for alkenes
•
Know how to prepare alkenes with 1: alcohols and 2: alkyl halides and draw the mechanisms with energy coordinate diagrams
•
Discuss and apply the Zaitsev’s Rule/Hoffmann
•
Differentiate between when a substitution creates a major product and a elimination reaction creates a major product
•
Determine the appropriate product and/or reagents
•
Determine the reagent when given a substrate and product and retrosynthetic analysis
Definitions: Heat of reaction, Exothermic/endothermic , Spontaneous, Rate equation/rate order, Catalyst, Transition state/intermediate, Nucleophile/electrophile/carbocation, Nucleophilic attack/loss of leaving
group/ proton transfer/ rearrangement, Substitution reaction, Substrate/leaving group, Primary,secondary,tertiary alkyl halides, Concerted vs stepwise process, SN1 vs SN2, Rate determining step, Solvents: protic/aprotic, Sovolysis, Alkene, Beta elimination, Dehydrohalogenation, Regiochemistry, Zaitsev product/Hofmann product, Anti/syn, E1 vs E2
I: Multiple Choice: Choose the most correct
answer for the following questions. Some questions may have one answer and some may have multiple. 1.
What is the electrophile in the following reaction?
a.
I
b.
II
c.
III
d.
IV
2.
Answer the next few questions about the provided energy coordinate diagram. How many intermediates are included in the energy diagram? a.
1
b.
2
c.
3
d.
4
e.
5
True or False: The following energy diagram, is an endothermic reaction?
a.
TRUE
b. FALSE
3.
Select all the statements that are true for the following reaction.
a.
This is an Sn2 reaction
b.
This is an Sn1 reaction
c.
The rate of reaction would be: Rate = k [sub]
d.
The rate of reaction would be: Rate = k [sub] [nuc]
e.
If the concentration of 1-chloro-3-methylbutane is doubled the rate would double. f. If the concentration of 1-chloro-3-methylbutane is doubled the rate would quadruple.
g.
If the concentration of 1-chloro-3-methylbutane is doubled and the sodium azide is doubled the rate would double.
4.
Answer the following questions about the provided reaction. The operating mechanism for the above reaction is: a.
Sn1
b.
Sn2
Select the transition state(s) for the above reaction. a.
I
b.
II
c.
III
d.
IV
In the above reaction the equilibrium will favor the: a.
Products
b.
Reactants
In the functional group in the organic product is:
a.
Alcohol
b. Thiol
c. Sulfide
d. Chloride
e. Halogen
f. Sodium
5.
Answer the questions about the following substrates.
Select the substrate(s) that could do a Sn2 reaction. a.
I
b.
II
c.
III
d.
IV
Select the substrate(s) that could do a Sn1 reaction. a.
I
b.
II
c.
III
d.
IV
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6.
Answer the questions about the following reaction. The operating mechanism(s) for the above reaction is/are: a.
Sn1
b.
Sn2
c.
E1
d.
E2
Select the major substitution product(s).
a.
I b.
II
c.
III
d.
IV
e.
V
Select the major elimination product(s).
a.
1,3-dimethylcyclohex-1-ene
b.
1,5-dimethylcyclohex-1-ene
c.
1,3-dimethylchloclohex-5-ene
d.
1,4-dimethylcyclohex-1-ene
e.
1,4-dimethylcyclohex-3-ene
7.
Which of the following mechanistic steps represents a correct nucleophilic attack?
8.
Which of the following is the correct mechanism for the elimination reaction of 2-bromo-2,3-
dimethylbutane with methoxide?
9.
Select the reagents needed to complete the following transformation. a.
HOCH
2
CH
3
b.
NaOCH
2
CH
3
, acetone
c.
NaOH, H
2
O
d.
NaBr, acetone
e.
NaOCH
3
, DMSO
f.
NaOCH
3
, HOCH
3
10.Select the reagents needed to complete the following two step transformation. 2-methylpentane
2-methylpent-1-ene
Step 1: a.
NaBr, acetone
b.
Br
2
, hv
c.
NBS, hv
Step 2: a.
NaOH, acetone
b.
tBuOK, tBuOH
c.
NaNH
2
, NH
3
d.
H
2
O
e.
HOCH
3
f.
NaH, acetone
II: Short Answer Questions: a.
Indicate if reaction 1 and 2 would undergo an SN1 or SN2 mechanism in the provided blank.
b.
Using complete sentences, describe if reaction 1 or reaction 2 is faster.
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III: Determine the Product: Substitution vs Elimination
For the following reactions: a.
Draw the product(s). b.
Label the product(s) as major or minor above the product. c.
Label the operating mechanism: Sn1, Sn2, E1, E2 above the product.
d.
Consider both regiochemistry and stereochemistry where applicable. (R or S, *R/S, E or Z)
IV: Determine the Product: Alcohol Reactions
For the following reactions: a.
Draw the product(s). b.
Label the product(s) as major or minor above the product. c.
Label the operating mechanism: Sn1, Sn2, E1, E2 above the product.
d.
Consider both regiochemistry and stereochemistry where applicable. (R or S, *R/S, E or Z)
V: Mechanisms: Substitution a) Give a curved arrow pushing mechanism for the following reaction. Show all electrons and formal charges. b) Label the provided organic product as SN1, SN2
c) Draw and energy coordinate diagram to represent the reaction.
VI: Mechanisms: Elimination
a) Give a curved arrow pushing mechanism for the following reaction. Show all electrons and formal charges. b) Label the provided organic product as E1, E2
VII: Synthesis: In the following transformations, determine the best reagents to give the final product(s). Provide the reagents, solvents, temperature considerations, and intermediates formed after each step.
+ a substitution product
+ sn1 product
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On a scale of 1 to 5, rate your confidence in this exam. 1 being the least confident and 5 being the most confident. 1
2
3
4
5
Evaluate your own performance on this exam. A
B+
B
C+
C
D
F
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