Download Addition/E1/E2/SN1/SN2 review Name 1. Which one of the following

Addition/E1/E2/SN1/SN2 review
Name __________________________________
1. Which one of the following halogenoalkanes will most likely react via an SN1 mechanism? (Explain WHY for
an additional point)
a. 1-bromobutane
c. 1-bromo-2-methylpropane
b. 2-bromobutane
d. 2-bromo-2-methylpropane
2. Which of the following reaction mechanisms results in the formation of a carbocation?
a. E1
b. E2
c. SN1
d. SN2
e. addition
3. A substance with an unpaired electron is called a ______________.
a. Molecule
b. Atom
c. Radical
d. Singlet
4. What is the most common reagent used for a reaction of the type mentioned above (involving unpaired
electrons)?
a. UV light
b. electrophile
c. nucleophile
d. strong base
5. Most organic reactions occur in a complex series of steps called a ________________.
a. Reaction Mechanism
c. Reaction Series
b. Reaction Order
d. none of these
6. A substance that loves electrons due to either its excess positive charge or lack of negative charge is called
a(n) ________________.
a. Electrolyte
b. electrophile
c. nucleophile
d. nucleotide
7. A substance that loves positive charge is called a __________________.
a. Electrolyte b. electrophile
c. nucleophile d. nucleotide
8. Which of the following is NOT an example of a nucleophile?
a. an alkene or alkyne
c. a cation
b. an anion
d. a substance with a bare pair of electrons
9. Which of the following halides would be the better leaving group? (Explain WHY for an additional point)
a. Iodide
b. Bromide
c. Chloride
d. Fluoride
10. Which of the following would create the most stable carbocation (according to Zaitsev’s rule)
during an elimination reaction (E1) to produce an alkene?
A
B
C
D
E
11. Which of the following is the BEST solvent to use for the acid-catalyzed dehydrogenation of an alcohol?
a. HCl
b. H2SO4
c. H2O2
d. NaHCO3
12. Which type of reaction results in the formation of an alkene from an alkane?
a. condensation
b. elimination
c. addition
d. substitution
13. Which of the following is the MOST STABLE carbocation?
a. primary
b. secondary
c. tertiary
d. there is no difference
14. What compound is the expected product upon Markovnikov hydrohalogenation with HBr of the alkene shown
below?
?
A
B
C
D
E
15. What is the major product of the following reaction?
?
A
B
C
D
E
16. What is the best reagent to make the following product?
?
A
B
C
17. In an addition reaction to an alkene, the π bond plays the role of:
A) nucleophile
B) electrophile
D
E
C) leaving group
18. What is the major product of the following reaction?
?
19. What is the major product of the following reaction? (Note reagents!!) (Explain WHY you made the
selection you made for an additional point)
?
A
B
C
D
E
20. The expected Markovnikov addition product of HI to 2-methyl-2-butene is: (Draw 2-methyl-2-butene & the
major product for an additional 2 points)
A) 2-iodopentane
D) 2-iodo-1-methylbutane
B) 2-iodo-2-methylbutane
E) 3-iodo-2-methylbutane
C) 1-iodo-2-methylbutane
21. Regioselectivity for _______ reactions follows ________ rule and for _________ reactions, follows ________
rule.
A) Addition, Markovnikov’s, elimination, Zaitsev’s
B) Elimination, Markovnikov’s, addition, Zaitsev’s
C) Addition, Zaitsev’s, elimination, Markovnikov’s
D) Elimination, Zaitsev’s, addition, Markovnikov’s
22. “Dehydrohalogenation” describes a reaction in the course of which a halogen is eliminated and a double bond
is formed. What else is also eliminated?
A) Water
B) hyrdronium ion
C) another halogen
D) hydrogen
23. What is the name of the mechanism used to explain the reaction below: (Explain HOW you arrived at your
Answer) (2 points additional for explanation)
A)
E1
B) E2
C) SN1
D) SN2
24. What is the major product for the following reaction?
A
B
C
D
E
25. Arrange the following alcohols in order of their decreasing reactivity with HBr (most reactive first).
A
A)
B
A>B>C
B)
A>C>B
C
C)
C>A>B
D)
B>C>A
26. Dimethyl ether, or more formally, methoxymethane, is a colorless gas at room temperature, having a
boiling point of -42.1ºC. It is used as an aerosol propellant, as a refrigerant, and as a blowing agent for the
production of some foams. It can also be used as a fuel in diesel engines. What two substances are needed to
make this useful ether?
1)
2)
27. Which factor will best promote substitution versus elimination in the SN1/E1 manifold?
A) A bulkier nucleophile.
C) A less bulky nucleophile.
B) A resonance-stabilized carbocation intermediate.
D) A nonpolar solvent.