Deck 7: Organohalides: Nucleophilic Substitutions and Eliminations

Question 1

Instructions: Provide a IUPAC name for each of the following alkyl halides.
Name: (Halothane)

Answer 1

2-bromo-2-chloro-1,1,1-trifluoroethane

Question 2

Instructions: Circle the correct response in each set below.
Refer to instructions. The least reactive compound in an S_N1 reaction.

Answer 2

Question 3

Instructions: Provide a IUPAC name for each of the following alkyl halides.
Name:

Answer 3

1-bromo-1-chloroethane

Question 4

Instructions: For each question, draw a structure corresponding to the given name.
Draw:
1,2-dichloro-1,1,2,2-tetrafluoroethane (Cryofluorane)

Question 5

Instructions: For each question, draw a structure corresponding to the given name.
Draw:
(S)-2-bromobutane

Question 6

Instructions: Consider the reaction below to answer the following question.

Refer to instructions. The mechanism for this reaction is:

A) S_N2
B) E2
C) S_N1
D) E1

Question 7

Instructions: Consider the pair of reactions below to answer the following question(s).
a.
or
b.

-Refer to instructions. The nucleophile in these reactions is:

A) K⁺
B) alkyl group
C) Br^-
D) I^-

Question 8

Instructions: For each question, draw a structure corresponding to the given name.
Draw:
3-iodoprop-1-ene

Question 9

Instructions: Consider the pair of reactions below to answer the following question(s).
a.
or
b.
Refer to instructions. The mechanism for these reactions is:

A) S_N2
B) E2
C) S_N1
D) E1

Question 10

Instructions: Consider the reaction below to answer the following question(s).

Refer to instructions. Write the product that results from the indicated electron flow in the reaction, showing any resulting stereochemistry

Question 11

Instructions: Circle the correct response in each set below.
Refer to instructions. The least reactive compound in an S_N2 reaction. Explain your choice.

Question 12

Instructions: For each question, provide structures for the reactants, intermediates, or products, as indicated. Draw the structures in the boxes provided.
Draw:

Question 13

Instructions: Provide a IUPAC name for each of the following alkyl halides.
Name:
The solvents: CCl₄ and CH₂Cl₂

Question 14

Instructions: Consider the reaction below to answer the following question(s).

Refer to instructions. Compound C is the:

A) S_N2 product
B) S_N1 product
C) E2 product
D) E1 product

Question 15

Instructions: Consider the reaction below to answer the following question(s).

Refer to instructions. Compound B is the:

A) S_N2 product
B) S_N1 product
C) E2 product
D) E1 product

Question 16

Instructions: Provide a IUPAC name for each of the following alkyl halides.
Name:

Question 17

Instructions: For each question, draw a structure corresponding to the given name.
Draw:
trans-1-sec-butyl-3-chlorocyclohexane

Question 18

Instructions: Consider the pair of reactions below to answer the following question(s).
a.
or
b.

-Refer to instructions. The alkyl bromide starting materials in these reactions are classified as:

A) 3 $\degree$
B) 2 $\degree$
C) 1 $\degree$
D) 4 $\degree$

Question 19

Instructions: Provide a IUPAC name for each of the following alkyl halides.
Name:
CHI₃ (iodoform)

Question 20

Instructions: For each question, provide structures for the reactants, intermediates, or products, as indicated. Draw the structures in the boxes provided.
Draw:

Question 21

Instructions: Consider the reaction below to answer the following question(s).

Refer to instructions. The mechanism of this reaction is:

A) S_N1
B) S_N2
C) E1
D) E2

Question 22

Which is most reactive in an S_N1 reaction? Explain your choice.

A)
B)CH₃I
C)
D)
E)

Question 23

Propose a synthesis of the following compound from the given starting material and any inorganic reagents necessary.

Question 24

Grignard Reagents are prepared by reaction of:

A) an alkyl halide with magnesium in ether solvent.
B) an alkyl halide with cuprous iodide in ether solvent.
C) an alkyl halide with lithium metal in ether solvent.
D) all of the above reactions prepare Grignard reagents.

Question 25

Instructions:
For each substrate below, choose which reaction type is favored. Place the letter of the reaction type in the blank above the substrate.

Refer to Instructions.
_____

A)S_N1
B)S_N2
C)E1
D)E2

Question 26

Which mechanism is favored by the reaction of a secondary alkyl bromide with potassium t-butoxide?

A) S_N1
B) S_N2
C) E1
D) E1_CB
E) E2

Question 27

Consider the reactions below to answer the following questions.



Which reaction would be predicted to be faster? Explain.

Question 28

Instructions: Consider the reaction below to answer the following question(s).

Refer to instructions. Draw a Newman projection of the reactive conformation of the starting material.

Question 29

Which of the following statements about an S_N1 reaction is true?

A) the reaction occurs in one-step
B) there is no effect on reaction rate by nucleophile
C) primary alkyl halides react faster than secondary alkyl halides
D) the reaction proceeds with inversion of stereochemistry
E) the reaction is favored by aprotic solvents

Question 30

Which of the following represents the transition state of the S_N2 reaction between methyl iodide and ammonia?

A)
B)
C)
D)

Question 31

Instructions:
For each substrate below, choose which reaction type is favored. Place the letter of the reaction type in the blank above the substrate.

Refer to Instructions.
_____

A)S_N1
B)S_N2
C)E1
D)E2

Question 32

Instructions:
For each substrate below, choose which reaction type is favored. Place the letter of the reaction type in the blank above the substrate.

Refer to Instructions.
_____

A)S_N1
B)S_N2
C)E1
D)E2

Question 33

Which of the following statements about an S_N2 reaction is true?

A) the reaction occurs in two steps
B) rate = k[RX]
C) stabilization of R⁺ is important
D) the reaction causes racemization
E) the reaction is favored by aprotic solvents

Question 34

What is the IUPAC name of the following compound?

A) (R)-2-bromo-2-vinylpentane
B) (S)-2-bromo-2-vinylpentane
C) (S)-3-bromo-3-propylbut-1-ene
D) (R)-3-bromo-3-methylhex-1-ene

Question 35

Which mechanism is favored by the reaction of a tertiary alkyl chloride with ethanol?

A) S_N1
B) S_N2
C) E1
D) E1_CB
E) E2

Question 36

What is the rate law for the E2 reaction of an alkyl halide (RX) with sodium ethoxide (NaOEt) in ethanol solvent (EtOH)?

A) rate = k[RX]
B) rate = k[RX]²
C) rate = k[RX][Na⁺]
D) rate = k[RX][OEt^-]
E) rate = k[OEt^-]

Question 37

Consider the reactions below to answer the following questions.


The mechanism for these reactions is:

A) S_N1
B) S_N2
C) E1
D) E2

Question 38

Predict the product of the following reaction:

Question 39

Halving the concentration of hydroxide in these reactions:

A)causes the reaction mechanism to change
B)halves the rate of reaction
C)has no effect on the rate of reaction
D)doubles the rate of reaction

Question 40

Draw all the monochlorination products of methylcyclopentane (ignore stereoisomers).