Deck 7: Organohalides: Nucleophilic Substitutions and Eliminations

Question 1

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

Answer 1

1,1,1-triiodomethane

Question 2

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

Answer 2

Question 3

Instructions: Consider the pair of reactions below to answer the following question(s). Refer to instructions. The nucleophile in these reactions is:

A) K⁺
B) alkyl group
C) Br^-
D) I^-

Answer 3

I^-

Question 4

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 5

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

Question 6

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

Question 7

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

Question 8

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

Question 9

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 10

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

Question 11

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

Question 12

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

Question 13

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

Question 14

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

Question 15

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

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

Question 16

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 17

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

Question 18

Instructions: Consider the pair of reactions below to answer the following question(s).
00 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: 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 20

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 21

Instructions:
Draw the structure of the major organic products(s) for each of the following reactions. Indicate the stereochemistry for each reaction when appropriate.

Question 22

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 23

Consider the reaction below to answer the following questions. Draw all the monochlorination products of methylcyclopentane (ignore stereoisomers).

Question 24

Instructions:
Draw the structure of the major organic products(s) for each of the following reactions. Indicate the stereochemistry for each reaction when appropriate.

Question 25

Consider the following compound:

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

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

A)
B)
C)
D)

Question 28

Instructions:
Draw the structure of the major organic products(s) for each of the following reactions. Indicate the stereochemistry for each reaction when appropriate.

Question 29

Consider the reactions below to answer the following questions. a. $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { F } \stackrel { \ominus \mathrm { OH } , \mathrm { H } _ { 2 } \mathrm { O } } { \longrightarrow } \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { OH } + \mathrm { F } \Theta$
or
b. $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { I } \stackrel { \ominus \mathrm { OH } , \mathrm { H } _ { 2 } \mathrm { O } } { \longrightarrow } - \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { OH } + \mathrm { I } \Theta$ The mechanism for these reactions is:
a. $\mathrm{S}_N1$
b. $\mathrm{S}_N2$
c. $\mathrm{E} 1$
d $E2$

Question 30

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 31

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 32

Predict the product of the following reaction:

Question 33

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

Question 34

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 35

Consider the reactions below to answer the following questions. a. $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { F } \stackrel { \ominus \mathrm { OH } , \mathrm { H } _ { 2 } \mathrm { O } } { \longrightarrow } \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { OH } + \mathrm { F } \Theta$
or
b. $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { I } \stackrel { \ominus \mathrm { OH } , \mathrm { H } _ { 2 } \mathrm { O } } { \longrightarrow } - \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { OH } + \mathrm { I } \Theta$ Which reaction would be predicted to be faster? Explain

Question 36

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 37

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 38

Consider the following reaction: a) Draw the prochuct of the reaction. How would you cate gorize this process mechanistically?
b) Which af the following spectral methods caud be used to follow the pargess of the reartigr??
a. NMR spectroscopy
b. Mass spectrometry
c. Infrared spectroscopy
d. UV spectroscopy
e. all of the se
f. a, b, and c onlv

Question 39

Consider the reactions below to answer the following questions. a. $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { F } \stackrel { \ominus \mathrm { OH } , \mathrm { H } _ { 2 } \mathrm { O } } { \longrightarrow } \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { OH } + \mathrm { F } \Theta$
or
b. $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { I } \stackrel { \ominus \mathrm { OH } , \mathrm { H } _ { 2 } \mathrm { O } } { \longrightarrow } - \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { OH } + \mathrm { I } \Theta$ 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

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 41

Instructions:
Draw the structure of the major organic products(s) for each of the following reactions. Indicate the stereochemistry for each reaction when appropriate.

Question 42

Instructions:
Draw the structure of the major organic products(s) for each of the following reactions. Indicate the stereochemistry for each reaction when appropriate.

Question 43

Instructions:
For each substrate below, choose which reaction type is favored. Place the letter of the reaction type in the blank above the substrate.
a. $\mathrm{S}_N1$
b. $\mathrm{S}_N2$
c. $\mathrm{E} 1$
d $E2$ Refer to Instructions.
_____ $\mathrm { R } _ { 2 } \mathrm { CHX } \frac { \text { strong } } { \text { base } } \rightarrow$

Question 44

Instructions:
Draw the structure of the major organic products(s) for each of the following reactions. Indicate the stereochemistry for each reaction when appropriate.

Question 45

Instructions:
For each substrate below, choose which reaction type is favored. Place the letter of the reaction type in the blank above the substrate.
a. $\mathrm{S}_N1$
b. $\mathrm{S}_N2$
c. $\mathrm{E} 1$
d $E2$ Refer to Instructions.
_____ $\mathrm { RCH } _ { 2 } \mathrm { X } \stackrel { \mathrm { Nu } : } { \longrightarrow }$

Question 46

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

Question 47

Grignard Reagents are prepared by reaction of: