5. Trinitrotoluene or TNT is, perhaps, the best-known explosive (in classic cartoons, for example, Wile E. Coyote unsuccessfully employs TNT against the Roadrunner many times). The synthesis of TNT starting with toluene (PhCH) is straightforward even if the isolation of the final product requires careful planning and a gentle touch (otherwise, KABOOM!). Answer the following questions about the synthesis of TNT starting with toluene. a. Name the reagent(s) required to add the nitro groups to toluene. [2 pts] b. Structures I-III are the possible isomers after the addition of a single nitro group. Which isomer(s) is/are the major reaction intermediates after addition of the first nitro group to tolu- ene? Write the letter (A-F) corresponding to your answer in the box. [3 pts] AB I alone B II alone O₂N O₂N NO2 I II III с III alone E I and III D I and II F II and III c. Structures a–f are the possible isomers after the addition of two nitro groups. Which isomers are the major reaction intermediates after addition of two nitro groups to toluene? Write the letter (A-I) corresponding to your answer in the box. [3 pts] O₂N. O₂N. O₂N O₂N. NO2 O₂N O₂N a NO2 O₂N NO2 NO2 NO₂ b с e ABC a and b D b and d G c and f a and e E c and d H d and f C b and c F c and e | e and f
5. Trinitrotoluene or TNT is, perhaps, the best-known explosive (in classic cartoons, for example, Wile E. Coyote unsuccessfully employs TNT against the Roadrunner many times). The synthesis of TNT starting with toluene (PhCH) is straightforward even if the isolation of the final product requires careful planning and a gentle touch (otherwise, KABOOM!). Answer the following questions about the synthesis of TNT starting with toluene. a. Name the reagent(s) required to add the nitro groups to toluene. [2 pts] b. Structures I-III are the possible isomers after the addition of a single nitro group. Which isomer(s) is/are the major reaction intermediates after addition of the first nitro group to tolu- ene? Write the letter (A-F) corresponding to your answer in the box. [3 pts] AB I alone B II alone O₂N O₂N NO2 I II III с III alone E I and III D I and II F II and III c. Structures a–f are the possible isomers after the addition of two nitro groups. Which isomers are the major reaction intermediates after addition of two nitro groups to toluene? Write the letter (A-I) corresponding to your answer in the box. [3 pts] O₂N. O₂N. O₂N O₂N. NO2 O₂N O₂N a NO2 O₂N NO2 NO2 NO₂ b с e ABC a and b D b and d G c and f a and e E c and d H d and f C b and c F c and e | e and f
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter23: Amines
Section: Chapter Questions
Problem 23.67P
Related questions
Question
![5. Trinitrotoluene or TNT is, perhaps, the best-known explosive (in classic cartoons, for example,
Wile E. Coyote unsuccessfully employs TNT against the Roadrunner many times).
The synthesis of TNT starting with toluene (PhCH) is straightforward even if the isolation of the
final product requires careful planning and a gentle touch (otherwise, KABOOM!).
Answer the following questions about the synthesis of TNT starting with toluene.
a. Name the reagent(s) required to add the nitro groups to toluene. [2 pts]
b. Structures I-III are the possible isomers after the addition of a single nitro group. Which
isomer(s) is/are the major reaction intermediates after addition of the first nitro group to tolu-
ene? Write the letter (A-F) corresponding to your answer in the box. [3 pts]
AB
I alone
B II alone
O₂N
O₂N
NO2
I
II
III
с
III alone
E
I and III
D
I and II
F
II and III
c. Structures a–f are the possible isomers after the addition of two nitro groups. Which isomers
are the major reaction intermediates after addition of two nitro groups to toluene? Write the
letter (A-I) corresponding to your answer in the box. [3 pts]
O₂N.
O₂N.
O₂N
O₂N.
NO2
O₂N
O₂N
a
NO2
O₂N
NO2
NO2
NO₂
b
с
e
ABC
a and b
D
b and d
G
c and f
a and e
E
c and d
H
d and f
C
b and c
F
c and e
|
e and f](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F39f6380b-55e3-47ff-8091-2f92e2b304db%2F6e40723a-3f3b-4603-936f-abb63cc5b1f2%2Fb86bzsm_processed.jpeg&w=3840&q=75)
Transcribed Image Text:5. Trinitrotoluene or TNT is, perhaps, the best-known explosive (in classic cartoons, for example,
Wile E. Coyote unsuccessfully employs TNT against the Roadrunner many times).
The synthesis of TNT starting with toluene (PhCH) is straightforward even if the isolation of the
final product requires careful planning and a gentle touch (otherwise, KABOOM!).
Answer the following questions about the synthesis of TNT starting with toluene.
a. Name the reagent(s) required to add the nitro groups to toluene. [2 pts]
b. Structures I-III are the possible isomers after the addition of a single nitro group. Which
isomer(s) is/are the major reaction intermediates after addition of the first nitro group to tolu-
ene? Write the letter (A-F) corresponding to your answer in the box. [3 pts]
AB
I alone
B II alone
O₂N
O₂N
NO2
I
II
III
с
III alone
E
I and III
D
I and II
F
II and III
c. Structures a–f are the possible isomers after the addition of two nitro groups. Which isomers
are the major reaction intermediates after addition of two nitro groups to toluene? Write the
letter (A-I) corresponding to your answer in the box. [3 pts]
O₂N.
O₂N.
O₂N
O₂N.
NO2
O₂N
O₂N
a
NO2
O₂N
NO2
NO2
NO₂
b
с
e
ABC
a and b
D
b and d
G
c and f
a and e
E
c and d
H
d and f
C
b and c
F
c and e
|
e and f
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