If you have already had an eye examination at an ophthalmologist, you probably noticed that you had to use eyedrops at first. The solution is then dripped into the eyes of atropine (the poison of the poison ivy), which dilates the pupils - which makes it possible easier tracking of the fundus. For more complicated procedures they use substances that work longer - for example, tropicamide. Like all similar substances tropicamide also affects the central nervous system and thus became one of the ingredients of the infamous "crocodile" drug. In this task we will look at its synthesis: b) Tropicamide is prepared by the reaction of intermediates IN3 and IN5. The resulting mixture after reaction is diluted with water and slightly warmed. from the mixture, tropicamide crystallizes, and is formed with the general formula C17H20N2O2. Write its structure. c) The IN1 intermediate is a diazonium salt and these are generally unstable in the presence of nucleophiles. Compare the stability (i.e. which substance will be less reactive) of the IN1 intermediate and the nitrogen-free analog (benzenediazonium chloride) in water. Confirm your assumption with resonance structure.

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
icon
Related questions
Question
If you have already had an eye examination at an ophthalmologist, you probably
noticed that you had to use eyedrops at first. The solution is then dripped into the eyes
of atropine (the poison of the poison ivy), which dilates the pupils - which makes it possible
easier tracking of the fundus. For more complicated procedures
they use substances that work longer - for example, tropicamide. Like all similar substances
tropicamide also affects the central nervous system and thus became one of the
ingredients of the infamous "crocodile" drug. In this task we will look at its synthesis:
b) Tropicamide is prepared by the reaction of intermediates IN3 and IN5. The resulting mixture after
reaction is diluted with water and slightly warmed. from the mixture,
tropicamide crystallizes, and is formed with the general formula C17H20N2O2. Write its structure.
c) The IN1 intermediate is a diazonium salt and these are generally unstable
in the presence of nucleophiles. Compare the stability (i.e. which substance will be less
reactive) of the IN1 intermediate and the nitrogen-free analog
(benzenediazonium chloride) in water. Confirm your assumption with resonance
structure.
NO₂
NH₂
D, E
0^q±§~§-3-6
N₂
N₂
IN3
O, P
Q. R
1: NaH
(2 equivalents)
2: AA
Ph
O
B.C
HO.
AcO
M, N
S. T
3
COOH
IN4
HO, CN
K₂CO₂
COOH water
AB
K.L
U, V
IN2
COOH
AcO
F, G
NH₂!
COCI
INS:
N₂CI
IN1
TSO CN
1: J
water
W
teplo
H
CN
COOH
CN
Ne
CN
1: X, Y
2: H
Transcribed Image Text:If you have already had an eye examination at an ophthalmologist, you probably noticed that you had to use eyedrops at first. The solution is then dripped into the eyes of atropine (the poison of the poison ivy), which dilates the pupils - which makes it possible easier tracking of the fundus. For more complicated procedures they use substances that work longer - for example, tropicamide. Like all similar substances tropicamide also affects the central nervous system and thus became one of the ingredients of the infamous "crocodile" drug. In this task we will look at its synthesis: b) Tropicamide is prepared by the reaction of intermediates IN3 and IN5. The resulting mixture after reaction is diluted with water and slightly warmed. from the mixture, tropicamide crystallizes, and is formed with the general formula C17H20N2O2. Write its structure. c) The IN1 intermediate is a diazonium salt and these are generally unstable in the presence of nucleophiles. Compare the stability (i.e. which substance will be less reactive) of the IN1 intermediate and the nitrogen-free analog (benzenediazonium chloride) in water. Confirm your assumption with resonance structure. NO₂ NH₂ D, E 0^q±§~§-3-6 N₂ N₂ IN3 O, P Q. R 1: NaH (2 equivalents) 2: AA Ph O B.C HO. AcO M, N S. T 3 COOH IN4 HO, CN K₂CO₂ COOH water AB K.L U, V IN2 COOH AcO F, G NH₂! COCI INS: N₂CI IN1 TSO CN 1: J water W teplo H CN COOH CN Ne CN 1: X, Y 2: H
Expert Solution
steps

Step by step

Solved in 2 steps with 1 images

Blurred answer
Knowledge Booster
Gravimetric Analysis
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY