H,C CI H2N. CH3 H,SO, C,H,,NO, C,H,NO, + CH,OH - HCI H,0 4. Step 1 Step 2 2.

Pushing Electrons
4th Edition
ISBN:9781133951889
Author:Weeks, Daniel P.
Publisher:Weeks, Daniel P.
Chapter1: Lewis Structures
Section: Chapter Questions
Problem 73EQ
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Part c 

Follow the detailed instructions provided in each of the subsections (a-c):
a) Fill in the following reaction scheme by drawing the structure of intermediate 3 and
products 4-5. Chemical formulas have been added as guidance.
H,C
CI
H,N
CH3
H, SO,
2
CH3
C,H,,NO,
C,H,NO,
CH,OH
1
- HCI
H20
3
Step 1
Step 2
H2N
CH,
OH
C,H,,N,O,
Assign the absolute stereochemistry of the stereogenic centre in compound 1.
b) If the methyl ester in compound 1 was replaced by a carboxylic acid, compound 1 could
react with itself. Can you predict which product will be formed?
H,N
HO.
CH2
C,H;NO,
Step 1
7
c) Using curly arrows, draw the mechanism of Step 2.
Transcribed Image Text:Follow the detailed instructions provided in each of the subsections (a-c): a) Fill in the following reaction scheme by drawing the structure of intermediate 3 and products 4-5. Chemical formulas have been added as guidance. H,C CI H,N CH3 H, SO, 2 CH3 C,H,,NO, C,H,NO, CH,OH 1 - HCI H20 3 Step 1 Step 2 H2N CH, OH C,H,,N,O, Assign the absolute stereochemistry of the stereogenic centre in compound 1. b) If the methyl ester in compound 1 was replaced by a carboxylic acid, compound 1 could react with itself. Can you predict which product will be formed? H,N HO. CH2 C,H;NO, Step 1 7 c) Using curly arrows, draw the mechanism of Step 2.
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