1. Cyclophosphamide is a chemotherapy medication used to treat various types of cancers (i.e. lymphoma, leukemia, and breast cancer). It belongs to a group of cytotoxic alkylating agents known as Nitrogen mustards. The activity of these drugs is attributed to the chloroethylamine groups. NH Cl R R Cyclophosphamide chloroethylamine In this exercise, you will explore the mechanism responsible for the cytotoxic activity of Nitrogen mustards and how it is possible to tune their activity (therefore their toxicity) by modifying their chemical structure. 1.1 Identify and label all nucleophiles/electrophiles in the following reaction. R Cl + N R'-NH2 I R 1.2 Based on your above analysis, draw two possible SN2 reaction mechanisms Intermolecular reaction (reaction between reaction sites on different molecules) Intramolecular reaction (reaction between reaction sites within the same molecule) 1.3 Which of the above reaction will be faster? Why?
1. Cyclophosphamide is a chemotherapy medication used to treat various types of cancers (i.e. lymphoma, leukemia, and breast cancer). It belongs to a group of cytotoxic alkylating agents known as Nitrogen mustards. The activity of these drugs is attributed to the chloroethylamine groups. NH Cl R R Cyclophosphamide chloroethylamine In this exercise, you will explore the mechanism responsible for the cytotoxic activity of Nitrogen mustards and how it is possible to tune their activity (therefore their toxicity) by modifying their chemical structure. 1.1 Identify and label all nucleophiles/electrophiles in the following reaction. R Cl + N R'-NH2 I R 1.2 Based on your above analysis, draw two possible SN2 reaction mechanisms Intermolecular reaction (reaction between reaction sites on different molecules) Intramolecular reaction (reaction between reaction sites within the same molecule) 1.3 Which of the above reaction will be faster? Why?
Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions
Section19.SE: Something Extra
Problem 29VC
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Transcribed Image Text:1. Cyclophosphamide is a chemotherapy medication used to treat various types of
cancers (i.e. lymphoma, leukemia, and breast cancer). It belongs to a group of
cytotoxic alkylating agents known as Nitrogen mustards. The activity of these drugs is
attributed to the chloroethylamine groups.
NH
Cl
R
R
Cyclophosphamide
chloroethylamine
In this exercise, you will explore the mechanism responsible for the cytotoxic activity of
Nitrogen mustards and how it is possible to tune their activity (therefore their toxicity) by
modifying their chemical structure.
Transcribed Image Text:1.1 Identify and label all nucleophiles/electrophiles in the following reaction.
R
Cl
+
N
R'-NH2
I
R
1.2 Based on your above analysis, draw two possible SN2 reaction mechanisms
Intermolecular reaction (reaction between reaction sites on different molecules)
Intramolecular reaction (reaction between reaction sites within the same molecule)
1.3 Which of the above reaction will be faster? Why?
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