N=N=N CH3CH2CH=CH2 I-N=N=N CH3CH2CHCH2I

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter31: Immunochemistry
Section: Chapter Questions
Problem 31.75P
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Iodine azide, IN3 , adds to alkenes by an electrophilic mechanism similar to that of bromine. If a monosubstituted alkene such as 1-butene is used, only one product results:

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(a) Add lone-pair electrons to the structure shown for IN3 , and draw a second resonance form for the molecule.
(b) Calculate formal charges for the atoms in both resonance structures you drew for IN3 in part (a).
(c) In light of the result observed when Ι�3 adds to 1-butene, what is the polarity of the I—N3 bond? Propose a mechanism for the reaction using curved arrows to show the electron flow in each step

N=N=N
CH3CH2CH=CH2
I-N=N=N
CH3CH2CHCH2I
Transcribed Image Text:N=N=N CH3CH2CH=CH2 I-N=N=N CH3CH2CHCH2I
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