Isonitriles (A) are an important class of compounds because of the versatile reactivity of the functional group, enabling the preparation of numerous new compounds and natural products. Isonitriles can be converted to isonitrile dihalides (B), which represents a useful procedure for temporarily hiding the reactivity of an isonitrile (Tetrahedron Lett. 2012, 53, 4536-4537). H,C-C-NEC: H,C-c-N=cC, A B

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
Chapter8: Haloalkanes, Halogenation, And Radical Reactions
Section8.7: Radical Autoxidation
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Isonitriles (A) are an important class of compounds because of the versatile reactivity of the functional group, enabling the
preparation of numerous new compounds and natural products. Isonitriles can be converted to isonitrile dihalides (B), which
represents a useful procedure for temporarily hiding the reactivity of an isonitrile (Tetrahedron Lett. 2012, 53, 4536-4537).
H,C-C-NEC:
H,C-c-N=cc,
A
B
Transcribed Image Text:Isonitriles (A) are an important class of compounds because of the versatile reactivity of the functional group, enabling the preparation of numerous new compounds and natural products. Isonitriles can be converted to isonitrile dihalides (B), which represents a useful procedure for temporarily hiding the reactivity of an isonitrile (Tetrahedron Lett. 2012, 53, 4536-4537). H,C-C-NEC: H,C-c-N=cc, A B
Identify the hybridization state for each highlighted atom in A.
Nitrogen: sp?, Carbon: sp
Nitrogen: sp, Carbon: sp?
O Nitrogen: sp, Carbon: sp
O Nitrogen: sp?, Carbon: sp?
One of the carbon atoms in A exhibits a lone pair. In what type of atomic orbital does this lone pair reside?
sp hybridized orbital
sp? hybridized orbital
O sp hybridized orbital
O sorbital
Predict the C-N-C bond angle in compound A.
i
degree
Transcribed Image Text:Identify the hybridization state for each highlighted atom in A. Nitrogen: sp?, Carbon: sp Nitrogen: sp, Carbon: sp? O Nitrogen: sp, Carbon: sp O Nitrogen: sp?, Carbon: sp? One of the carbon atoms in A exhibits a lone pair. In what type of atomic orbital does this lone pair reside? sp hybridized orbital sp? hybridized orbital O sp hybridized orbital O sorbital Predict the C-N-C bond angle in compound A. i degree
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