This synthesis scheme was designed using the reaction roadmaps. (Reaction roadmaps allow you to "navigate" between the different functional groups and their behavior in chemical reactions.) HA -1 compound c . compound b W compound a compound f HH compound e compound d Reagents a. HBr b. c. H₂O, H₂SO4 d. Br₂ e. Cl₂ f. 9. h. i. j. HBr, H₂O₂, hv H₂, Pd Br₂, H₂O Cl₂, H₂O OsO4 then NaHSO3 . Use the wedge/hash bond tools to indicate stereochemistry where it exists. . If there are alternative structures, draw the most stable one. 2 equivalents of NaNH₂ H₂, Lindlar's catalyst Hg(OAc)2, H₂O then NaBH4 k. BH3 then H₂O₂, NaOH I. O, then (CH3)2S In this synthesis, reagents from the table are used to carry out the indicated steps (shown in blue). In the box below, draw the structure of compound d. If the reaction produces a racemic mixture, draw both stereoisomers. Separate structures with + signs from the drop-down menu. m. n. O. Na/NH3 p. H₂SO4, HgSO4 q. (sia) BH then H₂O₂, NaOH r. 1 equivalent of NaNH₂ S. NBS, hv t. U. V. HCI w. (CH3)3COK' Br₂, hv Cl₂, hv
Reactive Intermediates
In chemistry, reactive intermediates are termed as short-lived, highly reactive atoms with high energy. They rapidly transform into stable particles during a chemical reaction. In specific cases, by means of matrix isolation and at low-temperature reactive intermediates can be isolated.
Hydride Shift
A hydride shift is a rearrangement of a hydrogen atom in a carbocation that occurs to make the molecule more stable. In organic chemistry, rearrangement of the carbocation is very easily seen. This rearrangement can be because of the movement of a carbocation to attain stability in the compound. Such structural reorganization movement is called a shift within molecules. After the shifting of carbocation over the different carbon then they form structural isomers of the previous existing molecule.
Vinylic Carbocation
A carbocation where the positive charge is on the alkene carbon is known as the vinyl carbocation or vinyl cation. The empirical formula for vinyl cation is C2H3+. In the vinyl carbocation, the positive charge is on the carbon atom with the double bond therefore it is sp hybridized. It is known to be a part of various reactions, for example, electrophilic addition of alkynes and solvolysis as well. It plays the role of a reactive intermediate in these reactions.
Cycloheptatrienyl Cation
It is an aromatic carbocation having a general formula, [C7 H7]+. It is also known as the aromatic tropylium ion. Its name is derived from the molecule tropine, which is a seven membered carbon atom ring. Cycloheptatriene or tropylidene was first synthesized from tropine.
Stability of Vinyl Carbocation
Carbocations are positively charged carbon atoms. It is also known as a carbonium ion.
![This synthesis scheme was designed using the reaction roadmaps. (Reaction roadmaps allow you to "navigate" between the different functional groups and
their behavior in chemical reactions.)
compound c
compound b
●
W
compound a
compound f
MAVI
compound e
m
compound d
Reagents
HBr
HBr, H₂O₂, hv
a.
b.
c. H₂O, H₂SO4
d. Br₂
e. Cl₂
f.
H₂, Pd
Br₂, H₂O
Cl₂, H₂O
OsO4 then NaHSO3
#[ ] در
g.
h.
i.
j.
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
• If there are alternative structures, draw the most stable one.
• If the reaction produces a racemic mixture, draw both stereoisomers.
Separate structures with + signs from the drop-down menu.
k.
I.
m.
n.
O.
p.
Hg(OAc)2, H₂O then NaBH4
BH3 then H₂O₂, NaOH
O3 then (CH3)2S
In this synthesis, reagents from the table are used to carry out the indicated steps (shown in blue). In the box below, draw the structure of compound d.
q.
r.
2 equivalents of NaNH₂
H2, Lindlar's catalyst
Na/NH3
H₂SO4, HgSO4
(sia)2BH then H₂O₂, NaOH
1 equivalent of NaNH₂
NBS, hv
Br₂, hv
Cl₂, hv
HCI
S.
t.
u.
V.
W. (CH3)3CO'K+
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