(E)-1-2- Diphenylethene reacts with Br 2 /CCI4 (see reaction) the reaction product is obtained (A) is a stereoisomer with 2 chiral optically inactive carbons that then reacts with KOH / ethanol (see reaction) that produces an intermediate (B) [C₁4H₁1 Brl that by continuing to react with KOH and heating to 190 degrees Celsius, compound (D) C14H10 is obtained a) Write the general reaction of this synthesis with the structures of the initial alkene of A, B and D b) Give the reaction mechanism to obtain A c) Indicate for the absolute configuration of each C* and the IUPAC name of the compound d) Give the IUPAC and common name of the obtained product D

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Chapter1: Chemical Foundations
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Reaction 3. Electrophilic addition of halogens (X₂) to alkenes.
X
+
R
X₂
R
X = Br, Cl
Reagents and conditions
Mechanistic details
electrophilic addition
Br2, Cl₂ in CCl4 (or AcOH)
room temperature
bromonium or chloronium ion intermediates
• anti addition
Reaction 25. Elimination reaction to form carbon-carbon double bonds.
R2
X
R2
Be
R4
RC-CR4
(-HX)
H
RI
R3
R3
X-leaving group (for example: Cl, Br, I, Tos)
B = base (for example: HO, H₂N, t-Buo,C1, H₂O, RNH₂)
Reagents and conditions
Mechanistic details
El mechanism for tertiary or secondary allylic or benzylic
substrates: the leaving group departs in a unimolecular rate-
limiting step, generating the carbocation, which in the second
step is deprotonated (with base) on the carbon adjacent to the
cationc center, yielding the olefin; carbocation rearrangements
may compete
variety of conditions and
solvents
usually strong bases favor
E2 mechanism
E2 mechanism favored by strong bases: the base removes a
proton from the carbon adjacent to one bearing the leaving group
in a one-step bimolecular reaction that requires periplanar
orientation of the hydrogen and the leaving group (anti-
periplanar preferred)
competition with substitution reactions (S₁1and SN2) often
observed
Usually the most substituted olefin is the major product
(Zaitsev's rule)
Transcribed Image Text:Reaction 3. Electrophilic addition of halogens (X₂) to alkenes. X + R X₂ R X = Br, Cl Reagents and conditions Mechanistic details electrophilic addition Br2, Cl₂ in CCl4 (or AcOH) room temperature bromonium or chloronium ion intermediates • anti addition Reaction 25. Elimination reaction to form carbon-carbon double bonds. R2 X R2 Be R4 RC-CR4 (-HX) H RI R3 R3 X-leaving group (for example: Cl, Br, I, Tos) B = base (for example: HO, H₂N, t-Buo,C1, H₂O, RNH₂) Reagents and conditions Mechanistic details El mechanism for tertiary or secondary allylic or benzylic substrates: the leaving group departs in a unimolecular rate- limiting step, generating the carbocation, which in the second step is deprotonated (with base) on the carbon adjacent to the cationc center, yielding the olefin; carbocation rearrangements may compete variety of conditions and solvents usually strong bases favor E2 mechanism E2 mechanism favored by strong bases: the base removes a proton from the carbon adjacent to one bearing the leaving group in a one-step bimolecular reaction that requires periplanar orientation of the hydrogen and the leaving group (anti- periplanar preferred) competition with substitution reactions (S₁1and SN2) often observed Usually the most substituted olefin is the major product (Zaitsev's rule)
(E) -1-2- Diphenylethene reacts with Br2 /CCI 4 (see reaction) the reaction product is obtained (A) is a
stereoisomer with 2 chiral optically inactive carbons that then reacts with KOH / ethanol (see reaction) that produces
an intermediate (B) [C₁4H₁1 Brl that by continuing to react with KOH and heating to 190 degrees Celsius,
compound (D) C14H10 is obtained
a) Write the general reaction of this synthesis with the structures of the initial alkene of A, B and D
b) Give the reaction mechanism to obtain A
c) Indicate for the absolute configuration of each C* and the IUPAC name of the compound
d) Give the IUPAC and common name of the obtained product D
Transcribed Image Text:(E) -1-2- Diphenylethene reacts with Br2 /CCI 4 (see reaction) the reaction product is obtained (A) is a stereoisomer with 2 chiral optically inactive carbons that then reacts with KOH / ethanol (see reaction) that produces an intermediate (B) [C₁4H₁1 Brl that by continuing to react with KOH and heating to 190 degrees Celsius, compound (D) C14H10 is obtained a) Write the general reaction of this synthesis with the structures of the initial alkene of A, B and D b) Give the reaction mechanism to obtain A c) Indicate for the absolute configuration of each C* and the IUPAC name of the compound d) Give the IUPAC and common name of the obtained product D
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