Reaction 3. Electrophilic addition of halogens (X₂) to alkenes.X+RX₂RX = Br, ClReagents and conditionsMechanistic detailselectrophilic additionBr2, Cl₂ in CCl4 (or AcOH)room temperaturebromonium or chloronium ion intermediates• anti additionReaction 25. Elimination reaction to form carbon-carbon double bonds.R2XR2BeR4RC-CR4(-HX)HRIR3R3X-leaving group (for example: Cl, Br, I, Tos)B = base (for example: HO, H₂N, t-Buo,C1, H₂O, RNH₂)Reagents and conditionsMechanistic detailsEl mechanism for tertiary or secondary allylic or benzylicsubstrates: the leaving group departs in a unimolecular rate-limiting step, generating the carbocation, which in the secondstep is deprotonated (with base) on the carbon adjacent to thecationc center, yielding the olefin; carbocation rearrangementsmay competevariety of conditions andsolventsusually strong bases favorE2 mechanismE2 mechanism favored by strong bases: the base removes aproton from the carbon adjacent to one bearing the leaving groupin a one-step bimolecular reaction that requires periplanarorientation of the hydrogen and the leaving group (anti-periplanar preferred)competition with substitution reactions (S₁1and SN2) oftenobservedUsually 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 astereoisomer with 2 chiral optically inactive carbons that then reacts with KOH / ethanol (see reaction) that producesan intermediate (B) [C₁4H₁1 Brl that by continuing to react with KOH and heating to 190 degrees Celsius,compound (D) C14H10 is obtaineda) Write the general reaction of this synthesis with the structures of the initial alkene of A, B and Db) Give the reaction mechanism to obtain Ac) Indicate for the absolute configuration of each C* and the IUPAC name of the compoundd) Give the IUPAC and common name of the obtained product D

Answered: Image /qna-images/answer/6497f123-5ed2-4519-9a0f-a10d4e3e755b.jpg

(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

(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

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Concept explainers

Carbohydrates

Carbohydrates are the organic compounds that are obtained in foods and living matters in the shape of sugars, cellulose, and starch. The general formula of carbohydrates is Cn(H2O)2. The ratio of H and O present in carbohydrates is identical to water.

Starch

Starch is a polysaccharide carbohydrate that belongs to the category of polysaccharide carbohydrates.

Mutarotation

The rotation of a particular structure of the chiral compound because of the epimerization is called mutarotation. It is the repercussion of the ring chain tautomerism. In terms of glucose, this can be defined as the modification in the equilibrium of the α- and β- glucose anomers upon its dissolution in the solvent water. This process is usually seen in the chemistry of carbohydrates.

L Sugar

A chemical compound that is represented with a molecular formula C6H12O6 is called L-(-) sugar. At the carbon’s 5th position, the hydroxyl group is placed to the compound’s left and therefore the sugar is represented as L(-)-sugar. It is capable of rotating the polarized light’s plane in the direction anticlockwise. L isomers are one of the 2 isomers formed by the configurational stereochemistry of the carbohydrates.

Question

100%

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

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