Interpretation: The mechanism for the addition of bromine water to cyclopentene and explanation regarding formation of enantiomer is to be stated.
Concept introduction: The general steps for the formation of halohydrin are stated below:
- The first step is the attack of halide ion to form a halonium ion.
- The second step is the attack of water to opens the halonium ion.
- The last step is deprotonation to give the halohydrin product.
Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on
Anti stereochemistry is the addition of any atom from the opposite faces of the double bond of
To determine: The mechanism for the addition of bromine water to cyclopentene and explanation regarding formation of enantiomer.
Trending nowThis is a popular solution!
Chapter 8 Solutions
Organic Chemistry (9th Edition)
- Claisen rearrangement of an allyl phenyl ether with substituent groups in both ortho positions leads to the formation of a para-substituted product. Propose a mechanism for the following rearrangement.arrow_forwardBicyclo-2,5-heptadiene can be prepared in two steps from cyclopentadiene and vinyl chloride. Provide a mechanism for each step.arrow_forwardPropose a synthesis to convert 1-methylcyclopentene B to the cyclic ester C. Show all intermediates, and reagents necessary for each step.arrow_forward
- How to synthesize 1-iodo-2-methylcyclopentane to 1-methylcyclopentanol? Show mechanismsarrow_forwardPropose a mechanism for the reaction of 1-methylcyclopentene with bromine water.arrow_forwardDraw the keto and enol forms of 3,3-dimethylbutan-2-one, circle the more stable tautomer, and propose a mechanism for the conversion of one tautomer to the other in acidic conditions.arrow_forward
- a. Propose a mechanism for the following reaction. (Hint: An electrocyclic reaction is followed by a Diels–Alder reaction.)b. What would be the product if trans-2-butene were used instead of ethene?arrow_forwardPropose a mechanism for addition of HI to 1-methylcyclohexene to give 1-iodo1-methylcyclohexane. Which step in your mechanism is rate-determining?arrow_forwardOn treatment with HBr, vinylcyclohexane undergoes addition and rearrangement to yield 1-bromo-l-ethylcyclohexane. Using curved arrows, propose a mechanism to account for this result.arrow_forward
- Propose a mechanism for this reaction. Account for both its regioselectivity and stereoselectivity.arrow_forwardA step in a synthesis of PGE1 (prostaglandin E1, alprostadil) is the reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Propose a mechanism for formation of this bromolactone and account for the observed stereochemistry of each substituent on the cyclohexane ring. Alprostadil is used as a temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation.arrow_forwardPropose a mechanism for this isomerization.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning