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.
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Chapter 8 Solutions
EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
- When cyclohexene is reacted with hydrobromic acid in acetic acid, the major product is bromocyclohexane. There is a small amount of cyclohexyl acetate formed. What is the mechanism that forms both compounds? What is the purification procedure that isolates both compounds?arrow_forwardCompound A is an alkyne that reacts with two equivalents of H2 in the presence of Pd to give 2,4,6-trimethyloctane. Draw the structure of compound A.arrow_forwardIf phenoxide ion is allowed to react with 1-bromopentane, pentyl phenyl ether is obtained. However, if cyclohexane is used as the alkyl halide, the major products are phenol and cyclohexene. Explain how these products were formed.arrow_forward
- If 1-bromopentane is heated in acetone containing NaOH, what is the alkane produced? Draw and explain the step-by-step mechanism of the production of the compoundarrow_forward6) 25pts. Draw the structure of the major alkene product (or products) formed by treatment of each of the following haloalkanes with sodium ethoxide in ethanol. Assume the mechanism is E2 elimination. t-BuO K t-BUOH Br CH3 Eto Na F ETOH CH2CH3 CI H- Eto Na -CH2CH3 ELOH H- ČH3 Br Eto Na ELOH CH3 CI, H Eto Na CH2CH3 H3C H D ELOHarrow_forwardWhen cyclohexene is treated with m-chloroperbenzoic acid and H,0, trans-cyclohexane-1,2-diol is produced. Propose a mechanism for this reaction, accounting for the observed stereochemistry. Hint: Recall what a МСРВА + Enantiomer H2O "OH peroxyacid does to an alkene.arrow_forward
- The following compound undergoes an intramolecular reaction to form ethene and a product with a five-membered ring. Identify the product and the catalyst used to carry out the reaction.arrow_forwardDraw all of the substitution and elimination products formed from thegiven alkyl halide with each reagent: (a) CH3OH; (b) KOH. Indicate thestereochemistry around the stereogenic centers present in the products,as well as the mechanism by which each product is formed.arrow_forwardThe addition of dilute H2SO4 in the presence of H9SO4 to 1-butyne produces an alcohol O an enol an enol followed by a ketone O an enol followed by a aldehydearrow_forward
- Arrange the alkenes in each set in order of increasing rate of reaction with HI and explain the basis for your ranking. Draw the structural formula of the major product formed in each case.arrow_forwardDraw the product formed when CH3CH2C=CH is treated with each of the following sets of reagents: (a) H2O, H2SO4, HgSO4; and (b) R2BH, followed by H2O2, HO−.arrow_forwardOne compound that contributes to the “seashore smell” at beaches in Hawai‘i is dictyopterene D', a component of a brown edible seaweed called limu lipoa. Hydrogenation of dictyopterene D' with excess H2 in the presence of a Pd catalyst forms butylcycloheptane. Ozonolysis with O3 followed by (CH3)2S forms CH2(CHO)2, HCOCH2CH(CHO)2, and CH3CH2CHO. What are possible structures of dictyopterene D'?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning