Treatment of the following stereoisomer of 1-bromo-1,2-diphenylpropane with sodium ethoxide in ethanol gives a single stereoisomer of 1,2-diphenylpropene. H3C H CoH5 CH3CH20 Na* CH3CH2OH C6H5 Br Draw the E2 elimination product of the reaction. Take into account that the starting stereochemistry affects the resulting double bond stereochemistry. • Consider E/Z stereochemistry of alkenes. • Do not show stereochemistry in other cases. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one.

Treatment of the following stereoisomer of 1-bromo-1,2-diphenylpropane with sodium ethoxide in ethanol gives a single stereoisomer of 1,2-diphenylpropene. H3C H CoH5 CH3CH20 Na* CH3CH2OH C6H5 Br Draw the E2 elimination product of the reaction. Take into account that the starting stereochemistry affects the resulting double bond stereochemistry. • Consider E/Z stereochemistry of alkenes. • Do not show stereochemistry in other cases. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter9: Nucleophilic Substitution And Β-elimination

Section: Chapter Questions

Problem 9.39P: Following are diastereomers (A) and (B) of 3-bromo-3,4-dimethylhexane. On treatment with sodium...

See similar textbooks

Similar questions

Following are diastereomers (A) and (B) of 3-bromo-3,4-dimethylhexane. On treatment with sodium ethoxide in ethanol, each gives 3,4-dimethyl-3-hexene as the major product. One diastereomer gives the E alkene, and the other gives the Z alkene. Which diastereomer gives which alkene? Account for the stereoselectivity of each -elimination.
Consider the E1 reaction of 3-bromo-2-cyclohexyl-butane. How many elimination products are possible? Include (E)/(Z) isomers as separate products.
What would the major organic reaction product be from the reaction of 1-bromo-1-methylcyclopentane withsodium hydroxide? Would the elimination reaction outcome be affected if a student accidentally adds sodium tertbutoxide instead of sodium hydroxide?
Provide the product most likely to form from reaction of each reagent with 1-methylcyclohexene. You may ingore stereochemistry for this question. Br2 H-Br H-Br, PhC(O)OOC(O)Ph N-bromosuccinimide, PhC(O)OOC(O)Ph A. B. C. D.
2-Methyl-2-butene reacts with HBr in the presence of peroxide to give a. a secondary alkyl bromide. b. a primary alkyl bromide. c. a tertiary alkyl bromide. d. a vicinal dibromide.
Draw structural formulas for the isomeric carbocation intermediates formed on treatment of each alkene with HCl. Label each carbocation 1°, 2°, or 3° and state which of the isomeric carbocations forms more readily.
When 1 mole of buta-1,3-diene reacts with 1 mole of HBr, both 3-bromobut-1-ene and 1-bromobut-2-ene are formed. Propose a mechanism to account for this mixture of products.
Explain the stereochemistry of E2 eliminations to form alkenes, and predict the products of E1 reactions on stereoisomers and on cyclohexane systems.
When it is treated with sodium ethoxide in deuterated ethanol (C2H5OD), cyclopentadiene exchanges all of its hydrogens for deuterium. Draw a structure for the intermediate in this reaction with all protons (no deuterons).
For each reaction, give the expected substitution product and predict whether the mechanism will be first order (SN1) or second order (SN2): a) 2-chloro-2-methylbutane + CH3COOH b) isobutyl bromide + NaOMe c) 1-iodo-1-methylcyclohexane + CH3CH2OH Q3. 2-Bromopentane, when treated with ‎ alcoholic KOH yields a mixture of three alkenes A, B and C. Identify A, B and C. Which is predominant?
What is the most probable elimination product when 4-chlorocyclohexene is reacted with alcoholic KOH? 1,3-cyclohexadiene 1,4-cyclohexadiene Cyclohexane Cyclohexene
The expected major product from the treatment of 1-pentyne with 1 equivalent of HBr is: 1,2-dibromopentane 1-bromo-1-pentene 2-bromo-1-pentene 1,1-dibromopentane 2,2-dibromopentane