1-Chloro-4-isopropylcyclohexane exists as two stereoisomers: one cis and one trans. Treatment of either isomer with sodium ethoxide in ethanol gives 4-isopropylcyclohexene by an E2 reaction. CH,CH,O Na* CI CH,CH,OH 1-Chloro-4- 4-Isopropylcyclohexene isopropylcyclohexane The cis isomer undergoes E2 reaction several orders of magnitude faster than the trans isomer. How do you account for this experimental observation?

1-Chloro-4-isopropylcyclohexane exists as two stereoisomers: one cis and one trans. Treatment of either isomer with sodium ethoxide in ethanol gives 4-isopropylcyclohexene by an E2 reaction. CH,CH,O Na* CI CH,CH,OH 1-Chloro-4- 4-Isopropylcyclohexene isopropylcyclohexane The cis isomer undergoes E2 reaction several orders of magnitude faster than the trans isomer. How do you account for this experimental observation?

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

Section9.7: Experimental Evidence For E1 And E2 Mechanisms

Problem 9.7P

See similar textbooks

Similar questions

When buta-1,3-diene (CH2 = CH – CH = CH2) is treated with HBr, two constitutional isomers are formed, CH3CHBrCH = CH2 and BrCH2CH = CHCH3. Draw a stepwise mechanism that accounts for the formation of both products.
Which stereoisomer of 3-hexene forms (3S,4S)-4-bromo-3-hexanol and (3R,4R)-4-bromo-3-hexanol when it reacts with Br2 and H2O?
Draw the product obtained when cis-2-butene is treated first with Br2 in CH2Cl2, second with NaNH2 in NH3, and then finally with Li in NH3.
Oximene and myrcene, two hydrocarbons isolated from alfalfa that have the molecular formula C10H16, both yield 2,6- dimethyloctane when treated with H2 and a Pd catalyst. Ozonolysis of oximene forms (CH3)2C = O, CH2 = O, CH2(CHO)2, and CH3COCHO. Ozonolysis of myrcene yields (CH3)2C = O, CH2 = O, (two equiv), and HCOCH2CH2COCHO. Identify the structures of oximene and myrcene.
Account for the regioselectivity and stereoselectivity observed when 1-methylcyclopentene is treated with reagent Q.Hg(OAc)2 in H2O
A chemist allows some pure (2S,3R)-3-bromo-2,3-diphenylpentane to react with a solution of sodium ethoxide(NaOCH2CH3) in ethanol. The products are two alkenes: A (cis-trans mixture) and B, a single pure isomer. Under thesame conditions, the reaction of (2S,3S)-3-bromo-2,3-diphenylpentane gives two alkenes, A (cis-trans mixture) and C.Upon catalytic hydrogenation, all three of these alkenes (A, B, and C) give 2,3-diphenylpentane. Determine the structuresof A, B, and C; give equations for their formation; and explain the stereospecificity of these reactions
Addition of HBr to allene (CH2=C=CH2) forms 2-bromoprop-1-ene rather than 3-bromoprop-1-ene, even though 3-bromoprop-1-ene is formed from an allylic carbocation. Considering the arrangement of orbitals in the allene reactant, explain this result.
Addition of HBr to allene (CH2 = C = CH2) forms 2-bromoprop-1-ene rather than 3-bromoprop-1-ene, even though 3-bromoprop-1-ene is formed from an allylic carbocation. Considering the arrangement of orbitals in the allene reactant, explain this result.
OChem HELP... Draw the conformational structures (chair or boat conformations) for the MAJOR product formed when 1-tert-butylcyclohexene reacts with each of the following reagents. Also, indicate if the product obtained is racemic form. a) Br2, CCl4 b) Br2, H2O c) OsO4, then aqueous NaHSO3 d) ICl e) mCPBA, then H3O+, H20 f) O3, then Me2S (conformational structure not required) g) BH3:THF, then H2O2, HO- h) D2, Pt i) Hg(OAc)2 in THF-H2O, then NaBH4, HO- j) BD3 :THF, then CH3CO2T
What is the major product formed when 3-methyl-1-butene is treated with Hg(C2H3O2)2 in a THF/ethanol mixture followed by NaBH4 in base?
Account for the regioselectivity and stereoselectivity observed when 1-methylcyclopentene is treated with reagent. Q) Br2 in H2O
cis-1-Bromo-4-tert-butylcyclohexane and trans-1-bromo-4-tert-butylcyclohexane both react with sodium ethoxide in ethanol to form 4-tert-butylcyclohexene. Explain why the cis isomer reacts much more rapidly than the trans isomer.