Devise a synthesis of (Z)-4,4-dimethyl-2-pentene using one of the starting materials and any of the reagents belowusing the fewest steps possible. If you need fewer than the 3 steps allowed, enter "none" for reagents in theremaining unused steps.Starting materialsÇH,HC=C-C-CH,HHC=C-C-CH,CH,HC=CHHC=C-CH,HC=C-CH,CH,HC=C-CH,CH,CH,CH,12346Reagentsa NANH, / NH, ()d iodoethaneg 1-bromo-3-methylbutaneį H2 / Lindlar catalystb N2OH/ H20e 1-bromopropaneh t-butyl bromidek H/ NH, ()c iodomethanef 2-bromopropanei H/ Pd on carbonI Na/ NH, ()Starting materialReagent for step 1Reagent for step 2Reagent for step 3

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Devise a synthesis of (Z)-4,4-dimethyl-2-pentene using one of the starting materials and any of the reagents below using the fewest steps possible. If you need fewer than the 3 steps allowed, enter "none" for reagents in the remaining unused steps. Starting materials ÇH, HC=C-C-CH, HCEC-C-CH, HC=CH HC=C-CH, HC=C-CH,CH, HC=C-CH,CH,CH,CH, 1 2 3 6 Reagents a NANH, / NH,0 d iodoethane g 1-bromo-3-methylbutane į H/ Lindlar catalyst b NaOH/ H,0 e 1-bromopropane h t-butyl bromide k H/ NH, () c iodomethane f 2-bromopropane i H,/ Pd on carbon I Na / NH,() Starting material Reagent for step 1 Reagent for step 2 Reagent for step 3

Devise a synthesis of (Z)-4,4-dimethyl-2-pentene using one of the starting materials and any of the reagents below using the fewest steps possible. If you need fewer than the 3 steps allowed, enter "none" for reagents in the remaining unused steps. Starting materials ÇH, HC=C-C-CH, HCEC-C-CH, HC=CH HC=C-CH, HC=C-CH,CH, HC=C-CH,CH,CH,CH, 1 2 3 6 Reagents a NANH, / NH,0 d iodoethane g 1-bromo-3-methylbutane į H/ Lindlar catalyst b NaOH/ H,0 e 1-bromopropane h t-butyl bromide k H/ NH, () c iodomethane f 2-bromopropane i H,/ Pd on carbon I Na / NH,() Starting material Reagent for step 1 Reagent for step 2 Reagent for step 3

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...

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