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It is sometimes necessary to isomerize a cis
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- As a rule, axial alcohols oxidize somewhat faster than equatorial alcohols. Which would you expect to oxidize faster, cis-4-tert-butylcyclo-hexanol or trans-4-tert-butylcyclohexanol? Draw the more stable chair conformation of each molecule.arrow_forwardAnother important pattern in organic synthesis is the construction of CC bonds. Using your reaction roadmap as a guide, show how to convert propane into hex-1-en-4-yne. You must use propane as the source of all of the carbon atoms in the hex-1-en-4-yne product. Show all reagents needed and all molecules synthesized along the way.arrow_forwardDraw the structure for an alkene that gives the following reaction product. 1. Hg(OАc)2, Н2О ? -CHCH3 2. NABH4 ОН Ignore alkene stereochemistry. You do not have to explicitly draw H atoms. In cases where there is more than one answer, just draw one. Visited opy aste ChemDoodlearrow_forward
- 3. Provide the mechanism going from a cyclohexenone to an a,ß-unsaturated carbonyl and a ketone. + H-OH RO, ROH, Aarrow_forwardDraw the product formed from cyclohex-2-enone in each of three reactions. Reaction 1 Reaction 2 Reaction 1 1. NaCN 1. (CH3)2CuLi Reaction 2 product product 2. H3O*, H20 2. CH3CH21 A 1. EtO,CCH,CO¿Et NaOEt, HOET 2. Hао", Н-0, д Reaction 3 Reaction 3 productarrow_forwardWhich represents an efficient synthetic route to go from an alkane to an alkene? O elimination with NaNH2, followed by a water workup O anti-Markovnikov hydrohalogenation, followed by elimination O radical bromination, followed by elimination O hydration, followed by elimination O hydration, followed by ozonolysis of the double bondarrow_forward
- 4. Give the starting alkene and any other reagents needed to selectively make the following compounds (with no organic byproducts!): OH L Eto OH all OH Br Br Brarrow_forwardTreatment of alkenes A and B with HBr gives the same alkyl halide C. Draw a mechanism for each reaction, including all reasonable resonance structures for any intermediate. Br -CHCH2CH, HBr HBr -CH=CHCH, -CH2CH=CH2 A B.arrow_forwardWhat reagent/reagents is/are necessary to transform the starting molecule into the desired product? SO3H ?arrow_forward
- 35) Draw the major product of the following reaction: 1. R₂BH 2. H₂O₂, OH -C=C-Harrow_forwardDraw the product formed from cyclohex-2-enone in each of three reactions. Reaction 1 Reaction 2 Reaction 1 1. NaCN 1. (CH3)2CULI Reaction 2 product product 2. H30*, H2O 2. CH3CH2I 1. EtO,CCH2CO½ET NaOEt, HOET 2. Hао", Н-о, д Reaction 3 Reaction 3 productarrow_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_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning