How many more gauche interactions are there in axial trans-1,2-dimethylcyclohexane than in the equatorial form? This is not quite as trivial as it seems!
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- Draw a resonance structure, complete with all formal charges and lone (unshared) electron pairs, that shows the resonance interaction of the acetoxy with the para position in phenyl acetate. phenyl acetate ● CH3 • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. In cases where there is more than one answer, just draw one. Sn [F ?2. Our knowledge of chair conformations allows us to use them to determine a great deal about a reaction's mechanism. In particular, using a t-butyl group to 'fix' a cyclohexane in a single conformation can help us learn about the spatial requirements and energetics of a reaction. Consider the following two reaction products: CN 1) NaCN 2) H+ OH 1) NaBH4 2) H3O+ OH Group -H -CN A Value (kcal/mol) Defined as 0 0.2 kcal/mol -OH 1.0 kcal/mol c. For any products that do have the most stable conformation, does our understanding of the mechanism allow for ‘thermodynamic control'? d. If one of the products is not the most stable, can you explain the observed product based on ‘kinetic control'? (Does the most easily formed transition state result in the observed product?) Consider the chair-like conformation of the starting material.2. Our knowledge of chair conformations allows us to use them to determine a great deal about a reaction's mechanism. In particular, using a t-butyl group to 'fix' a cyclohexane in a single conformation can help us learn about the spatial requirements and energetics of a reaction. Consider the following two reaction products: a. NO NID ALOH 1) NaCN 2) H+ 1) NaBH4 2) H3O+ OH Group -H -CN -OH A Value (kcal/mol) Defined as 0 0.2 kcal/mol 1.0 kcal/mol Draw the most stable chair conformation for each of the two products. b. Based on the A values in the table above, do the two products have the most stable conformation at the new stereocenter?
- Rank the following cyclohexane isomers in order of stability (where the Most Stable Isomer = 1). If you believe multiple isomers have the same approximate overall energies indicate this by ranking them with the same number. Me. Me Me.* Me Me Me Me Me Ме,. Me Me* Me Ме, Me Me MeDraw the structure of the alkene with the molecular formula CH10 that reacts with Br, to give this compound. CH3 Br Br • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. opyste ot pt pt pt ptExplain the fact that the C-O stretch in ethers and esters occurs at 1000-1100 cm-1 when the C is sp hybridized, but at 1250 cm- when it is sp2 hybridized.
- Identify the most stable, second most stable, and least stable conformation resulting from rotation about the bond indicated by the purple arrow. Assume, in this context, that the methoxy group is sterically smaller than the methyl group, an assumption that is supported by the fact that methoxy groups induce less axial strain than methyl groups in cyclohexane conformations. H H CH₂ CH₂ QOCH, HIC DOCH, HIC H₂C H₂C A Most stable Second most stable OCH₂ Least stable HH с H₂ OCH H₂C [Choose] [Choose] [Choose ] OCH₂ CH₂ D H₂C+ HH носна H₂C H₂C H H H OCH₂Which of these products is the result of a hydride shift occuring during the substitution reaction of aqueous 2-chloro-3-methylpentane? CH3CH2CCH2CH3 || CH2 CH3CH(OH)CH(CH3)CH2CH3 CH2=CHC(CH3)=CHCH3 CH3CH=C(CH3)CH2CH3 CH3CH2C(CH3)CH2CH3 | OHThe thermal ring opening of trans-3,4-dimethylcyclobutene may yield two isomers, but only one isomer forms. Why? * CH3 CH3 H. heat ...C CH3 CH3 (2E,4E)-hexadiene H CH3 CH3 heat .CH3 CH3 H
- Shown below is a carbocation intermediate in an electrophilic addition reaction of HCl with an alkene. For the conformation shown, select each hydrogen whose bond to carbon is aligned for effective hyperconjugation with the vacant p orbital on the positively charged carbon. Each adjacent carbon will have only one C-H bond so aligned. • Gray = C; white = H; red = 0; blue = N; dark green = Cl; brown =Br; light green =F; purple = I; yellow = S; orange = P. • Double click to select atoms. • You can zoom in and out using the mouse scroll wheel (or pinch to zoom on touch screens).An alkene having the molecular formula C7H₁4 is treated sequentially with ozone (03) and zinc/acetic acid to give the product/s shown. H3CO || CH3CHCH + H3C Draw a structural formula for the alkene. *8 CH3 • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. On [] ? Ⓡ ChemDoodleⓇ3. Two substitution products result from the reaction of 3-chloro-3-methyl-1-butene with sodium acetate (CH:CO2 Na*) in acetic acid under SN1 conditions. Identify the products. (Hint: Resonance form) Please predict the products in the following reactions. (Hint: Stereochemistry!!) CH,CH3 SN2 conditions + НО- CH3 Br (S)-2-bromobutane CH,CH3 SN1 conditions + H,O CH3 Br (S)-2-bromobutane 4.