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- 5. Follow the curved arrows and write the products. + BF3 а. b.6. Which of the following structures represents trans-1,2-dimethylcyclohexane (circle correct answer)? CH3 .CH3 а. H;C. b. H3C CH3 CH ZCH3 с. CH3 d. H3C4.) Which molecule in each pair is more stable? Hint: consider the potential resonance contributors CH₂ 1+ a. CH₂CH₂CCH₂ or CH₂CH₂CH=CHCH₂ b. CH₂ CH=CH₂ or CH CH=CHCH₂ 0™ c. CH3CHCH=CH₂ or CH₂C=CHCH3 +NH₂ d. 0™ CH₂ or +OH NH₂ CH₂ NH₂
- ved D gg.com Predict the product (A) for the reaction below, then answer the questions below. OH H₂SO4 A i) Use a Frost's circle (polygon-and-circle) to construct orbital energy diagram for the product A ( assume product is a PLANAR molecule. (ii) Label the molecule as aromatic/ anti-aromatic/nonaromatic. (iii) Clearly draw the orbital energies diagram with the correct number of electron in each level. (iv) Label each energy level as bonding, antibonding or nonbonding.8 po Din 3. Consider 1-bromopropane. (looking at C₁ and C₂ bond) I) Draw a Newman projection (conformation) in which methyl and bromine are anti. II) Draw a Newman projection (conformation) in which methyl and bromine are in gauche. III) Draw a Newman projection (conformation) which represents the least stable eclipsed conformation.3) Draw the ECSF structures of (CH3)3CO (tert-butoxide ion) and CH30º (methoxide ion). Why is (tert-butoxide a PN but methoxide a GN even though both have a full O? (As it turns out, both are SBs) Redraw (CH3)3coe (ECSF) Why PN? Redraw CH30S (ECSF) Why GN?
- 2. For the following nucleophilic substitution reaction: NaOC(CH3)3 CH3 'CH3 CH3 a. Draw the first transition state (TS1), the reaction intermediate, and the second m transition state (TS2) in the labeled boxes. Make sure to show any formal charges, unfilled p-orbitals, and correct stereochemistry. TS₁ 41001 Intermediate ogmos TS2 amond- b. Which of three molecules you drew for part 'a' is lowest in energy? Write your answer in the box below. c. Draw the product(s) of the nucleophilic addition reaction shown. Make sure to use wedged and dashed lines to clearly show the resulting stereochemistry at each chiral center. If there is more than one possible product, draw one in each box - if not, leave one box blank. CH3 Br + NaOC(CH3)3Which group in each pair is assigned the higher priority in R,S nomenclature? а. — CDз, — СH b. - CH(CH3)2, - CH2OH c. - CH,CI, - CH,CH;CH,Br d. - CH,NH2, - NHCH,e. Rxn G :O: H3C-O H3COH NGỘI :O: ye Add a line to the energy diagram above for Rxn G.
- Rank the resonance structures in each group in order of increasing contribution to the resonance hybrid. Label the resonance structure that contributes the most as 3 and the resonance structure that contributes the least as 1. Label the intermediate contributor as 2. :O: a. CH3-C-ö-cCH, CH3-C-ö-CH3 CH,-C=0-CH, ÇH3 CH3-C-N=NH2 CH3 ÇH3Rank the following according to DECREASING reactivity towards SN2: CI I H™ CH3 OLE 2nd CH3 1st (most reactive) 3rd 4th (least reactive) H₂C CH₂ CH3 BIM [Choose ] [Choose ] [Choose] [Choose ] CI HECHT LAR HICH CH3 CUL1. For each compound, label the chemical equivalent hydrogens. Include cis-trans hydrogens on rings when they are inequivalent. Example: H₂C Br -CH₂ H₂C H₂C 8 CH₂CH₂ CH₂ CH₂