Compounds n and o what are the structures of these

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Compounds N and O ). What are the structures of these two anti-Markovnikov diastereomers (note that some experimental data are given about each one of them). Compound N (a) C 4 H 8 O 2 (b) 1 H-NMR: 2 signals (3:1 ratio) (c) 13 C-NMR: 2 signals (d) dipole moment: zero Compound O (a) C 4 H 8 O 2 (b) 1 H-NMR: 2 signals (3:1 ratio) (c) 13 C-NMR: 2 signals (d) dipole moment: non-zero 3 12 2 2 O CH 3 H H HSO 4 H B C C H O CH 3 H C C H O CH 3 H res form OK, not required O H CH 3 C C H H O O CH 3 CH 3 H B mech = 2 intermediate = 3 intermediate = 3 mech = 2 mech = 2 no partial bisulfate OK, not required C C H 3 CO H H OCH 3 C C H 3 CO H H OCH 3 if methoxide (CH 3 O ) is used to capture carbocation, 5/12 pts note: HB/B - can only be used for actual acid/base reactions no partial no partial
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Name _______________________ Page 5 F.05.210E2 V. (25 points) A. The molecule shown here ( Compound P ) is an intermediate in the synthesis of cytoxazone A, a cytokine inhibitor. (a) Draw the three Newman projections for the staggered conformations for the analysis of the C 3 -C 4 bond rotation (use C 3 as the front atom and C 4 as the back atom). H H 3 CO H OCH 3 H 3 CO Compound P 3 4 Conformation P 1 Conformation P 2 Conformation P 3 Rank the relative stabilities of these 3 conformations, by placing the labels P 1 , P 2 , and P 3 in the proper order (note: the structures above need to reflect the three different staggered forms for the specified bond in order to receive credit for this part of the problem). (b) most stable: intermediate stability: least stable: B. The "but" in "butane" is derived from the word butter, because one of the major components of rancid butter is a 4-carbon acid that was called butanoic acid. HO C O CH 2 CH 2 CH 3 butanoic acid Given that the name "butanoic acid" reveals the suffix for that functional group, provide the complete name (including stereochemical designation) for this molecule: HO O Br H C. Draw the structure for the molecule with this name: 1,1,2,2-tetrachloro-4,4-dimethylcyclopentane 4 4 4 3 6 4 H 3 CO H OCH 3 H OCH 3 H OCH 3 H H OCH 3 OCH 3 H OCH 3 H 3 CO OCH 3 P 1 P 2 P 3 ( R )-2-bromo-6,6-dimethylheptanoic acid Cl Cl Cl Cl CH 3 CH 3 -2 per type of error: stereochem, punctuation, prefix spelling, root name, suffix no partial (1) C 4 in front -3 (2) wrong connectivity -3 (3) wrong stereochem -3
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