A b 4 nmr isomer puzzles a isomer of composition c 7

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A B 4. NMR Isomer puzzles. a. Isomer of composition C 7 H 12 with 2 1 H and 5 13 C NMR resonances. b. Isomer of composition C 8 H 8 with a single 1 H and 13 C NMR resonance. c. Compound of C 7 H 12 with 4 1 H (2:2:4:4 ratio) and 3 13 C NMR resonances. Chem 33, Kanan & Stack, 2012, PS 9; pg 2
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6. Treatment of 4-penten-1-ol with aqueous Br 2 yields a cyclic bromoether compound shown below rather than 5-bromopentane-1,4-diol. Suggest a mechanism using curved arrows to account for this product. HO Br 2 H 2 O O Br 2-(bromomethyl)tetrahydrofuran pent-4-en-1-ol 5. Consider the configurational stereoisomers that result from the following reactions. a. Epoxidation ( m -CPBA) and bromination (Br 2 ) of trans -2-butene. H 3 C CH 3 Br 2 m-CPBA H 3 C Br 2 m-CPBA H 3 C c. Explain why bromination of c is- 2-butene gives configurational enantiomers similar to the epoxidation of t rans- 2-butene. b. Epoxidation ( m -CPBA) and bromination (Br 2 ) of cis -2-butene. Chem 33, Kanan & Stack, 2012, PS 9; pg 3
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CH 3 HBr I 2 , H 2 O ICl, Et 2 O Br 2 , Et 2 O BD 3 , THF H 2 O 2 , NaOH dilute H 2 SO 4 OsO 4 NMO NMO = N O O THF = O m -CPBA = Cl O O O H H 3 C 7. Complete the following wheel of alkene reactivity.
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