8. When (1R,2R)-2-bromocyclohexanol is treated with NaOH, the product does not exhibit a broad IR stretch at 3000-3500 cm³¹ and does not rotate plane polarized light. However, when (1R,2S)-2-bromocyclohexanol is treated with NaOH, the product exhibits a strong, broad IR signal at 3000-3500 cm³¹, and is found to be optically active. Draw the two starting materials and propose a mechanism for their reactions with NaOH that is consistent with these observations. (16 pts)

How many stereoisomers are possible for this cyclic hemiacetal?

Identify the unknown compound from its IR and proton NMR spectra. C4H6O: 'H NMR: 82.43 (1H, t, J = 2 Hz); 8 3.41 (3H, s); 8 4.10 (2H, d, J = 2 Hz) IR: 2125, 3300 cm¹ The C4H6O compound liberates a gas when treated with C2H5 MgBr. Draw the unknown compound. Select Draw с H Templates More

How many 1H NMR signals does each alkene exhibit?

Identify products A and B from the given 1H NMR data. Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1H) ppm. What is the structure of B?

An unknown compound C of molecular formula C6H12O32 exhibits a strong absorption in its IR spectrum at 1718 cm−1 and the given 1H NMR spectrum. What is the structure of 1H NMR spectrum. What is the structure of C?

An unknown compound C of molecular formula C6H12O3 exhibits a strong absorption in its IR spectrum at 1718 cm−1 and the given 1H NMR spectrum. What is the structure of C?

Propose a structure for a C,H150,N compound that is unstable in aqueous acid and has the given NMR spectra. 'H NMR: 8 2.30 (6H, s); 8 2.45 (2H, d, J = 6 Hz); 8 3.27 (6H, s); 8 4.50 (1H, t, J = 6 Hz) 13C NMR: 8 46.3, 8 53.2, 8 68.8, 8 102.4 Draw C,H1502N. Select Draw Rings More C N APR étv N Aa MacBook Air

4. The 1H NMR spectrum shown below corresponds to one of the molecules A-D. Identify the molecule and then provide the complete IUPAC name for the molecule. Don't forget about stereochemistry. он ÕH ÕH B D 11 10 8 6 5 1 'H NMR: 3.35 (1H, m), 1.66 (1H, m), 1.36 (9H, m, overlapping signals), 0.91 (6H, d), 0.90 (3H, t)

When compound A (C5H12O) is treated with HBr, it forms compound B (C5H11Br). The 1H NMR spectrum of compound A has a 1H singlet, a 3Hdoublet, a 6H doublet, and two 1H multiplets. The 1H NMR spectrum of compound B has a 6H singlet, a 3H triplet, and a 2H quartet. Identifycompounds A and B.