A molecule of the molecular formula C5H11Br gives rise to the NMR spectrum below. When reacted with NaOH and water, it forms a product which by NMR has 2 protons 1H at 5.4 ppm and 1H at 5.5 ppm each having a 3J coupling of 17 Hz. (other protons also present) The product also has an IR stretch at 1550 cm 1. Provide the structures of the starting material (1 pt) and product (2 pts) NaOH H20 C,H„Br 6H triplet 4H quintet 1H quintet pom

10.9 A compound of molecular formula C₂H₂ClO₂ has peaks at 55.8, 56.8, 112.9, 113.4, 116.2, 123.1, 149.5, and 153.9 in its proton- decoupled ¹3C NMR spectrum. Give the structure of the compound and assign as many signals as possible to the carbons in the structure.

A student takes an IR spectrum of an unknown compound. The IR spectrum shows significant stretches at 3159 cm³¹ (m, sh), 3089 cm ¹ (m, sh), 3000 cm ¹ (m, sh), 2997 cm-¹ (m, sh), 1620 cm-¹ (s, sh), 1494 cm-¹ (s, sh), and 1210 cm-¹ (s, sh). Which possible compound is it? Key: S = Strong, M = Medium, W = Weak, Sh = Sharp, Br = Broad Anisole Aniline O Acetanilide O Acetone O Phenol

The mass spectrum of 2,2-dimethylpropane shows only a very weak molecular ion peak at m/z = 72. However, a large peak at m/z = 57 is seen. Suggest a possible structure of the fragment giving rise to this large peak and suggest a reason as to why this peak is so large.