Draw a structure consistent with the following set of data: a hydrocarbon with a molecular ion at m/z = 68 and IR absorptions at 3310, 3000−2850, and 2120cm−1.

Do not give handwriting solution.

Use the 1H NMR and IR spectra given below to identify the structure of compound B (molecular formula C4H8O2).

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 J coupling of 17 Hz. (other protons also present) The product also has an IR stretch at 1550 cm1. Provide the structures of the starting material (1 pt) and product (2 pts) NaOH H20 C5H1,Br 6H triplet 4H quintet 1H quintet 10 8 7 6. 4 3 1 HSP-06-347 ppm

Cyclohex-2-enone has two protons on its carbon–carbon double bond (labeled Ha and Hb) and two protons on the carbon adjacent to the double bond (labeled Hc). (a) If Jab = 11 Hz and Jbc = 4 Hz, sketch the splitting pattern observed for each proton on the sp2 hybridized carbons. (b) Despite the fact that Ha is located adjacent to an electron-withdrawing C = O, its absorption occurs upfield from the signal due to Hb (6.0 vs. 7.0 ppm). Offer an explanation.

A compound displays a sharp doublet at 3400 cm-1 in its IR spectrum. The mass spectrum has a molecular ion with m/z = 115 and a base peak of m/z=72. Draw a structure that best fits this data.

Draw a structure for a compound that meets the following criteria: C7H8 with IR absorptions at 1600 and 1500 cm^-1 and at 3030 cm^-1.