2009chem14c(midterm2) - C h e m is t r y 1 4 C W in t e r 2...

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Chemistry 14C Winter 2009 Exam 2 Page 1 For any question on this exam worth three or more points, you have two choices: answer the question as written or you may write and circle the phrase “one point”. If you write “one point” you will receive one point (and only one point) of credit for the question. “One point” overrides anything you have written for that question, regardless of its accuracy. Example: (10) Briefly explain everything about organic chemistry. A style of pottery found at a Pueblo site in New Mexico suggested that the Native American habitants might have consumed chocolate-like beverages during rituals. To test this theory, the organic residues were extracted from the pottery shards, and the residues subjected to spectroscopic analysis. In questions 1–8 we explore this study. Questions 1 and 2 refer to ethyl acetate, the solvent used to extract the organic residues from the pottery shards. The solvent was removed before spectroscopic analysis of the residue, but solvent traces may remain and interfere with interpretation of the spectra. Therefore we need to predict the spectra of the solvent so we know which spectral peaks should be ignored. Ethyl acetate 1. (4) Write the stretching frequencies (or ranges) and corresponding bonds of two peaks in the infrared spectrum of ethyl acetate. Example: Bond: Fe–O Stretching frequency: 4000-500 cm -1 Bond: ___________ Bond: ___________ Stretching frequency _____________ cm -1 Stretching frequency _____________ cm -1 2. (12) Write the splitting patterns and approximate chemical shifts of three signals in the proton NMR spectrum of ethyl acetate. Example: Chemical shift: 14–16 ppm Splitting pattern: Triplet
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