Worksheet 2

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University of California, Santa Barbara *

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6AL

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Chemistry

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Dec 6, 2023

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Chem 6AL Fall 2023 In class Worksheet 2 Your Name: ____________________________________ 1. What is the mole fraction of ethyl acetate in the vapor phase above a liquid solution that is a mixture of 5mL ethyl acetate and 5mL of hexane? (ethyl acetate: density = 0.902 g/mL, 88.11 g/mol; hexane: 0.661 g/ml, 86.18 g/mol). 2. What is an azeotrope? How can you use a temperature composition diagram to determine if two liquids form an azeotrope? 3. How would your results from Experiment 2 have been different if water and ethanol did not form an azeotrope? 4. How can you distinguish methylamine, dimethylamine, and trimethylamine using IR spectroscopy? 5. IR absorption bands: Use the Bruice textbook, lab notebook, or an online resource to find approximately where the following bond stretches appear in an IR spectrum. Note any important characteristics. a. O-H alcohol _____________ cm -1 b. O-H carboxylic acid _____________ cm -1 c. N-H _____________ cm -1 d. sp C-H _____________ cm -1 e. sp 2 C-H (alkene) _____________ cm -1 f. sp 2 C-H (aldehyde) _____________ cm -1 g. sp 3 C-H _____________ cm -1 h. C≡C _____________ cm -1 i. C=O _____________ cm -1 j. C=C _____________ cm -1 k. C-O _____________ cm -1

6. Use your answers in question 10 to predict the IR spectrum of the following molecules. Note: these will not be super accurat e sketches, but we are just looking to recognize where the functional groups appear. We don’t need to worry too much about the fingerprint region (other than C-O absorption bands). a. 2-butanone b. N,N-diethylamine c. hexanoic acid d. pent-4-en-2-ol e. 1-butanamine 7. Sketch IR spectra for the following pairs of compounds (each pair on the same spectra). 2-hexyne and 1-hexyne 4-hydroxy-2-butanone and butanoic acid

Chem 6AL In class Worksheet 2 8. Which molecule produces the IR spectrum below? Justify your reasoning. 9. Propose the structure of the organic compound with molecular formula of C 3 H 6 O 2 that produces the following IR spectrum. Annotate the spectra by indicating which bonds in your molecule are responsible for the absorption bands in the IR spectrum. 10. The following spectra is for an unknown compound. Propose a structure for the compound (Hint: the molecular formula is C 5 H 11 N). Annotate the spectrum, showing which bonds in your molecule produce with absorption bands in the IR spectrum. The labeled tick marks on the x-axis are (from left to right) 4000, 3000, 2000, 1500, 1000, and 500 cm -1 . 3000 2000 1500

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