b) t-Pentyl Chloride Exp: ОН CI HCI

Consider the product below a) Would this product show a signal in a UV-Vis spectrum? Why? b) Would this molecule have a non-zero alpha-value in polarimetry? Why? c) What stretches would be expected in an IR spectrum of this molecule? d) Predict the 1H NMR spectrum for this molecule. For H1 to H6 e) Predict the 13C NMR spectrum and DEPT spectra for Carbon A- Carbon G. Use (+) for positive signals, (-) for negative signals, and (X) for no signal in the DEPT NMR spectra. f) If a base such as NaOH was used, it would be harder to determine the major product before running the reaction. Once the reaction was run, how would you determine the product favored using spectroscopy?

A student attempted to create the following conjugated compound via a double elimination. The mass spectrum showed the correct compound had been formed. And yet, the IR spectrum should definitive evidence that the wrong compound was formed. Answer using the bold letters. What do you think was formed ? Which functional group? A alcohols B alkyne C ketone D another functional group What peak was lacking from the IR spectrum that should have been there E 1500-1800cm1 F 2000-2500cm-1 G 3000-3500cm1 What peak was present in the IR spectrum that confirmed the wrong product H 1500-1800cm1 I 2000-2500cm1 J 3000-3500cm1 Br 2eq NaOH

Match the four structures with the four IR spectra (by putting a proper letter in the box to the right of each spectrum). Use specific IR absorptions for various functional groups to identify the structures. Circle the important peaks in each spectrum that helped you identify the functional group(s) and label the functional group beside it.

c. Can the carboxylic acid derivative shown as a reactant in part a be used  make an anhydride? d. Can product A be used to make a carboxylic acid? e. What type of carboxylic acid derivative iss product A? f. Using IR spectroscopy, how would you determine the reaction in part a produced A? (Compare the expected IR spectra for the reactant and product structures to provide the best answer. Be specific.)

24. How can IR spectroscopy help to monitor the following reaction? OH e PCC a. What structural features distinguish the reactant from the product? b. What structural features would NOT help in distinguishing the two structures? C. What would you look for in the IR data of both structures? d. How would you know when the reaction was complete?

2. READ THE DIRECTIONS TO EACH QUESTION CAREFULLY - not following the directions means you get the question wrong! 3. FORMAT YOUR ANSWERS AS DIRECTED-formatting your answers incorrect means you get the question wrong! 4. Below are the IR regions and NMR chemical shifts table for use with the spectroscopy problems: ¹H NMR 12 11 10 R C=O ... OH R 'H 9 8 7 H ppm 6 OH C=C-H 5 NH H-C-X H-C-O -OH -NH X = F, Cl, Br (i.e. electronegative atom) 3 2 H-C-N H-C-S -CH3 -CH₂- C=C-H H-C-C=O -CH H-C-C=C HC-0 0 4000 DIO small range range of values broad peak =C-H N-H 3250- 3300 broad with spikes -3300 3500 -O-H broad-3300 -3400 O-H -CN usually strong N-H CO =C H H 2730- 2820 3000- 2 peaks 3100 1 H -C-H 2850- 2960 O 0 -C-O-H broad-3000 3000 -CEN 2200 -CICH ← 2200 2500 wavenumber, cm-1 2000 C H.C. N н 1680 0.00 0.00 0.00 H 1600- 1660 O C. OR 2 :ں 1600 1500 1000

symmetrical bonds do not appear in IR spectra (or the signal is unusually weak). Given that general finding, which signal appears to be “missing” in the IR spectrum of maleic anhydride? At approximately what wavenumber would you expect to find it?