Chapter 12 IR Bonus Homework Answers

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Chapter 12- Infrared Spectroscopy 1. Match the IR spectra with the appropriate chemical structure from the list below. Show work to explain your answer. 2. Match the IR spectra with the appropriate chemical structure from the list below. Show work to explain your answer. ~ 01 X X & / · If Stretch No strong -1 peak ~100 so no c = 0 Indicates No Alkene Either x0x X C - H v0 K shows Sharp A1kc42 =C - H stretch strong 100 Peak - - so c 0
3. Match the IR spectra with the appropriate chemical structure from the list below. Show work to explain your answer. 4. Match the IR spectra with the appropriate chemical structure from the list below. Show work to explain your answer. x x x x s shows =c H strong for Bonding x x x X o H stretch slight * Peak inficates Alkene c = c
5. Match the IR spectra with the appropriate chemical structure from the list below. Show work to explain your answer. 6. Match the IR spectra with the appropriate chemical structure from the list below. Show work to explain your answer. X o + X - Indicate g No c = 0 or 0 - H c = c stretch with stions Alkene xX0 + + f - N n No strong PaKat 1700Ch-4 so no i 0 strong Peak a + less than DCO sussests Alkeve
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7. Match the IR spectra with the appropriate chemical structure from the list below. Show work to explain your answer. 8. Match the IR spectra with the appropriate chemical structure from the list below. Show work to explain your answer. 0 f yXX I No Bants at 1600 so no Benzene saturated C - H strong band stratch a t = 1700 - inficates C = 0 2xxX0X R No strong peak ~1700 0 - H so no stretch * c = 0 Alcohol
9. Match the IR spectra with the appropriate chemical structure from the list below. Show work to explain your answer. 10. Spectra are given for three compounds. Each compound has one or more of the following functional groups: alcohol, amine, ketone, aldehyde, and carboxylic acid. Determine the functional group(s) in each compound and assign the major peaks above 1600 cm-1. xxx0 2 - H stretch saturated & c = 0 stretch H A - H stretch & C - H stretch Secondary Amine 2 H c = c stretch stretch Alkehe
11. Predict the characteristic infrared absorptions of the functional groups in the following molecules. (a) cyclohexene (b) pentan-2-ol (c) pentan-2-one (d) pent-1-yne 12. Which of the following circled bonds gives the weakest peak in the infrared spectrum for a stretching vibration? H 1 2 3 4 * o 1t stretch Carboxcyllic Aci 112 - H stretch c = 0 -> stretch o -H 11 stretch Saturated C 1 H stretch Alcohol 1 * (C C)(1650(n- 1) (( - H) (3000-3200cm t) I · H (0 H) (2800 3000(n 1) (C -H) (2800 - 3000ch -1) M ( = 0)(1710 1730(n 1) ( - H) (2800 3000 (n- ) M * (C = C (2200(n - 1) (C-H)(2800 - 3000(n-1) O I would give the weakest peak as it is an internal alkene showing no polarity.
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13. Using IR, how could you tell if the reaction below was complete? 14. How could IR spectroscopy be used to distinguish between the following pair of compounds? CH 3 COCH=CHCH 2 CH 3 and CH 3 COCH 2 CH 2 CH=CH 2 15. Deduce a possible structure for the compound with the IR absorptions below. C 5 H 8 O: 2950, 1750 cm -1 to determine if this reaction is complete we can compare the two resulting IR spectra and look for a sharp peak around 100cn-t and a broat peak From 3000cm-1. This would tell us if the Carsoxcyllic acid was formet. Of the alkene boats shown in the figure On is internal and the other is terminal. The terminal bond will show a stronger peak relative to the internal Allene bond. 2 4 + c 0 stretch & Ketone 1)