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1 Problem 1 Using the chemical shift rules for CH-, CH 2 - und CH 3 -Groups draw the stick spectrum for propionic acid chloride. There is no shift rule for acid chloride groups. Search for an acceptable alternative.
2 Problem 2 C 4H 8O Exercises, problem 2: Determine the structure. Note that the integrals have been shifted a few millimeteres to the left for clarity.
3 Problem C 3H 9N Exercises, problem 3: Determine the structure! Explain the splitting patterns! How large do the coupling constants have to be? Estimate the chemical shifts using the appropriate shift rules!
4 Problem 4 Hz C 3 H 7 NO 2 ( 1 H; 300 MHz) Exercises, problem 4: Determine the structure. Why is a clean sextet observed at 2? What is the actual multiplicity? The data are from a collection of the Pacific Lutheran University, Washington.
5 Problem Exercises, problem 5: During the photo-chlorination of toluene, a mixture of products is obtained. Using the proton spectrum, determine the two components! In what mole ratio are the present?
6 Problem 6 C 4 H 10 O 2 Integral Exercises, problem 6: Determine the structure. Note that the integrals have been shifted a few millimeteres to the left for clarity.
7 Problem 7 C 6H 12O 2 6x Exercises, problem 7: Determine the structure. Check the chemical shifts using shift rules!
8 Problem 8 C 6 H 6 N 2 O C 6 H 6 N 2 O C 6 H 6 N 2 O Exercises, problem 8: Distinguish the three isomers of a disubstituted benzene derivative! Also interpret the chemical shift of the broad Signal! Which solvent was used?
9 Integral ,QWURGXFWLRQ ([HUFLVH Problem 9 C 9 H 9 OCl 4x Exercises, problem 9: Determine the structural formula using the NMR-spectrum and the molecular formula!
10 Problem 10 4x C 7 H 7 OCl Exercises, problem 10: Determine the structure!
11 Problem C 9H 7NO H z Exercises, problem 11: Determine the structure and the conformation!
12 Problem 12 Hz C 5 H 10 O ( 13 C{ 1 H}; 62.9 MHz) Exercises, problem 12 (page 1): Determine the structure of the two structural isomers (see additional spectra on second page)!
13 Hz C 5 H 10 O ( 13 C{ 1 H}; 62.9 MHz) Exercises, problem 12 (page 2): Assign all of the signals in the spectra on this page!
14 Problem ( 1 H; 60 MHz; simuliert nach) Originaldaten) Exercises, problem 13: The 6 spectra correlate with the following structural formulae: CH 3 -CH 2 -OH, Cl 2 CH-CH 2 -CHCl 2, (CH 3 ) 2 -CH-CN, CHCl 2 -CHCl-CHCl 2, CHCl 2 - CHO, N C-CH 2 -CH 2 -Cl, CHCl 2 -CHCl 2, CH 3 -CH 2 -Cl, CH 2 Br-CH 2 -CH 2 Br, CH 3 - CH 2 Br, CH 3 -CHCl 2 und (CH 3 ) 2 -CHCl. Assign them correctly and explain your choice!
15 Problem 14 C 6 H 14 O Exercises, problem 14: Determine the structure. Hint: Work out the multiplicity of the multiplets at about 3.6! How can this be explained?
16 Problem 15 C 8H 10O x 2 Exercises, problem 15: Determine the structure!
17 Problem C 8H 7ClO Exercises, problem 16: Determine the structure! Can you distinguish reliably between the two alternative structures?
18 Integral ,QWURGXFWLRQ ([HUFLVH Problem 17 C 9 H 10 O 3 4x Exercises, problem 17: Determine the structure!
19 Problem 18 C 12 H 14 O 4 4x C 12 H 14 O 4 4x Integral Exercises, problem 18: Determine the structures of the two isomers! Compare the spectra! (solvent: CDCl 3 )
20 Problem 19 C 6 H 14 O 2x Exercises, problem 19: Work out the structure!
21 Problem C 3 H 5 Br Exercises, problem 20 (page 1): Determine the structure! Determine and explain all coupling constants! Use only the 250 MHz-Spectrum!
22 C 3 H 5 Br ( 1 H; MHz) Exercises, problem 20 (page 2): The compound is the same as on page 1. Note the effect of the different measuring frequency on the shape of the multiplet!
23 Problem 21 7UDQVODWHG IURP $ODQ.HQZULJKW C 7 H 8 O 4x Exercises, problem 21: Determine the structure. Hint: You need to consider some unlikely (impossible?) structures!
24 Problem Hz Hz C x H y O z ( 1 H; 300 MHz) 10x C x H y O z ( 13 C{ 1 H}; 75 MHz) Exercises, problem 22: Determine the Structure of the molcule! Which solvent was used? (The FIDs and the spectra are from a data collection at the Widener University, Chester)
25 Problem H z C 3H 3N Exercises, problem 23: Determine the structure! Make correct stereo chemical assignments for all protons! Determine the magnitude of all coupling constants!
26 Problem 24 C 6 H 7 N C 6 H 5 NO Exercises, problem 24: Which two singly substituted benzene derivatives are present? Estimate the chemical shifts using shift rules! Take note of (but do not interpret) the complicated splitting pattern!
27 Problem A C 8H 9ClO 4x A B 4.5 C B 4.0 C 3.5 Exercises, problem 25: Determine the structure! Assign all proton signals! Use shift rules and the expanded region! Corresponding multiplets are marked with the same letters in the main spectrum and the expanded regions.
28 Problem C 8H Exercises, problem 26: Determine the structure!
29 Problem 27 C 5 H 9 NO 4 4x Exercises, problem 27: Using the 1 H-NMR spectrum and the empirical formula determine the structure of the compound! Note: - The method of synthesis precludes the formation of a peroxide. - The compound is colourless.
30 Problem 28? 4x 7 C 9H 10O ? Exercises, problem 28: Which compound is shown here? Which acid-free solvent was used?
31 Problem C 8H 9BrO Exercises, problem 29: Determine the structure! Which solvent was used?
32 Hz ,QWURGXFWLRQ ([HUFLVH Problem 30 C 8 H 10 O Exercises, problem 30: Determine the structure. Hint: Start by considering from which group the signal at about 1.9 arises.
(b) How many hydrogen atoms are in the molecular formula of compound A? [Consider the 1 H NMR]
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