CHEMISTRY 251 Spectroscopy Problems

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1 EMISTRY 251 Spectroscopy Problems The IR below is most likely of a: aldehyde alkane alkene alkyl bromide alkyne

2 The IR below is most likely of a: acyl chloride alcohol 3 amide ether nitrile

3 The IR spectrum below is most likely of: N

4 The IR spectrum below is most likely of: N 2 N Et N

5 The IR below is most likely of a: N 2 N N 2 2 N N 2 N

6 The IR below is most likely of a: N 2 N N 2 2 N N 2 N

7 The IR below is most likely of a: N

8 The IR spectrum below is most likely of: ( 2 ) ( 2 ) ( 2 )

9 The IR spectrum below is most likely of: N N

10 The mass spectrum below is most likely of: Note: The atomic mass of is 12, the atomic mass of is 1, the atomic mass of N is 14, & the atomic mass of is 16. Br exists as ~50% 79 Br and 50% 81 Br. l exists as ~75% 35 l and 25% 37 l. acyl bromide alkyl chloride alcohol amine ether

11 The mass spectrum below is most likely of: alkyl bromide acyl chloride alcohol amine ether

12 The mass spectrum below is most likely of: alkyl bromide acyl chloride alcohol amine ether

13 The mass spectrum below is most likely of: l N

14 The mass spectrum below is most likely of: l Br N 3 3 2

15 Earlier, you learned that alkynes could be converted to alkanes via hydrogenation (Scheme 1). Were you to run such a reaction in the lab, how could you use IR to determine when the reaction was done? Scheme Pt/ Take IR spectra of the reaction at regular time points. In this way monitor the disappearance of the alkyne stretch at cm -1. When it's gone the reaction is done.

16 (a) Describe how one would use IR to distinguish between the two amine isomers shown below N 2 3 A B N The IR spectrum of B will have an stretch at cm -1. That region will be clear of any peaks for A. (b) Describe how one would use mass spec to distinguish between the two amine isomers shown below (5 pts) N 2 3 A B N N [M 15]!-cleavage N N A parent peakd for both A & B m/z 101 B!-cleavage 1!-cleavage N N 3 [M 29] [M 43]

17 A. List in tabular form the expected signals for the proton NMR spectrum of E and then sketch that spectrum. 3 l 3 E proton(s) relative chemical shift (ppm) multiplicity integration l ~3.8 ppm p 1 l ~2.8 ppm d 2 3 l 3 ~2.1 ppm s 3 l ~1.2 ppm d TMS ppm

18 List in tabular form the expected signals for the proton NMR spectrum of D and then sketch that spectrum. proton(s) relative chemical shift (ppm) multiplicity integration ~7.2 ppm m 5 ~3.9 ppm t 2 ~3.2 ppm s 3 ~2.2 ppm t 2 ~1.3 ppm t 2 TMS 0 ppm D

19 List in tabular form the expected signals for the proton NMR spectrum of D and then sketch that spectrum D proton(s) relative chemical shift (ppm) multiplicity integration ~7.2 ppm m 5 t-butyl group 0 2 ppm s 9 2 Ph 2 3 ppm t ppm t 2 t-bu Ph 2 2 TMS ppm

20 List in tabular form the expected signals for the NMR spectrum of A and then sketch that spectrum Br proton A proton(s) relative chemical shift (ppm) multiplicity integration ~7.2 ppm m 5 Br Br Br Br Br ~6.9 ppm d 1 ~6.2 ppm d 1 ~4.2 ppm s 2 ~3.5 ppm q 1 3 Br 3 3 ~1.4 ppm d 3 ~1.0 ppm s TMS ppm

21 The 1 -NMR spectrum below is most likely of: Note: The proton NMR data (including the relative integration) are as follows: the triplet at 3.4 ppm (2), the multiplet at 1.6 ppm (2), and the triplet at 0.9 ppm (3). 3 N 3 l l

22 The 1 -NMR spectrum below is most likely of: Note: The proton NMR data (including the relative integration) are as follows: the doublet at 7.83 ppm (1), the overlapping series peaks from ppm (3), the quartet at 2.90 ppm (2), and the triplet at 1.27 ppm (3) N 2 N 2 N 2 N 2 N N 2

23 The 1 -NMR spectrum below is most likely of: Note: The proton NMR data (including the relative integration) are as follows: the broad singlet at ppm (1), and the singlet at 2.10 ppm (3) F 3

24 The 1 -NMR spectrum below is most likely of: Note: The proton NMR data (including the relative integration) are as follows: the doublet at 7.97 ppm (2), the doublet at 6.89 ppm (2), the singlet at 3.86 ppm (3), and the singlet at 3.82 ppm (3). 2 2

25 The 1 -NMR spectrum below is most likely of: Note: The proton NMR data (including the relative integration) are as follows: the multiplet at 7.25 ppm (2), and the singlet at 2.40 ppm (3). 3 2 Br F F F

26 The 1 -NMR spectrum below is most likely of: Note: The proton NMR data (including the relative integration) are as follows: the broad singlet at 3.78 ppm (1), the triplet at 3.67 ppm (2), the triplet at 3.57 ppm (2), and the pentet at 1.90 ppm (2). l l l l l l

27 The 1 -NMR spectrum below is most likely of: Note: The proton NMR data (including the relative integration) are as follows: the multiplet at 2.58 ppm (1), the quartet at 2.45 ppm (2), the doublet at 1.07 ppm (6), and the triplet at 1.01 ppm (3).

28 The 1 -NMR spectrum below is most likely of: F 3 F 3 3 3

29 The 1 -NMR spectrum below is most likely of: integration:

30 The 1 -NMR spectrum below is most likely of: integration:

31 The IR and proton NMR of compound D are provided below. The mass spec of D provides a molecular formula of Major mass spec fragment peaks are also observed at m/z = 43, 60, and 73. What is the structure of compound D? D Note: The proton NMR data is a follows: 4.1 ppm (triplet, 2), 2.1 ppm (singlet, 3), 1.7 ppm (multiplet, 2), and 0.9 ppm (triplet, 3).

32 The IR and proton NMR of compound E are provided below. The molecular formula of compound E is What is the structure of compound E? E Note: The relative integration for the proton NMR is a follows: the quartet at 4.1 ppm (2), the triplet at 2.2 ppm (2), the multiplet at 1.7 ppm (2), and the triplet at 1.3 ppm (3) and the triplet at 0.9 ppm (3).

33 The IR and proton NMR of compound F are provided below. The molecular formula of compound F is What is the structure of compound F? F Note: The relative integration for the proton NMR is a follows: the triplet at 2.4 ppm (2), the singlet at 2.12 ppm (3), the multiplet at 1.6 ppm (2), and the triplet at 0.91 ppm (3).

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