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Infrared / NMR Spectroscopy Questions
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Is the following IR of cis or trans 2-pentene?
Question 1 Is the following IR of cis or trans 2-pentene? cis B) trans
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Is the following IR of cis or trans 2-pentene? B) trans 2-pentene
Answer Is the following IR of cis or trans 2-pentene? B) trans 2-pentene
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Question 2 Identify the compound from the IR above. benzyl alcohol
C7H6O Identify the compound from the IR above. benzyl alcohol 1,4,6-heptatrien-3-one 2,4,6-heptatrienaldehyde benzaldehyde
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Answer D) Benzaldehyde wavenumber (cm–1) assignment 2810 and 2730
1700 an aldehyde mono subs benzene carbonyl
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Question 3 Identify the compound from the IR above.
C10H12O Identify the compound from the IR above. 4-phenylbutanaldehyde phenylpropyl ketone meta-isopropylbenzaldehyde 1-phenyl-2-butanone
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non-conj ketone carbonyl
Answer D) 1-phenyl-2-butanone wavenumber (cm–1) assignment >3000 <3000 740 and 700 1720 sp2 CH sp3 CH Mono subs benzene ring non-conj ketone carbonyl
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Question 4 Identify the compound from the IR above. cyclopropanone
C3H4O Identify the compound from the IR above. cyclopropanone propynol 2-cyclopropenol 1,2-propadienol
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Answer B) propynol wavenumber (cm–1) assignment 3300 OH group 2950
2100 OH group sp3 CH alkyne
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Question 5 Identify the compound from the IR above. N-methylacetamide
C3H7NO Identify the compound from the IR above. N-methylacetamide N,N-dimethylformamide 3-aminopropanal N-methylamino-ethanal
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Answer N-methylacetamide wavenumber (cm–1) assignment 3300 N–H 1660
amide carbonyl
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Question 6 I II III Match the ortho, meta and para isomers of xylene.
B) C) D)
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Answer I II III Ortho 735-770 Para 790-840 Meta 750-810 and 680-730 C)
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Question 7 Identify the compound from the IR above. methylbenzoate
C8H8O2 Identify the compound from the IR above. methylbenzoate phenylacetate p-anisaldehyde o-anisaldehyde
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Answer Identify the compound from the IR above. methylbenzoate
Phenylacetate p-anisaldehyde o-anisaldehyde
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Question 8 Which proton is most shielded? A) CHCl3 B) CH2Cl2 C) CHBr3
D) CBr4
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Answer Which proton is most shielded? A) CHCl3 B) CH2Cl2 C) CHBr3
D) CBr4
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Question 9 Select the most shielded proton in 1,1,2-trichlorobutane.
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Answer Select the most shielded proton in 1,1,2-trichlorobutane. A) 1
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Question 10 Assign the chemical shifts d 1.6,
d 2.2, and d 4.8 to the appropriate protons of methylene cyclopentane. A) x = 1.6; y = 2.2; z = 4.8 B) x = 4.8; y = 1.6; z = 2.2 C) x = 1.6; y = 4.8; z = 2.2 D) x = 2.2; y = 1.6; z = 4.8
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Answer Assign the chemical shifts d 1.6,
d 2.2, and d 4.8 to the appropriate protons of methylene cyclopentane. A) x = 1.6; y = 2.2; z = 4.8 B) x = 4.8; y = 1.6; z = 2.2 C) x = 1.6; y = 4.8; z = 2.2 D) x = 2.2; y = 1.6; z = 4.8
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Question 11 Assign the chemical shifts d1.1,
d2.4, and d9.7 to the appropriate protons of propanal. A) x = 2.4; y = 1.1; z = 9.7 B) x = 1.1; y = 9.7; z = 2.4 C) x = 9.7; y = 2.4; z = 1.1 D) x = 1.1; y = 2.4; z = 9.7
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Answer Assign the chemical shifts d1.1,
d2.4, and d9.7 to the appropriate protons of propanal. A) x = 2.4; y = 1.1; z = 9.7 B) x = 1.1; y = 9.7; z = 2.4 C) x = 9.7; y = 2.4; z = 1.1 D) x = 1.1; y = 2.4; z = 9.7
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Question 12 A compound with the formula C6H14O has the following signal integration for 3 signals: A, B, and C. How many protons are represented by each signal? A. Signal at 0.9, integration of 6.3 B. Signal at 1.4, integration of 4.2 C. Signal at 3.5, integration of 4.2 A = 3; B = 4; C = 4 A = 3; B = 2; C = 2 A = 6; B = 2; C = 2 A = 6; B = 4; C = 4
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Answer A compound with the formula C6H14O has the following signal integration for 3 signals: A, B, and C. How many protons are represented by each signal? A. Signal at 0.9, integration of 6.3 B. Signal at 1.4, integration of 4.2 C. Signal at 3.5, integration of 4.2 A = 3; B = 4; C = 4 A = 3; B = 2; C = 2 A = 6; B = 2; C = 2 A = 6; B = 4; C = 4
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