Title: CHE2FND_Spectroscopy_old

Q: Of the 4 compounds shown below, which is the only one that will exhibit a peak at ~2100 cm^-1 in its I.R. spectrum?
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Q: Compound y was found to have a M_w = 146 g.mol^-1. Combustion analysis was performed, and the results have been shown below:

C 49.3%
H 9.6%
N 19.2%

From this data, the empirical formula and molecular formula were determined to be:
- C_6H_14N_2O_2 and C_6H_14N_2O_2
- C_3H_7NO and C_6H_14N_2O_2
- C_3H_7NO and C_12H_28N_4O_4
- C_6H_14N_2O_2 and C_12H_28N_2O_4
A: C_3H_7NO and C_6H_14N_2O_2

Q: A combustion analysis was conducted on compound x and was found to be:

C 61.3%
H 5.1%
N 10.2%

From the above data, the correct empirical formula was determined to be:
- C_7H_7N
- C_5H_5N
- C_7H_7NO_2
- C_5H_5NO_2
A: C_7H_7NO_2

Q: It was confirmed by IR spectroscopy that compound v possessed a carbonyl group in its structure. At what wavenumber would this confirmation most likely have been made?
- 3500 cm^-1, broad, strong intensity
- 1700 cm^-1, sharp, strong intensity
- 1600 cm^-1, sharp, medium intensity
- 2100 cm^-1, sharp, weak intensity
A: 1700 cm^-1, sharp, strong intensity

Q: Where would 1-cyano propanol exhibit peaks in its I.R. spectrum?
- 3300 cm^-1, 2960 cm^-1, 1700 cm^-1
- 3300-3600 cm^-1, 3100 cm^-1, 2225 cm^-1
- 3300 cm^-1, 2700-3000 cm^-1, 2225^ cm^-1
- 3300-3600 cm^-1, 2960 cm^-1, 2225 cm^-1
A: 3300-3600 cm^-1, 2960 cm^-1, 2225 cm^-1

Q: What type and instensity of stretches would be identified in an unsaturated secondary amine possessing conjugated carbon-carbon double bonds?
- One stretch of medium intensity for the amine and one stretch of medium intensity for the carbon-carbon double bond.
- Two stretches of medium intensity for the amine and one stretch of medium intensity for the carbon-carbon double bond.
- One stretch of medium intensity for the amine and one stretch of low intensity for the carbon-carbon double bond.
- Two stretches of medium intensity for the amine and one stretch of low intensity for the carbon-carbon double bond.
A: One stretch of medium intensity for the amine and one stretch of medium intensity for the carbon-carbon double bond.

Q: The molecular formula of compound z was C_14H_11Cl_2NO. How many double bond equivalents are in this structure?
- 10
- 9
- 7
- 8
A: 9

Q: The I.R. spectrum of compound g exhibited peaks at:

~2960 cm^-1
~2800 cm-1
~2720 cm-1
~1710 cm-1
- 3-pentanone
- pentanaldehyde
- 2-pentanone
- pentanoic acid
A: pentanaldehyde

Q: The molecular formula of compound z was C_14H_11Cl_2NO. How many double bond equivalents are in this structure?
- 9
- 10
- 7
- 8
A: 9

Q: Compound u was found to contain a primary amide functional group via IR spectroscopy. How would this signal(s) be expected to appear in an IR spectrum?
- 1 peak at ~1700 cm^-1 and 2 peaks at ~3500 cm^-1
- 2 peaks at ~1700 cm^-1 and 2 peaks at ~3500 cm^-1
- 2 peaks at ~1700 cm^-1 and 1 peak at ~3500 cm^-1
- 1 peak at ~1700 cm^-1 and 1 peak at ~3500 cm^-1
A: 2 peaks at ~1700 cm^-1 and 2 peaks at ~3500 cm^-1

Q: At what chemical shift would a mono-substituted phenyl ring be expected to occur at?
- ~4.8 ppm
- ~1.3 ppm
- ~7.2 ppm
- ~11.5 ppm
A: ~7.2 ppm

Q: Compound y was found to have a M_w = 146 g.mol^-1. Combustion analysis was performed, and the results have been shown below:

C 49.3%
H 9.6%
N 19.2%

From this data, the empirical formula and molecular formula were determined to be:
- C_3H_7NO and C_6H_14N_2O_2
- C_6H_14N_2O_2 and C_12H_28N_2O_4
- C_3H_7NO and C_12H_28N_4O_4
- C_6H_14N_2O_2 and C_6H_14N_2O_2
A: C_3H_7NO and C_6H_14N_2O_2

Q: Of the 4 hydrocarbon chains shown below, which one would be expected to give rise to 3 signals in a ^1H NMR spectrum; seen as a triplet, sextet and triplet, respectively?
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A: [Image: question14c]

Q: After complete characterisation, compound s was identified as isopropylbenzene. The integration ratio of the isopropyl group was determined to be:
- 3:6
- 1:3
- 2:6
- 1:6
A: 1:6

Q: Which structure below represents the molecular formula C_18H_15O_2Cl_2N?
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A: [Image: question3a]

Q: The structure of a butterfly's sex pheromone has been shown below:

[Image: question5]

How many double bond equivalents are present in this structure?
- 4
- 3
- 5
- 6
A: 5

Q: Which of the compounds represented below has 6 double bond equivalents?
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A: [Image: question6a]

Q: Which of the compounds represented below has 6 double bond equivalents?
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A: [Image: question6a]

Q: Characterisation of compound w was conducted using IR spectroscopy. A sharp peak of medium intensity was identified at ~3300 cm^-1. It was concluded this peak would most likely correspond to:
- an aliphatic [Image: question7d] stretch
- a [Image: question7c] stretch
- a [Image: question7b] stretch
- a [Image: question7a] stretch
A: a [Image: question7a] stretch

Q: Compound t was found to possess major IR absorption peaks at ~3100 cm^-1, ~3000 cm^-1 and ~1650 cm^-1 respectively. Which structure was the compound concluded to be?
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A: [Image: question10a]

Q: A poorly labelled sample of a chemical was found in the lab. The label contained the following information:

Molecular Weight = 286 Da

IR data = 2900-3300 cm^-1
~3100 cm^-1
~3000 cm^-1
~1700 cm^-1
~1650 cm^-1

Which of the 4 lactones shown below was the poorly labelled sample?
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A: [Image: specadv1d]

Q: Of the 4 compounds shown below, which is the only one that will exhibit a peak at ~2100 cm^-1 in its I.R. spectrum?
- [Image: question15d]
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A: [Image: question15b]

Q: A chemist was analysing the ^1H NMR spectrum of the compound shown below:

[Image: question11]

One of the 4 signals was seen to have a chemical shift of ~3.7 ppm. This signal would most likely be assigned to:
- The methoxy OCH_3 protons (4)
- The methylene CH_2 protons next to the aldehyde (2)
- The aldehyde proton (1)
- The methylene CH_2 protons next to the methoxy OCH_3 group (3)
A: The methoxy OCH_3 protons (4)

Q: Compound m was identified using ^1H NMR spectroscopy to be the meta-disubstituted aromatic ring shown below:

[Image: question15]

The substitution pattern of the hydrogens connected to the aromatic ring was found to be:
- One singlet, one doublet and two triplets
- One singlet, one doublet, one triplet and one quartet
- Two singlets and two doublets
- One singlet, two doublets and one triplet
A: One singlet, two doublets and one triplet

Q: The structure of a butterfly's sex pheromone has been shown below:

[Image: question5]

How many double bond equivalents are present in this structure?
- 6
- 5
- 4
- 3
A: 5