Question 1

Which of the following does not involve the interaction of molecules with electromagnetic energy?

Accepted Answer

A)  mass spectrometry 
B)  infrared spectroscopy 
C)  ultraviolet spectroscopy 
D)  nuclear magnetic resonance spectroscopy 
A)  mass spectrometry 
B)  infrared spectroscopy 
C)  ultraviolet spectroscopy 
D)  nuclear magnetic resonance spectroscopy

Question 2

Instructions: For each of the compounds below tell how many signals you would expect the molecule to have in its normal, broadband decoupled S1U1P113S1S1P0C NMR spectra.
-Number of signals:

Accepted Answer

The answer of Instructions: For each of the compounds below...

Question 3

Treatment of tert-butyl alcohol with hydrogen chloride yields a mixture of tert-butyl chloride and 2-methylpropene.   a)After chromatographic separation, how would you use 1H NMR to help you decide which was which?
b)How would the 13C NMR for the two compounds differ?

Accepted Answer

a)2-Methylpropene has two kinds of hydro

Question 4

Which structure of molecular formula C4H8Cl2 fits the 1H NMR and 13C NMR spectra shown below?     (Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/)

Accepted Answer

A)   
B)   
C)   
D)   
A)   
B)   
C)   
D)

Question 5

Which feature in the 1H NMR spectrum provides information about the relative numbers of hydrogen atoms of each type found in a compound?

Accepted Answer

A)  number of signals 
B)  integration of signals 
C)  splitting of signals 
D)  chemical shift 
A)  number of signals 
B)  integration of signals 
C)  splitting of signals 
D)  chemical shift

Question 6

Instructions: Match each of the following groups of bond-types to the region of the infrared spectrum in which their absorptions occur.

-C-C, C-O, C-N, and C-X single-bond vibrations.

Accepted Answer

A) 4000 to 2500 cm-1 
B) 2500 to 2000 cm-1 
C) 2000 to 1500 cm-1 
D) below 1500 cm-1 
A) 4000 to 2500 cm-1 
B) 2500 to 2000 cm-1 
C) 2000 to 1500 cm-1 
D) below 1500 cm-1

Question 7

Instructions: Answer the following question(s) for the compound whose S1U1P11S1S1P0H NMR spectra is shown below.
CS1U1B14S1U1B0HS1U1B18S1U1B0O   (Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/)
-Refer to instructions. Propose a structure for this compound.

Accepted Answer

butan-2-on

Question 8

Which of the following combinations of peaks appears in the 1H NMR spectrum of 2-methylpropane?

Accepted Answer

A)  two singlets 
B)  a singlet and a nonet 
C)  a singlet and a decet 
D)  a doublet and a decet 
A)  two singlets 
B)  a singlet and a nonet 
C)  a singlet and a decet 
D)  a doublet and a decet

Question 9

Instructions: Refer to the structure of 3-methylbutan-2-one below to answer the following question(s).  
-Refer to instructions. What is the splitting pattern for the hydrogens in 3-methylbutan-2-one labeled A, B, and C, respectively?

Accepted Answer

A)  singlet, singlet, singlet 
B)  singlet, septet, quartet 
C)  singlet, septet, doublet 
D)  singlet, septet, doublet, doublet 
A)  singlet, singlet, singlet 
B)  singlet, septet, quartet 
C)  singlet, septet, doublet 
D)  singlet, septet, doublet, doublet

Question 10

Which of the following regions in the electromagnetic spectrum corresponds to the radiation with the highest energy?

Accepted Answer

A)  radio waves 
B)  ultraviolet 
C)  infrared 
D)  visible 
A)  radio waves 
B)  ultraviolet 
C)  infrared 
D)  visible

Question 11

Which of the following compounds gives an infrared spectrum with a peak at strong 1730 cm-1?

Accepted Answer

A)   
B)   
C)   
D)   
A)   
B)   
C)   
D)

Question 12

When 2-bromopropane reacts with ethoxide ion, two products are formed; one is the product of SN2 substitution and the other is the product of E2 elimination. Write the structures of both products, and tell how they could be distinguished using IR spectroscopy.

Accepted Answer

Question 13

Which of the following compounds gives an infrared spectrum with peaks at 3000-3500 cm-1 and ~1750 cm-1?

Accepted Answer

A)   
B)   
C)   
D)   
A)   
B)   
C)   
D)

Question 14

Instructions: For each of the compounds below tell how many signals you would expect the molecule to have in its normal, broadband decoupled S1U1P113S1S1P0C NMR spectra.
-Number of signals:

Accepted Answer

The answer of Instructions: For each of the compounds below...

Question 15

Which of the following combinations of peaks appears in the 1H NMR spectrum of diethyl ether, CH3CH2OCH2CH3?

Accepted Answer

A)  a triplet and a doublet 
B)  a quartet and a sextet 
C)  two singlets 
D)  a triplet and a quartet 
A)  a triplet and a doublet 
B)  a quartet and a sextet 
C)  two singlets 
D)  a triplet and a quartet

Question 16

When an organic molecule is irradiated with ultraviolet radiation, the energy absorbed by the molecule corresponds to:

Accepted Answer

A)  the amount necessary to increase molecular motions in functional groups 
B)  the amount necessary to excite electrons from one molecular orbital to another 
C)  the amount necessary to "flip" the spin of atomic nuclei 
D)  the amount necessary to strip a molecule of one electron to generate a radical cation 
A)  the amount necessary to increase molecular motions in functional groups 
B)  the amount necessary to excite electrons from one molecular orbital to another 
C)  the amount necessary to "flip" the spin of atomic nuclei 
D)  the amount necessary to strip a molecule of one electron to generate a radical cation

Question 17

Which of the following compounds would produce the most downfield signal in a 13C NMR spectrum?

Accepted Answer

A)  A 
B)  B 
C)  C 
D)  D 
A)  A 
B)  B 
C)  C 
D)  D

Question 18

Examining the infrared spectrum of a compound allows us to:

Accepted Answer

A)  determine the types of functional groups present in the compound 
B)  determine the carbon-hydrogen framework of the compound 
C)  determine the molecular weight of the compound 
D)  determine the nature of the conjugated pi electron system in the compound 
A)  determine the types of functional groups present in the compound 
B)  determine the carbon-hydrogen framework of the compound 
C)  determine the molecular weight of the compound 
D)  determine the nature of the conjugated pi electron system in the compound

Question 19

Circle any of the following compounds that would be a candidate to produce a UV absorption spectrum.

Accepted Answer

The answer of Circle any of the following compounds that...

Question 20

Which of the following compounds would show the longest wavelength $\lambda$max in its UV spectrum?

Accepted Answer

A)   
B)   
C)   
D)   
A)   
B)   
C)   
D)

Which of the following does not involve the interaction of molecules with electromagnetic energy?

Instructions: For each of the compounds below tell how many signals you would expect the molecule to have in its normal, broadband decoupled ¹³C NMR spectra. -Number of signals:

Treatment of tert-butyl alcohol with hydrogen chloride yields a mixture of tert-butyl chloride and 2-methylpropene. a)After chromatographic separation, how would you use ¹H NMR to help you decide which was which? b)How would the ¹³C NMR for the two compounds differ?

Which structure of molecular formula C₄H₈Cl₂ fits the ¹H NMR and ¹³C NMR spectra shown below? (Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/)

Which feature in the ¹H NMR spectrum provides information about the relative numbers of hydrogen atoms of each type found in a compound?

Instructions: Match each of the following groups of bond-types to the region of the infrared spectrum in which their absorptions occur. -C-C, C-O, C-N, and C-X single-bond vibrations.

Instructions: Answer the following question(s) for the compound whose ¹H NMR spectra is shown below. C₄H₈O (Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/) -Refer to instructions. Propose a structure for this compound.

Which of the following combinations of peaks appears in the ¹H NMR spectrum of 2-methylpropane?

Instructions: Refer to the structure of 3-methylbutan-2-one below to answer the following question(s). -Refer to instructions. What is the splitting pattern for the hydrogens in 3-methylbutan-2-one labeled A, B, and C, respectively?

Which of the following regions in the electromagnetic spectrum corresponds to the radiation with the highest energy?

Which of the following compounds gives an infrared spectrum with a peak at strong 1730 cm^-¹?

When 2-bromopropane reacts with ethoxide ion, two products are formed; one is the product of S_N2 substitution and the other is the product of E2 elimination. Write the structures of both products, and tell how they could be distinguished using IR spectroscopy.

Which of the following compounds gives an infrared spectrum with peaks at 3000-3500 cm^-¹ and ~1750 cm^-¹?

Instructions: For each of the compounds below tell how many signals you would expect the molecule to have in its normal, broadband decoupled ¹³C NMR spectra. -Number of signals:

Which of the following combinations of peaks appears in the ¹H NMR spectrum of diethyl ether, CH₃CH₂OCH₂CH₃?

When an organic molecule is irradiated with ultraviolet radiation, the energy absorbed by the molecule corresponds to:

Which of the following compounds would produce the most downfield signal in a ¹³C NMR spectrum?

Examining the infrared spectrum of a compound allows us to:

Circle any of the following compounds that would be a candidate to produce a UV absorption spectrum.

Which of the following compounds would show the longest wavelength $\lambda$ _max in its UV spectrum?

Structure and Bonding:acids and Bases

Alkanes: the Nature of Organic Compounds

Alkenes and Alkynes: the Nature of Organic Reactions

Reactions of Alkenes and Alkynes

Aromatic Compounds

Sterechemistry at Tetrahedral Centers

Organohalides: Nucleophilic Substitutions and Eliminations

Alcohols, Phenols, Ethers, and Their Sulfur Analogs

Aldehydes and Ketones: Nucleophilic Addition Reactions

Carboxylic Acids and Derivatives: Nucleophilic Acyl Substitution Reactions

Carbonyl Alpha-Substitution Reactions and Condensation Reactions

Amines

Biomolecules: Carbohydrates

Biomolecules: Amino Acids, Peptides, and Proteins

Biomolecules: Lipids and Nucleic Acids

The Organic Chemistry of Metabolic Pathways

Filters

Exam 13: Structure Determination

Which of the following does not involve the interaction of molecules with electromagnetic energy?

Instructions: For each of the compounds below tell how many signals you would expect the molecule to have in its normal, broadband decoupled 13C NMR spectra. -Number of signals:

Treatment of tert-butyl alcohol with hydrogen chloride yields a mixture of tert-butyl chloride and 2-methylpropene. a)After chromatographic separation, how would you use 1H NMR to help you decide which was which? b)How would the 13C NMR for the two compounds differ?

Which structure of molecular formula C4H8Cl2 fits the 1H NMR and 13C NMR spectra shown below? (Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/)

Which feature in the 1H NMR spectrum provides information about the relative numbers of hydrogen atoms of each type found in a compound?

Instructions: Match each of the following groups of bond-types to the region of the infrared spectrum in which their absorptions occur. -C-C, C-O, C-N, and C-X single-bond vibrations.

Instructions: Answer the following question(s) for the compound whose 1H NMR spectra is shown below. C4H8O (Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/) -Refer to instructions. Propose a structure for this compound.

Which of the following combinations of peaks appears in the 1H NMR spectrum of 2-methylpropane?

Instructions: Refer to the structure of 3-methylbutan-2-one below to answer the following question(s). -Refer to instructions. What is the splitting pattern for the hydrogens in 3-methylbutan-2-one labeled A, B, and C, respectively?

Which of the following regions in the electromagnetic spectrum corresponds to the radiation with the highest energy?

Which of the following compounds gives an infrared spectrum with a peak at strong 1730 cm-1?

When 2-bromopropane reacts with ethoxide ion, two products are formed; one is the product of SN2 substitution and the other is the product of E2 elimination. Write the structures of both products, and tell how they could be distinguished using IR spectroscopy.

Which of the following compounds gives an infrared spectrum with peaks at 3000-3500 cm-1 and ~1750 cm-1?

Instructions: For each of the compounds below tell how many signals you would expect the molecule to have in its normal, broadband decoupled 13C NMR spectra. -Number of signals:

Which of the following combinations of peaks appears in the 1H NMR spectrum of diethyl ether, CH3CH2OCH2CH3?

When an organic molecule is irradiated with ultraviolet radiation, the energy absorbed by the molecule corresponds to:

Which of the following compounds would produce the most downfield signal in a 13C NMR spectrum?

Examining the infrared spectrum of a compound allows us to:

Circle any of the following compounds that would be a candidate to produce a UV absorption spectrum.

Which of the following compounds would show the longest wavelength λ\lambdaλ max in its UV spectrum?

Structure and Bonding:acids and Bases

Alkanes: the Nature of Organic Compounds

Alkenes and Alkynes: the Nature of Organic Reactions

Reactions of Alkenes and Alkynes

Aromatic Compounds

Sterechemistry at Tetrahedral Centers

Organohalides: Nucleophilic Substitutions and Eliminations

Alcohols, Phenols, Ethers, and Their Sulfur Analogs

Aldehydes and Ketones: Nucleophilic Addition Reactions

Carboxylic Acids and Derivatives: Nucleophilic Acyl Substitution Reactions

Carbonyl Alpha-Substitution Reactions and Condensation Reactions

Amines

Biomolecules: Carbohydrates

Biomolecules: Amino Acids, Peptides, and Proteins

Biomolecules: Lipids and Nucleic Acids

The Organic Chemistry of Metabolic Pathways

Filters

Instructions: For each of the compounds below tell how many signals you would expect the molecule to have in its normal, broadband decoupled ¹³C NMR spectra. -Number of signals:

Treatment of tert-butyl alcohol with hydrogen chloride yields a mixture of tert-butyl chloride and 2-methylpropene. a)After chromatographic separation, how would you use ¹H NMR to help you decide which was which? b)How would the ¹³C NMR for the two compounds differ?

Which structure of molecular formula C₄H₈Cl₂ fits the ¹H NMR and ¹³C NMR spectra shown below? (Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/)

Which feature in the ¹H NMR spectrum provides information about the relative numbers of hydrogen atoms of each type found in a compound?

Instructions: Answer the following question(s) for the compound whose ¹H NMR spectra is shown below. C₄H₈O (Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/) -Refer to instructions. Propose a structure for this compound.

Which of the following combinations of peaks appears in the ¹H NMR spectrum of 2-methylpropane?

Which of the following compounds gives an infrared spectrum with a peak at strong 1730 cm^-¹?

When 2-bromopropane reacts with ethoxide ion, two products are formed; one is the product of S_N2 substitution and the other is the product of E2 elimination. Write the structures of both products, and tell how they could be distinguished using IR spectroscopy.

Which of the following compounds gives an infrared spectrum with peaks at 3000-3500 cm^-¹ and ~1750 cm^-¹?

Instructions: For each of the compounds below tell how many signals you would expect the molecule to have in its normal, broadband decoupled ¹³C NMR spectra. -Number of signals:

Which of the following combinations of peaks appears in the ¹H NMR spectrum of diethyl ether, CH₃CH₂OCH₂CH₃?

Which of the following compounds would produce the most downfield signal in a ¹³C NMR spectrum?

Which of the following compounds would show the longest wavelength $\lambda$ _max in its UV spectrum?