(1) In the mass spectrum, a compound with two bromine atoms will have:
             A. two molecular ions, in the ratio 1:1
  B. four molecular ions, in the ratio 1:1:1:1
  C. two molecular ions, in the ratio 2:1
  D. four molecular ions, in the ratio 1:2:2:1
  E. three molecular ions, in the ratio 1:2:1
   
(2) In the 1H NMR of diethylether (CH3CH2-O-CH2CH3) the signal from the CH2 protons will appear as:
             A. a triplet
  B. a multiplet consisting of 9 peaks
  C. a multiplet consisting of seven peaks
  D. a multiplet consisting of 6 quartets
  E. a quartet
     
(3) How many peaks will be present in the proton-decoupled 13C NMR of the compound shown on the right:
             A. 4
  B. 3
  C. 5
  D. 7
  E. 6
   
(4) The base peak in the mass spectrum of benzaldehyde is most likely to be due to:
             A.
  B.
  C.
  D.
  E.
   
(5) The major bands in the infrared spectrum of ethyl cyanoacetate will be:
             A. 3150 cm-1; 2200 cm-1; 1610 cm-1
  B. 3450 cm-1; 2930 cm-1; 1760 cm-1
  C. 2930 cm-1; 2450 cm-1; 1610 cm-1
  D. 2930 cm-1; 2200 cm-1; 1750 cm-1
  E. 3010 cm-1; 2200 cm-1; 1750 cm-1
   
(6) Which of the following is not true regarding the spectra of acetophenone:
             A. in the 1H NMR, the CH3 group will appear as a singlet
  B. the 13C NMR will have a singlet at approximately 200 ppm
  C. the IR spectrum will display by a significant absorption at about 2400 cm-1
  D. in the 1H NMR, the CH3 group will absorb at approximately d 2.2
  E. in the mass spectrum, a significant peak will occur at m/e = 43
   
(7) In the NMR, the term ppm (d) refers to:
             A. the precessional path of the nuclear moment of inertia
  B. parts per million
  C. the concentration of the sample divided by 106
  D. the coupling constant, J, divided by the chemical shift of tetramethylsilane (Si(CH3)4)
  E. b and c are both correct.
   
(8) Which of the following compounds would be most consistent with the infrared spectrum shown on the right:
             A.
  B.
  C.
  D.
  E.
   
(9) Which of the following compounds would be most consistent with the NMR spectrum shown on the right:
             A.
  B.
  C.
  D.
  E.
   
(10) Which of the following compounds would be most consistent with the MASS spectrum shown on the right:
             A.
  B.
  C.
  D.
  E.
   
(11) In the mass spectrum, the base peak:
             A. gives the molecular weight of the molecule
  B. represents the most stable Lewis base in the molecule
  C. represents the most reactive cation radical within the molecule
  D. is the most intense peak in the spectrum
  E. is formed by expulsion of the most stable cation radical
   
(12) The 1H NMR of 2-chloropropane will consist of:
             A. a multiplet consisting of ten peaks
  B. a doublet and a septet
  C. a singlet
  D. a quartet
  E. a multiplet consisting of five peaks
   

(13) In the "aromatic" region of the 13C NMR, a symmetrical 1,4-disubstituted aromatic compound will generally display, in a proton-decoupled spectrum:
             A. six peaks
  B. three peaks
  C. four peaks
  D. one singlet and one doublet
  E. two peaks
   
(14) Which of the following is true regarding a proton-decoupled 13C NMR:
             A. carbons bearing one hydrogen will be split into doublets
  B. the integration gives the number of hydrogens attached to the carbon giving rise to the absorption
  C. the signal intensity is not proportional to the number of carbons giving rise to the absorption
  D. splitting from adjacent 13C atoms is suppressed
  E. splitting occurs only from hydrogens directly attached to the carbon giving rise to the absorption
   
(15) The major bands in the infrared spectrum of ethyl propynoate will be:
             A. 3450 cm-1; 2200 cm-1; 1610 cm-1
  B. 3100 cm-1; 2930 cm-1; 2200 cm-1; 1760 cm-1
  C. 2930 cm-1; 2450 cm-1; 1610 cm-1
  D. 2930 cm-1; 2200 cm-1; 1710 cm-1
  E. 3450 cm-1; 3010 cm-1; 2200 cm-1; 1610 cm-1
   
(16) Which of the following is true regarding the spectra of 1-butyne:
             A. the 1H NMR will consist of a quartet and a triplet
  B. the non-decoupled 13C NMR will consist of two singlets
  C. the mass spectrum will be dominated by a peak at M-29
  D. the proton-decoupled 13C NMR will consist of a triplet and a singlet
  E. the IR spectrum will have a significant absorption in the region 2200-2400 cm-1
   
(17) The 1H NMR spectrum of 1,2-dimethoxyethane (CH3-O-CH2CH2-O-CH3) will consist of:
             A. one singlet, d 3.5, area 6, and two triplets, d 3-4, area two each
  B. two singlets in the region d 3-4
  C. one singlet, d 3.5, area 6, and one triplet, d 4.0, area 4
  D. two singlets, d 3-4, area 3 each, and two triplets, also d 3-4, area two each
  E. one singlet, d 3.5, area 6, and one multiplet (5 peaks), d 4.0, area 4
   

(18) In the 1H NMR, the most highly shielded protons which are typically encountered are:
             A. carboxylic acid protons
  B. tert-butyl groups
  C. aromatic protons
  D. alkyne protons
  E. the methyl groups of tetramethyl silane
   
(19) Which of the following is true regarding NMR spectroscopy:
             A. in a magnetic field, nuclei are split equally into high and low spin states
  B. nuclei with non-integer spins give rise to NMR signals
  C. adjacent 13C atoms do not magnetically couple with each other
  D. decoupling is a technique commonly used to enhance the chemical shift of selected atoms
  E. in NMR, ppm is used as an abbreviation for Please P amper the Machine
   
(20) Which of the following is not true regarding infrared spectroscopy:
             A. the carbonyl stretch is highly asymmetric and is therefore a major peak in the IR spectrum
  B. hydroxyl groups give rise to broad absorbance bands due to hydrogen bonding
  C. the "fingerprint region" of the spectrum consists of complex stretching, bending and overtone bands, but is unique for a given molecule
  D. stretching vibrations from symmetrical bonds are not observed in the IR spectrum
  E. higher energy stretching bands occur at lower wave numbers on the cm-1 scale
   
(21) The 1 H NMR spectrum of cyclohexane at room temperature will consist of:
             A. one doublet and one quartet
  B. one singlet
  C. six pairs of doublets and six quartets
  D. one singlet and one doublet
  E. one singlet and one triplet
   
For each of the following compounds (Questions 22-25) , indicate the number of peaks you expect in the aromatic region of the proton-decoupled 13C NMR:
(22) Toluene:
             A. 2
  B. 3
  C. 4
  D. 5
  E. 6
   
(23) 1,3-Dimethylbenzene:
             A. 2
  B. 3
  C. 4
  D. 5
  E. 6
   
(24) 1,4-Dimethylbenzene:
             A. 2
  B. 3
  C. 4
  D. 5
  E. 6
   
(25) 1,3,5-Trimethylbenzene:
             A. 2
  B. 3
  C. 4
  D. 5
  E. 6