Sample Exam-2 - 2 I Answer the following questions true or...

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2 I. Answer the following questions true or false (3 pts each). (1) False Diastereotopic hydrogen must show identical chemical shifts on an NMR spectrum. (2) True The three hydrogen of a methyl group show identical chemical shifts on an NMR spectrum. (3) False The chemical shift reveals the relative number of equivalent hydrogen atoms present in a molecule. (4) False Six distinct signals will be observed for the protons of benzene (C 6 H 6 ) on an 1 H NMR spectrum that is obtained at 50 K. (5) True The coupling constant for protons attached to adjacent carbon atoms is independent of the strength of the magnetic field to which they are exposed. (6) False Addition of D 2 O to a sample of cyclohexane will cause identical shifts to be observed for the axial and equatorial hydrogen atoms of the six member ring. (7) True The protons of a benzene ring are normally more deshielded than the protons of a simple alkane. (8) True Carboxylic acids form cyclic intermolecular hydrogen bonds that cause a broadening of the O-H stretching peak for an IR spectra. (9) True The chemical shift of tetramethylsilane is normally defined as δ = 0 (10) False The IR stretching frequency depends upon the change in the dipole moment of the bond that occurs upon stretching. Score page 2
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3 (II) (A) Write the name of the functional group from the list given below that is illustrated in each of three IR spectra on the handout (5 points each). Nitrile Amine Ketone Alkyl chloride Alkyl alcohol Alkene Aldehyde Amide Carboxylic acid Alkyne (A) Aldehyde (B) Alcohol (C) Carboxylic Acid Score - Page 3
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4 (B) Predict the multiplicity of peaks (singlet, doublet, triplet etc) for each of the labeled protons in the following molecule (5 pts/each).
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