7. Suggest chemical structures for compounds A, B, and C, and answer the subsequent spectroscopy question Et 1. NaH Na,Cr207 LIAIHA (2 equiv) A в H2SO4, H20 Ét then H2O/N2OH 2. CH3Í (2 equiv) (a) Provide structures for compounds A, B, and C. [Hint: Compound C has the formula C10H1402, M* = 166 ] (b) Compound C has the following 'H NMR chemical shifts: 8 3.36 (s, 6H), 4.43 (s, 4H), 7.31 (s, 4H). Label the chemically-inequivalent protons as HA, HB, Hc, etc. and clearly assign the chemical shifts. (c) Compound C has the following13C NMR chemical shifts: 8 58, 75, 128, 138. Label the chemically-inequivalent carbons as C1, C2, C3, and C4 and assign the chemical shifts

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Chapter1: Chemical Foundations
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7. Suggest chemical structures for compounds A, B,
and C, and answer the subsequent spectroscopy
question
Et
1. NaH
Na,Cr207
LIAIHA
(2 equiv)
A
в
H2SO4, H20
Ét
then
H2O/N2OH
2. CH3I
(2 equiv)
(a) Provide structures for compounds A, B, and C.
[Hint: Compound C has the formula C10H1402, M* = 166 ]
(b) Compound C has the following 'H NMR chemical shifts:
8 3.36 (s, 6H), 4.43 (s, 4H), 7.31 (s, 4H).
Label the chemically-inequivalent protons as HA, HB, Hc, etc.
and clearly assign the chemical shifts.
(c) Compound C has the following13C NMR chemical shifts:
8 58, 75, 128, 138.
Label the chemically-inequivalent carbons as C1, C2, C3, and
C4 and assign the chemical shifts
(d) How could you use IR spectroscopy to confirm that
compound B has reacted to form compound C?
(e) Sketch the isotopic cluster for the mass spectrum of C.
(e.g., What would the mass spectrum look like?)
Transcribed Image Text:7. Suggest chemical structures for compounds A, B, and C, and answer the subsequent spectroscopy question Et 1. NaH Na,Cr207 LIAIHA (2 equiv) A в H2SO4, H20 Ét then H2O/N2OH 2. CH3I (2 equiv) (a) Provide structures for compounds A, B, and C. [Hint: Compound C has the formula C10H1402, M* = 166 ] (b) Compound C has the following 'H NMR chemical shifts: 8 3.36 (s, 6H), 4.43 (s, 4H), 7.31 (s, 4H). Label the chemically-inequivalent protons as HA, HB, Hc, etc. and clearly assign the chemical shifts. (c) Compound C has the following13C NMR chemical shifts: 8 58, 75, 128, 138. Label the chemically-inequivalent carbons as C1, C2, C3, and C4 and assign the chemical shifts (d) How could you use IR spectroscopy to confirm that compound B has reacted to form compound C? (e) Sketch the isotopic cluster for the mass spectrum of C. (e.g., What would the mass spectrum look like?)
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