Deduce the structure that fits the given data. • Molecular formula: C,H₁0O • Proton decoupled 13C NMR data: 8 14, 17, 30, 45, 207 ppm • ¹H NMR spectral data: 8 0.9 (t, 3H), 1.60 (m, 5H), 2.10 (s, 3H), 2.40 (t, 2H). Strategy

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Deduce the structure that fits the given data.
• Molecular formula: C₂H₁00
• Proton decoupled 13C NMR data: 8 14, 17, 30, 45, 207 ppm
• ¹H NMR spectral data: 8 0.9 (t, 3H), 1.60 (m, 5H), 2.10 (s, 3H), 2.40 (t, 2H).
Strategy:
Step 1: Calculate the index of hydrogen deficiency or degree of unsaturation from the molecular formula.
Step 2: Determine the number of unique carbons and hydrogens.
Step 3: Identify the diagnostic functional group in the 13C NMR spectrum.
Step 4: Evaluate the potential functional groups and eliminate the group that does not fit the data.
Step 5: Consider the chemical shifts, splitting patterns and integration to determine fragments.
Step 6: Consider the remaining possibilities and determine which matches the data the best.
Step 1: Calculate the index of hydrogen deficiency (IHD) or degree of unsaturation for the unknown compound with the
molecular formula C5H₁0O.
The IHD is
Transcribed Image Text:Macmillan Learning Stacked Deduce the structure that fits the given data. • Molecular formula: C₂H₁00 • Proton decoupled 13C NMR data: 8 14, 17, 30, 45, 207 ppm • ¹H NMR spectral data: 8 0.9 (t, 3H), 1.60 (m, 5H), 2.10 (s, 3H), 2.40 (t, 2H). Strategy: Step 1: Calculate the index of hydrogen deficiency or degree of unsaturation from the molecular formula. Step 2: Determine the number of unique carbons and hydrogens. Step 3: Identify the diagnostic functional group in the 13C NMR spectrum. Step 4: Evaluate the potential functional groups and eliminate the group that does not fit the data. Step 5: Consider the chemical shifts, splitting patterns and integration to determine fragments. Step 6: Consider the remaining possibilities and determine which matches the data the best. Step 1: Calculate the index of hydrogen deficiency (IHD) or degree of unsaturation for the unknown compound with the molecular formula C5H₁0O. The IHD is
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