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Chapter 14: Q.21558-14-30P. (page 558)

Which of the highlighted carbon atoms in each molecule absorbs farther downfield?

a.

b.

c.

d.

Short Answer

Expert verified

a.

b.

c.

d.

Step by step solution

01

Upfield and Downfield in 13C NMR

The carbon atoms that absorb downfield are the ones that shows signal to the left of the NMR spectrum (higher chemical shifts).

The carbon atoms that absorb upfield are the ones that shows signal to the farther right of the NMR spectrum (lower chemical shifts).

02

Downfield shift in 13C NMR

鈥� The presence of electronegative elements shifts the absorptions downfield.

鈥� The sp2 hybridized carbon atoms show downfield absorptions.

鈥� All the electron deficient carbon atoms (for example the carbonyl carbon) shows downfield absorptions.

03

Carbon atoms showing downfield absorptions in the given compounds.

a.

Carbon atom absorbing downfield in a.

The carbon atom adjacent to the oxygen atom is electron-deficient and hence it absorbs downfield.

b.

Carbon atom absorbing downfield in b.

The carbon atom bonded to two bromine atoms is highly electron-deficient compared to the other and hence it absorbs farther downfield.

c.

Carbon atom absorbing downfield in c.

The carbonyl carbon absorbs downfield.

d.

Carbon atom absorbing downfield in d.

The double-bonded carbon ( hybridized) absorbs farther downfield.

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Most popular questions from this chapter

Question: What effect does increasing the operating frequency of a1HNMR spectrum have on each value: (a) the chemical shift in未 ;(b) the frequency of an absorption in Hz; (c) the magnitude of a coupling constant J in Hz?

Question: Explain why the carbonyl carbon of an aldehyde or ketone absorbs farther downfield than the carbonyl carbon of an ester in a 13C NMR spectrum

Question: How many \(^{\bf{1}}{\bf{H}}\) NMR signals does each dimethylcyclopropane show?

a.

b.

c.

Question: Into how many peaks will the signal for each of the labeled protons be split?

Identify the carbon atoms that give rise to the signals in the \)^{{\bf{13}}}{\bf{C}}\) NMR spectrum of each compound.

a. \){\bf{C}}{{\bf{H}}_{\bf{3}}}{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{OH}}\); \)^{{\bf{13}}}{\bf{C}}\) NMR: 14, 19, 35, and 62 ppm

b. \){\left( {{\bf{C}}{{\bf{H}}_{\bf{3}}}} \right)_{\bf{2}}}{\bf{CHCHO}}\); \)^{{\bf{13}}}{\bf{C}}\) NMR: 16, 41, and 205 ppm

c. \){\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{ = CHCH}}\left( {{\bf{OH}}} \right){\bf{C}}{{\bf{H}}_{\bf{3}}}\); \)^{{\bf{13}}}{\bf{C}}\) NMR: 23, 69, 113, and 143 ppm
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