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Chapter 14: Q.21558-14-6P. (page 535)

Label the protons in each highlighted CH2 group as enantiotopic, diastereotopic, or homotopic.

a.

b.

c.

Short Answer

Expert verified

a. Enantiotopic

b. Neither

c. Diastereotopic

Step by step solution

01

Homotopic, enantiotopic, and diastereotopic protons

鈥� Homotopic protons are formed when the same product is formed by the substitution of two H by Z.

鈥� Enantiotopic protons are formed when two H are equivalent and occur at the same NMR signal.

鈥� Diastereotopic protons are formed when two H are not equivalent and occur at two different signals.

02

Explanation for highlighted proton

a.

The replacement of H with X is shown below.

Enantiotopic proton

b.

The replacement of H with X is shown below.

Neither enantiotopic nor diastereotopic

c.

The replacement of H with X is shown below.

Diastereotopic proton

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Most popular questions from this chapter

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

Question:Answer the following questions about each of the hydroxy ketones: 1-hydroxybutan-2-one (A) and 4-hydroxybutan-2-one (B).

a. What is the molecular ion in the mass spectrum?

b. What IR absorptions are present in the functional group region?

c. How many lines are observed in the 13C NMR spectrum?

d. How many signals are observed in the 1H NMR spectrum?

e. Give the splitting observed for each type of proton as well as its approximate chemical shift.

Question: Identify the structures of isomers E and F (molecular formula C4H802 ). Relative areas are given above each signal.

a.

b.

Describe the 1HNMR spectrum of each compound. State how many NMR signals are present, the splitting pattern for each signal, and the approximate chemical shift.

a.

b.

c.

d.

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

a.

b.

c.

d.

e.

f.

g.

h.

i.

j.
See all solutions

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