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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

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

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

• 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

Propose a structure consistent with each set of data.

a. C9H10O2: IR absorption at 1718cm-1

b. C9H12 : IR absorption at 2850–3150cm-1

a. How many signals does dimethyl fumarate (\({\bf{C}}{{\bf{H}}_{\bf{3}}}{{\bf{O}}_{\bf{2}}}{\bf{CCH = CHC}}{{\bf{O}}_{\bf{2}}}{\bf{C}}{{\bf{H}}_{\bf{3}}}\) with a trans C=C) exhibit in its \(^{{\bf{13}}}{\bf{C}}\) NMR spectrum?

b. Draw the structure of an isomer of dimethyl fumarate that has each of the following number of signals in its \(^{{\bf{13}}}{\bf{C}}\) NMR spectrum:\(\left( {\bf{1}} \right)\) three; \(\left( {\bf{2}} \right)\) four; \(\left( {\bf{5}} \right)\) five

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

a.

b.

Question: How many different types of protons are present in each compound?

Question: (a) How many 1H NMR signals does each of the following compounds exhibit? (b) How many 13C NMR signals does each compound exhibit?
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