Which of the labeled protons absorbs energy most upfield in the 1H NMR?

An unknown compound (C₇H₆O) gives the IR spectrum shown here. At what chemical shifts would you expect to see signals in the ¹H NMR spectrum?

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Predict the theoretical number of different NMR signals produced by each compound, and give approximate chemical shifts. Point out any diastereotopic relationships.

c. Ph—CHBr—CH₂Br

d. vinyl chloride

Which pairs are diastereotopic hydrogens?

Predict the theoretical number of different NMR signals produced by each compound, and give approximate chemical shifts. Point out any diastereotopic relationships.

a. 2-bromobutane

b. cyclopentanol

Which of the labeled hydrogens will be most de-shielded?

Which compound possesses a hydrogen with the highest chemical shift for its 1H NMR signal?

Predict the approximate chemical shifts of the protons in the following compounds.

(c) CH₃–O–CH₂CH₂CH₂Cl

(d) CH₃CH₂–C≡C–H