How many distinct signals would you expect to see in the ¹H NMR spectrum of the following molecules? [Ignore diastereotopic hydrogens for the sake of this assessment.]
(a)

How many unique ¹H NMR signals would you expect in an NMR spectrum for the following molecules?

(c)

How many sets of equivalent hydrogens are present in the molecule that resulted in this NMR spectrum? [Recall that some signals can be split into multiple peaks—they are still just one signal.]

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Without worrying about the relative location of the signals (i.e., the chemical shift) or the splitting patterns, draw a spectrum of the following molecule. Be sure to label each signal based on the set of equivalent hydrogens to which it corresponds.

Replace Hₐ and H₆ in hexane with a deuterium. What is the relationship between the two products you obtain? Based on this, would you expect the two hydrogens to give one or two signals in the ¹H NMR spectrum?

How many distinct signals would you expect to see in the ¹H NMR spectrum of the following molecules? [Ignore diastereotopic hydrogens for the sake of this assessment.]

(b)

How many distinct signals would you expect to see in the ¹H NMR spectrum of the following molecules? [Ignore diastereotopic hydrogens for the sake of this assessment.]

(c)

How many distinct signals would you expect to see in the ¹H NMR spectrum of the following molecules? [Ignore diastereotopic hydrogens for the sake of this assessment.]

(f)

Radical chlorination, a reaction studied in Chapters 5 and 11, replaces a hydrogen with a chlorine. Assuming there is no regioselectivity (all hydrogens can react equally), how many different chloroalkanes are possible upon reaction of each alkane with one equivalent of Cl₂

(a)

(b)

(c)

(d)