Example 3 - Detailed Solution
Hextet at 4.0 δ, 1H. Chemical shift indicates
adjacent to electronegative Cl; choose the yellow –X mosaic
piece. The integral indicates it is a methine, while the
hextet indicates it is next to five neighbor hydrogens: a CH2
and a CH3.
Multiplet at 1.75 δ, 2H. A methylene not next to a functional group. Since it is a multiplet, we cannot tell specifics about the number neighbor hydrogens other than that there are several. Choose a blue methylene mosaic piece, but wait to add the static clings.
Doublet at 1.5 δ, 3H. The chemical shift indicates no adjacent functional group; doublet indicates it is next to one neighbor hydrogen.
Triplet at 1.0 δ, 3H. The chemical shift indicates there is no adjacent functional group; the triplet indicates it is next to two neighbor hydrogens.
Start to put it together. The undetermined CH2
piece is obvious from the neighbor pieces that must bond to it:
Final structure: 2-chlorobutane
