Short Answer 
The synthesis of the compound C14H14O2 involves understanding its aromatic structure and the influence of substituents like methoxy and bromine on distinct hydrogen environments. This analysis leads to a total of 7 unique proton NMR signals, consisting of 4 from different aromatic positions, 1 from the methoxy group, 1 from the methyl group, and 1 from the hydroxyl group.
Step 1: Understand the Compound Structure
Begin by analyzing the compound structure of C14H14O2, which is synthesized from 1-bromo-4-methoxybenzene and m-cresol. This involves recognizing that the compound forms a connected aromatic framework as a result of the coupling reaction. Understanding the structure is crucial because it influences the number of distinct hydrogen environments present in the NMR spectrum.
Step 2: Identify Hydrogen Environments
Next, focus on identifying the unique hydrogen environments in the compound. This includes:
- Aromatic Hydrogens: Both starting compounds possess aromatic rings, leading to multiple distinct proton environments.
- Influence of Substituents: The substitution patterns of heteroatoms like methoxy (electron-donating) and bromine (electron-withdrawing) affect the chemical shifts, creating different signals for each hydrogen attached to the aromatic system.
Step 3: Count and Summarize Distinct Signals
Finally, count the distinct signals expected in the NMR spectrum based on the environments identified.
- 4 distinct signals from different aromatic positions due to varied hydrogen environments.
- 1 signal from the methoxy group (-OCH3).
- 1 signal from the methyl group (-CH3) attached to the m-cresol.
- 1 signal from the hydroxyl group (-OH).