Introduction to using IR and NMR spectroscopy to determine the structure of unknown organic compounds.
Imagine you are a forensic chemist handed a vial of a clear, unknown liquid found at a crime scene. It looks like water, but its molecular structure holds the key to solving the case. How do you 'see' the invisible skeleton of a molecule without a microscope?
Quick Check
If a molecule has a molecular formula of , what is its Degree of Unsaturation?
Answer
1
Infrared (IR) Spectroscopy measures the vibrations of chemical bonds. Different bonds absorb different frequencies of IR light, acting like a 'fingerprint' for functional groups. The most critical regions to memorize are: - **Carbonyl ():** A strong, sharp peak around . - **Hydroxyl ():** A broad, 'tongue-shaped' peak between . - **Carbon-Hydrogen ():** Peaks just below for alkanes. If you see a broad peak at and a sharp peak at , you likely have a carboxylic acid!
Consider Propanal and Propanone. Both have the formula . 1. Both will show a sharp peak at ( group). 2. Propanal (an aldehyde) will show unique stretching peaks near and (the 'aldehyde' peaks). 3. Propanone (a ketone) will lack these specific aldehyde signals, allowing us to distinguish the two structures.
Quick Check
A spectrum shows a broad peak at but no peak at . Is the molecule an alcohol or a ketone?
Answer
Alcohol
**Proton NMR ( NMR)** is the most powerful tool for structure determination. It tells us about the environment of hydrogen atoms. Three things matter: 1. **Chemical Shift ():** Where the peak is. Downfield (higher ppm) means the H is near electronegative atoms like O or N. 2. Integration: The area under the peak, representing the ratio of hydrogens. 3. Splitting (n+1 Rule): A peak will split into peaks, where is the number of neighboring hydrogens on adjacent carbons. A 'quartet' means the H has 3 neighbors.
Identify the NMR pattern for Chloroethane (): 1. The group has 2 neighbors (). According to the rule, , so it appears as a triplet. 2. The group has 3 neighbors (). , so it appears as a quartet. 3. Because the is attached to , its signal will be shifted further 'downfield' (higher ppm) than the signal.
What is the DoU for a molecule with the formula ?
In NMR, if a signal appears as a 'doublet', how many hydrogens are on the adjacent carbon?
An IR peak at that is very broad is characteristic of a Carbon-Carbon triple bond.
Review Tomorrow
In 24 hours, try to sketch the IR and NMR patterns for Ethanol () from memory.
Practice Activity
Find a practice problem set and try to solve for a structure using both IR and NMR data simultaneously—this 'combined' approach is how real chemists work!