Bennett & Forster, IR Cards.

Student Handout
IR Inquiry Experiment Objectives to gain more practice recognizing functional groups from structures to gain practice drawing skeletal structures to figure out what IR peaks correspond to what bond types in molecules to learn to use IR spectra to recognize what functional groups are present in a sample

General tips and guidelines: 1. Work in groups of 2-3. Turn in one copy of the worksheet for your group. Make sure all partner names are included. 2. Check out a deck of IR cards 3. Do not write on the IR cards. Alphabetize and return them when you are finished. 4. Ignore any peaks below 1500 cm-1, unless they are particularly prominent. 5. A jagged peak in either direction just below 2400 cm-1 is from an incorrect background subtract of CO2. This peak arises from the constantly changing levels of CO2 in the room. 6. Some peaks may not be marked with numbers but you can estimate what their values are by using the scale on the x-axis. Do not assume that an unmarked peak is an unimportant peak. Some very important peaks are quite subtle (see examples on the next page). 7. All peaks above 1500 cm-1, aside from the CO2 peak, are important. Procedure 1. Sort through the stack of spectra cards, placing all examples of each functional group (FG) into separate piles. There should be 3-4 examples for each functional group. a. alkane only (none of the following FGs present) b. alkene only (none of the following FGs present) c. aromatic only (none of the following FGs present) d. alcohol (this FG and the subsequent ones may include the above FGs also) e. phenol f. carboxylic acid g. ketone h. aldehyde i. ester 2. Place all FG spectra in a vertical array and then try to find characteristics that they all share. When looking for IR peak characteristics you want to consider: a. location: the center of the peak in wavenumbers, cm-1; you may need to estimate some of these, broad peaks should be recorded as a range, e.g., 3500-3200 cm-1 b. intensity: how big/strong a peak is relative to the other peaks, y-axis: tallest peak = very strong, ~75% of tallest peak = strong, ~30-60% of tallest peak = moderate, <25% of tallest peak = weak) c. breadth: how wide a peak issharp <50 cm-1, moderate 50-150 cm-1, broad >150 cm-1) 3. Once you have filled in the worksheet and summarized your findings in your notebook, use this information as a reference to figure out the functional groups in your experimental IR spectra for subsequent labs. 4. Re-alphabetize the cards and return them.

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Bennett & Forster, IR Cards.

Examples:

CO2

CO2

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Bennett & Forster, IR Cards.

Student Worksheet IR Inquiry Experiment Due at the end of lab today Functional Groups: Provide the names and structures from the cards that have the following functional groups. All functional groups have 3-4 examples. alkane only

alkene only

aromatic only

alcohol

phenol

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Bennett & Forster, IR Cards.

carboxylic acid

ketone

aldehyde

ester

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Bennett & Forster, IR Cards.

Characteristics of functional groups in IR spectra: Fill in the following chart with up to three shared peaks that are characteristic of a functional group. Some locations are best reported as ranges. Functional Group e.g., carboxylic acid e.g., aldehyde Alkane Location ~2500-3500 ~2720-2750 Intensity Weak Very weak Breadth Very broad Moderate

Aromatic

Alkene

Alcohol

Phenol

Carboxylic acid

Ketone

Aldehyde

Ester

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Bennett & Forster, IR Cards.

Answer the following questions: 5. What effect does conjugation (alternating pi bonds) have on the location of C=O peaks? First find all examples of the C=O functional groups and then determine which peak they all share. Then compare that peak within a functional group between the conjugated and unconjugated examples to determine the effect of conjugation. Each C=O containing functional group has two conjugated examples and two unconjugated examples. Explain, using specific examples.

6. How can you distinguish an alkene from an aromatic using IR spectra? Explain, using specific examples.

7. How can you distinguish alcohols, phenols, and carboxylic acids from one another using IR spectra? Explain, using specific examples.

8. How can you distinguish an aldehyde from a ketone using IR spectra? Explain, using specific examples.

9. How can you distinguish a carboxylic acid from an ester using IR spectra? Explain, using specific examples.

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