1.02 80 1.00 98 0.98 0.96 Transmitance 0.94 92 0.92 0.90 0.88 3750 750 3500 3250 250 3000 000 2750 2750 2500 2250 2000 1750 1500 1500 Wavenumbers (cm-1) 150 1250 1000 000 50 750 Infrared Spectroscopy (IR) is very useful for determining the functional groups present in an organic molecule. For each of the spectra below, complete the following: • Build the molecule in Spartan and describe the motion of the molecule at each key absorption frequency • Identify key absorption frequencies in the spectrum and identify the type of stretch/bend/wag/etc. (i.e. O-H) • Match the spectra from the provided structures • Identify the main functional groups in the molecule OH A OH H B E F H N NH2

See image below

Identify the molecules and why you think it is the molecule.

For the structure and 1H NMR spectrum shown below, match the labeled hydrogen atom groups on the molecule (A-F) with the corresponding signals in the spectrum.

Counterfeit drugs are a common problem in developing regions of the world. Oftentimes, counterfeit pills are made with compounds such as lactose. A lab technician has obtained the IR spectrum shown above for a sample reported to be citalopram, an antidepressant drug. Does the IR spectrum belong to citalopram or lactose? Explain your answer by describing what feature of the IR spectrum confirms your choice and describe what feature is missing from the IR spectrum for the other compound. A. citalopram B. lactose

Based on the spectra you located, does your molecule have a carbonyl? If so, what functional group is it a part of (carboxylic acid, ketone, aldehyde, ester, amide) and what is the frequency (in wavenumbers) of the absorption peak? If not, what is the approximate frequency range for a carbonyl? Does your molecule have either an –O-H or –N-H bond? If so, what functional group is it a part of (carboxylic acid, alcohol, amine, amide) and what is the frequency (in wavenumbers) of the absorption peak? If not, what are the approximate frequency ranges for an –O-H and an –N-H bond? Does your molecule have either an alkyne or nitrile functional group? If so, which functional group is it and what is the frequency (in wavenumbers) of the absorption peak? If not, what is the approximate frequency range for a triple bond?

6) Complete the spectroscopy data tables for a compound with molecular formula C6H12O. Determine the structure of the compound. Any labile protons, if they exist, will not be present in this particular 1H NMR spectrum.

Determine the structure of the compound with the chemical formula shown below, based on the given spectrum. Be sure to show possible fragments for each signal

Based on the spectra provided, draw the structure. Label each unique carbon and hydrogen with the letters A, B, C… for use in assigning NMR peaks. fill in the data table assigning peaks in each spectrum. You should assign: • All 1H NMR peaks • Significant IR peaks above 1600 cm Example of what the table should include (imagine the structure of ethanol is drawn with the CH3 hydrogens labeled as A, the CH2 hydrogens labeled as B, and the OH hydrogen labeled as C) :  hydrogen proton chemical shift  integration splitting pattern couples to.. A 1.2 3 triplet B B 3.7 2 quartet A C 2.6 1 singlet -

Based on the spectra provided, draw the structure. Label each unique carbon and hydrogen with the letters A, B, C… for use in assigning NMR peaks. fill in the data table assigning peaks in each spectrum. You should assign: • All 1H NMR peaks • Significant IR peaks above 1600 cm Example of what the table should include (imagine the structure of ethanol is drawn with the CH3 hydrogens labeled as A, the CH2 hydrogens labeled as B, and the OH hydrogen labeled as C) :  hydrogen proton chemical shift  integration splitting pattern couples to.. A 1.2 3 triplet B B 3.7 2 quartet A C 2.6 1 singlet -