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 B F D E H OH NH2 J Transmitance 0.9 0.8 0.7 0.6 0.5 0.4 0.3 0.2 0.1 0.0 3500 3000 2500 2000 1500 1000 500 30 Wavenumbers (cm-1)

Give the structural formula that is consistent with each 1HNMR spectrum shown below

Assignment 2 1-While cleaning out a laboratory shelf, you have made a mistake in labeling two bottles of phenol and benzene. To identify the molecular structure of the contents of the bottle, samples were submitted for analysis using infrared spectroscopy, based on the IR results, draw the molecular structure of the molecule that would corespond to the spectrum for that compound. Justify vour answer Spectrum A Spectrum B 04 02 3000 2000 Wevenuter kni 1000 2000 Wavene m-1) 3000

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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

Complete the spectroscopy data tables for a compound with molecular formula C6H14. Determine the structure of the compound. Any labile protons, if they exist, will not be present in this particular 1H NMR spectrum.

. Deduce the structure of an unknown compound with the molecular formula of C5H₁2O using the information given by its infrared spectrum. ANSWER A) НО. B) D) Intensity Frequency (peak): (cm): 3300 m EEEEE m m m m m 2900 2800 1465 1450 1375

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?