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)

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 -

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 -

Answer question : B

From the 13C spectrum of a compound, one can assign signals to specific carbon atoms of the compound and determine the number of protons on each of those carbon atoms. Such information in conjunction with the DEPT C-13 chart will allow the appearance of the corresponding DEPT spectrum of the compound to be predicted. There are five signals (I – V) in the 13C spectrum of compound A as shown below. At the exactly same location of each of these five signals, "a peak", "no peak", or "an inverted peak" may appear in the corresponding DEPT-135 spectrum. Predict the DEPT-135 spectrum of compound A by selecting the expected signal appearance at each of these five locations in the DEPT-135 spectrum. - II II IV V in HO A 100 PPM 180 160 140 120 80 60 40 20 v At the location of signal I A. no peak v At the location of signal IIl В. а рeak v At the location of signal IIl C. an inverted peak v At the location of signal IV v A the location of signal V

Consider the following Proton and Carbon NMR spectra for the same compound, and it contains Chlorine. Decide on a structure which is consistent with the spectral data, and 'assign" both spectra as best as you can. "Assign" = draw structure, label (a,b,c etc) and indicate which peaks belong to which type.