Ch. 15 - Analytical Techniques: IR, NMR, Mass SpectSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins

Practice: Draw the approximate positions that the following compound might show in its 1H NMR absorptions?

Practice: Draw the approximate positions that the following compound might show in its 1H NMR absorptions?

Additional Problems
How would you distinguish between these compounds via  1H NMR?
Which 1H NMR spectrum is consistent with that of ethyl methyl sulfide, CH 3CH2SCH3? •
Which compound belongs to following 1H NMR?
Which structure is consistent with this  1H NMR spectrum?
Which structure is consistent with this  1H NMR spectrum?
Which structure is consistent with this  1H NMR spectrum?
The molecular formula, IR & NMR are provided for the following unknown compounds. For each problem, provide the structural information from the IR & NMR and propose a structure for the unknown.  
There are four constitutional isomers of dichloropropane. The NMRs of 3 of these are shown below. Match each isomer with its NMR and provide an interpretation of each spectrum. (i.e. draw the structure on the NMR and  label protons , with their splitting.)
 Predict the structure of the compound that gives rise to the following  1H NMR spectra: Molecular Formula: C4H8O  
Predict the structure of the compound that gives rise to the following  1H NMR spectra: Molecular Formula: C9H11Cl  
Sketch the 1H NMR spectrum and assign the peaks in each of the following compound.  
Which of the following aromatic compounds most likely generated the accompanying 1H-NMR spectrum?
Predict the structure of the compound that gives rise to the following  1H NMR spectra. Molecular Formula C5H9CIO
Which structure is consistent with the following 1H NMR spectrum? a ethyl acetate b 2-propanone c 3,3-dimethyl-2-pentanone d ethyl 2,2-dimethylpropionate e none of theses
A compound C5H10O gave the following spectral data: 1H NMR spectrum                              IR spectrum doublet, δ 1.10                                  strong peak singlet, δ 2.10                                   near 1720 cm    -1 septet, δ 2.50 Which is a reasonable structure for the compound?
A compound C4H9Br gave the following 1HNMR spectrum: triplet, δ 1.0 (3H); doublet, δ 1.7; multiplet, δ 1.8; multiplet, δ 4.1 (1H) Which is a reasonable structure for the compound? A) CHCH2CHBrCH3 B) CH3CH2CH2CH2Br C) (CH3)2CHCH2Br D) (CH3)3CBr
Answer the following questions about product identity based on IR & NMR spectroscopy.
What  1H NMR spectral data is expected for the compound shown? a. 3.8 (1H, septet), 2.1 (3H, s), 1.0 (6H, d)                        c 3.3 (3H, s), 2.6 (3H, septet), 1.0 (6H, d) b. 3.8 (1H, septet), 9.3 (3H, s), 1.0 (6H, d)                        d 2.6 (1H, septet), 2.1 (3H, s), 1.0 (6H, d)
The 1H NMR spectra for the following molecule is provided. In the fragments box below, propose which fragments are elucidated by the spectra and use arrows to match those fragments to each signal on the spectra, respectively. 
Which of the compound listed below has a structure consistent with the following   1H NMR spectrum? a. 4-bromoanisole b. Anisole c. 4-bromoaniline d. None of them e. Phenol
An unknown compound W has the molecular formula C 4H8O2. Based on the following 1H NMR spectrum, what is the structure of compound W?   
Predict the 1H NMR of compound A in CDCl3. Show clearly the relative intensity, chemical shift and splitting pattern of each peak. Indicate in the spectrum, using the appropriate number shown for the carbons, where the protons resonate. Note: add as reference peaks the TMS and residual CHCl3.
The reaction between compound 1 and NaOCHMe2 in Me2CHOH as a solvent produces a mixture of two products 2 and 3, all with identical molecular formula and with a relative yield of 50% and 50% respectively. The 1NMR of these compounds with relative integrations of signals is shown below. What are the structures of compounds 2 and 3? b. With what reagent and solvent would you treat compound 1 if you want to obtain higher yield of compound 2? Explain your answer with 1-2 sentences c.  With what reagent and solvent would you treat compound 1 if you want to obtain higher yield of compound 3? Explain your answer with 1-2 sentences d.  Based on the data above, what product(s) and in what relative ratio(s) would you obtain by treating compound 4 ((t-But)2CHCH(Br)CH3) with NaOCHMe2 in Me2CHOH as the solvent under the same conditions as above? Explain your answer with 1-2 sentences.
The 1H NMR spectrum of a compound with formula C 7H14O gives two signals. Which of these structures is a possible one for this compound? A) 2-Heptanone B) 3-Heptanone C) 2,4-Dimethyl-3-pentanone D) 2,2-Dimethyl-3-pentanone E) Two of the above
The 1H NMR spectrum of Compound C (C10H14O) is shown below. Draw the structure of the compound C in the box provided. Mark down your thought process. Even if the final structure is wrong, partial credit might be given if your analysis and approach make sense.
Compound A can be converted into compound B by the reaction shown below. Considering the two 1H NMR spectra provided, draw the structures corresponding to compounds Aand B in the box.
Which of the following atoms has a quantum spin number? A) 2H B) 12C C) 15N D) 16O
Circle the molecule that corresponds to the NMR spectrum shown below.
Assign the 1H NMR to the appropriate structure out of the following possibilities. Choose the letter corresponding to the appropriate molecule  for this question. 
Circle the molecule that corresponds to the NMR spectrum shown below.
Assign the 1H NMR to the appropriate structure out of the following possibilities. Choose the letter corresponding to the appropriate molecule  for this question. 
Which compound  shows  three signals (all singlets) in 1H NMR spectrum?
Assign the 1H NMR to the appropriate structure out of the following possibilities. Choose the letter corresponding to the appropriate molecule  for this question. 
Sketch an approximation of the 1H NMR spectrum for the following molecule:
Sketch what you believe the 1H NMR spectrum of compound X would look like:
Sketch the 1H NMR spectrum of methyl propionate. Match the peaks with the protons in the structure. Mark the splitting patterns (e.g. singlet, doublet, triplet, or quartet) and number of protons for each signal (e.g. 1H, 2H, or 3H).
In the boxes provided, place that letter (A, B, C, etc.) that corresponds to the signals in the spectrum provided below.