Concept explainers
Interpretation:
The McLafferty rearrangement for the molecular ion of pentanoic acid is to be drawn.
Concept introduction:
These two fragmentation pathways – heterolysis and α-cleavage – are also common to other compound classes that have
In addition to α-cleavage, there is another fragmentation pathway characteristic of carbonyl-containing compounds. A carbonyl-containing compound can undergo a McLafferty rearrangement if an alkyl group attached to the carbonyl carbon possesses a
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- Consider the protons that are in the position ortho- to the carbonyl containing group in the structure shown below. Will these protons be shifted upfield or downfield relative to protons on an unsubstituted benzene ring? A/arrow_forwardConsider 1,1-dimethylcyclobutane. 1. The cycloalkane will exhibit| proton signals in 1H-NMR spectroscopy. 2. The cycloalkane will exhibit carbon signals in 13C-NMR spectroscopy. 3. The cycloalkane contains primary carbons. 4. (Answer by YES or NO). The cycloalkane is a meso compound.arrow_forwardThe following H-NMR spectrum (showing all available signals) is for one of the possible products listed below. This product was obtained from oxidizing one of the alcohols listed below (as possible reactants) using either dichromate (Na2Cr2O7/H2SO4) or DMP. Determine the product, reactant and oxidizing agent following the analysis below. Based on the given H-NMR spectrum, and since there is signals is and the total number of H-NMR the oxidation product must be ÷ Therefore, the oxidizing agent and the reactant must be PPM Possible Reactants OH A Possible Products O I V ОН B ОН VI II ОН C ОН OH III VII OH D OH E IV VIIIarrow_forward
- A. Below is a “Name Reaction” - Clemensen reduction. Describe how the IR spectrum could be used to tell if the reactions had been successful. Provide approximate wave numbers and the corresponding functional groups for the key absorption bands and/or peaks in IR. You might want to describe from two aspects: which peak(s) of what functional group(s) should appear in the IR of the product (that is different from the reactant); which peak(s) of what functional group(s) should disappear in the IR of the product (that is present in the reactant B. For the Clemensen reduction (same reaction), describe how the 1H NMR spectrum could be used to tell if the reactions had been successful. Provide approximate chemical shifts and the integral and the “splitting” of the “unique” in the NMR spectrum. You might want to describe from two aspects: which peak(s) should have a change in chemical shift(s); which peak(s) should have a change in integral; which has a splitting change; which peak(s) will be…arrow_forwardHINT: Integration is just a ratio not the actual number of hydrogens. Q1: The following alcohol undergoes elimination in the presence of concentrated sulfuric acid, but the product shown is not its chief product. Instead, another isomeric six-carbon alkene forms. This product shows a large peak at 20.4 ppm and a smaller one at 123.4 ppm in its proton-decoupled 13C NMR spectrum. Draw the structure of the product and interpret the spectrum. Outline a mechanism for the formation of the product that possesses this spectrum. CH3 CH;-CH-CH-CH2-OH CH3 H,SO, CH;-CH-C=CH2 + H,0arrow_forwardExplain per step. The mass spectra of 1-methoxybutane, 2-methoxybutane, and 2-methoxy-2-methylpropaneare shown. Match the compounds with the spectra.arrow_forward
- Explain the transitions occurring when acetaldehyde (H-CHO) is exposed to EM radiation. Also explain the two Amax obtained in its UV spectrum by giving out the corresponding spectrumarrow_forwardConsider the product below a) Predict the 1H NMR spectrum for this molecule. Predict the multiplicity, integration and relative ppm b) Predict the 13C NMR spectrum and DEPT spectra. Use (+) for positivesignals, (-) for negative signals, and (X) for no signal in the DEPT NMR spectra.arrow_forwardAttached 2nd Reaction was performed in the Synthesis of Dihydrosafrole via Friedel-Crafts Acylation & Reduction Experiment resulting in following IR spectra. Can you analyze it and fill the following table? Are their any impurities found? Peak Position cm-1 Bond Type Functional Grouparrow_forward
- 2) For each of the following pairs of compounds, name one absorption band that can be used to distinguish between them. State what the bond is (bond order, between which 2 atoms), and approximately where it appears in the IR spectrum (in cm ¹). b) HO 1-hexanol OH phenol H₂N 1-butanamine ethyl acetate cyclohexane OH hexanoic acid LOH cyclohexanol NH₂ butanamide diethyl ether cyclohexenearrow_forward4. Look at the structure of the product (provided), 3 hydrogens are labelled (H₁, H₂ and H.). While H₂ may look simple on the ¹H NMR spectrum that you obtained (due to low resolution), it actually has a more complex splitting pattern. Create a tree diagram showing the splitting of H₁. Hint: H₁ is diastereotopic proton, assume JAB > Jac and assume no long range (>3 bond) coupling. AC Hb Ha I Hcarrow_forwardQ4. The following is the 13C NMR spectrum of a highly concentrated solution of dicyclopentadiene obtained in chloroform-d. Despite the high purity of the compound based on ¹H NMR, there is a massive peak observed at 77.2 ppm in this 13C spectrum, which doesn't correspond to any resonances expected for dicyclopentadiene. What is this peak, and why do you not see a corresponding peak for this compound in your ¹H NMR spectrum? 79-751 <-136.22 -132.62 132.27 132.23 135 130 125 120 115 110 105 100 95 90 85 80 75 70 65 60 55 50 45 40 35 30arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning