Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 12.SE, Problem 28AP
Would you expect two enantiomers such as (R)-2-bromobutane and (S)-2-bromobutane to have identical or different IR spectra? Explain.
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Chapter 12 Solutions
Organic Chemistry
Ch. 12.2 - Prob. 1PCh. 12.2 - Two mass spectra are shown in FIGURE 12-8. One...Ch. 12.3 - What are the masses of the charged fragments...Ch. 12.3 - Prob. 4PCh. 12.5 - Prob. 5PCh. 12.5 - Prob. 6PCh. 12.7 - What functional groups might the following...Ch. 12.7 - How might you use IR spectroscopy to distinguish...Ch. 12.8 - Prob. 9PCh. 12.8 - Where might the following compounds have IR...
Ch. 12.8 - Where might the following compound have IR...Ch. 12.SE - Prob. 12VCCh. 12.SE - Show the structures of the fragments you would...Ch. 12.SE - Propose structures for compounds that fit the...Ch. 12.SE - Write molecular formulas for compounds that show...Ch. 12.SE - Camphor, a saturated monoketone from the Asian...Ch. 12.SE - The nitrogen rule of mass spectrometry says that a...Ch. 12.SE - In light of the nitrogen rule mentioned in Problem...Ch. 12.SE - Nicotine is a diamino compound isolated from dried...Ch. 12.SE - The hormone cortisone contains C, H, and O, and...Ch. 12.SE - Halogenated compounds are particularly easy to...Ch. 12.SE - Prob. 22APCh. 12.SE - Propose structures for compounds that fit the...Ch. 12.SE - 2-Methylpentane (C6H14) has the mass spectrum...Ch. 12.SE - Assume that you are in a laboratory carrying out...Ch. 12.SE - What fragments might you expect in the mass...Ch. 12.SE - How might you use IR spectroscopy to distinguish...Ch. 12.SE - Would you expect two enantiomers such as...Ch. 12.SE - Would you expect two diastereomers such as meso-2,...Ch. 12.SE - Propose structures for compounds that meet the...Ch. 12.SE - How could you use infrared spectroscopy to...Ch. 12.SE - Prob. 32APCh. 12.SE - At what approximate positions might the following...Ch. 12.SE - How would you use infrared spectroscopy to...Ch. 12.SE - At what approximate positions might the following...Ch. 12.SE - Assume that you are carrying out the dehydration...Ch. 12.SE - Assume that you are carrying out the base-induced...Ch. 12.SE - Prob. 38APCh. 12.SE - Carvone is an unsaturated ketone responsible for...Ch. 12.SE - Prob. 40APCh. 12.SE - The mass spectrum (a) and the infrared spectrum...Ch. 12.SE - The mass spectrum (a) and the infrared spectrum...Ch. 12.SE - Propose structures for compounds that meet the...Ch. 12.SE - 4-Methyl-2-pentanone and 3-methylpentanal are...Ch. 12.SE - Grignard reagents undergo a general and very...Ch. 12.SE - Ketones undergo a reduction when treated with...Ch. 12.SE - Nitriles, R–=C≡N, undergo a hydrolysis...Ch. 12.SE - The infrared spectrum of the compound with the...Ch. 12.SE - The infrared spectrum of the compound with the...Ch. 12.SE - Prob. 50AP
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- Would you expect two diastereomers such as meso-2, 3-dibromobutane and (2R, 3R)-dibromobutane to have identical or different IR spectra? Explain.arrow_forwardCamphor, a saturated monoketone from the Asian camphor tree, is used among other things as a moth repellent and as a constituent of embalming fluid. If camphor has M+=152.1201 by high-resolution mass spectrometry, what is its molecular formula? How many rings does camphor have?arrow_forwardWhy do aldehydes, esters, and amides all have a strong absorption in the 1630-1780 cm1 region of their IR spectra? A) The bond between H and the sp³-hybridized C in these functional groups vibrates in this energy range. B) Each of these functional groups has at least two resonance structures, and the different vibrations of the resonance structures give off energy in this region. C) The bond between O and the sp²-hybridized C in these functional groups vibrates at a frequency in this energy range. D) Light at this wavenumber causes the average C to O bond length to increase which causes more of this light to be transmitted. E) An electron in the bond of these functional groups gets excited to the * orbital.arrow_forward
- How many stereocentres are present in 2‑bromoethan‑1‑ol?arrow_forwardCyclohex-2-enone has two protons on its carbon-carbon double bond (labeled Ha and Hb) and two protons on the carbon adjacent to the double bond (labeled Hc). (a) If Jab = 11 Hz and Jbc = 4 Hz, sketch the splitting pattern observed for each proton on the sp2 hybridized carbons. (b) Despite the fact that Ha is located adjacent to an electron-withdrawing C=O, its absorption occurs upfield from the signal due to Hb (6.0 vs. 7.0 ppm). Offer an explanation.arrow_forwardCalculate the relative intensity of the mono-isotopic peak for the fullerenes C60 and C84.arrow_forward
- c) The two molecules below both possess a nitro group; however, one of the two nitro groups has a lower N=O stretching frequency its IR spectrum. Which molecule has the lower stretch (i.e. lower wavenumber value), and why? NO2 NO2 versusarrow_forwardShow how to distinguish between 1,3-cyclohexadiene and 1,4-cyclohexadiene by ultra- violet spectroscopy. 1,3-Cyclohexadiene 1,4-Cyclohexadienearrow_forwardA newly discovered chiral compound (BAGO) was analyzed. Four new elements have been discovered (L, R, G and Z) and served as hetero atoms to this chiral compound. The atomic numbers of these elements were in the following order: Z < L< G< R. Additional data for this compound is shown below. Melting point, °C 197.2 Optical Activity Rotation, degrees + 13.9 Density, g/mL 1.56 R BAGO L.arrow_forward
- For the molecules below, assign the stereocenter’s absolute configuration as R or Sarrow_forwardUse compounds D and E shown below to answer this question. What would be the observed rotation of a 4:1 mixture of D:E if pure compound E has a specific rotation of +12°? Show how you arrived at your answer. (Use the back if necessary) CI, Br Br .CI compound D compound Earrow_forwardA molecule with the molecular formula of C3H9N produces the IR spectrum shown below. Draw a structure that best fits this data. 4000 3000 2000 1500 Wavenumbers (cm-¹) 1000 500arrow_forward
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