Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Question
Chapter 12.SE, Problem 40AP
Interpretation Introduction
Interpretation:
The nature of the
Concept introduction:
Spectroscopy:
It is study of the interaction of matter and
IR frequency (cm-1):
It is the number of wave crests that pass by a given point in one second frequency has units of hertz (Hz).
Stretch vibrations:
It is a vibration occurring along the line of the bond a stretching vibration changes the bond length.
Bending vibrations:
It is a vibration that does not occur along the line of the bond, bending vibration changes the bond angle.
Given information:
The intense absorption at 1690cm-1 for Carvone.
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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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- Describe two significant differences between the infrared spectra of ethyl alcohol(CH3CH2OH) and ethylene (CH=CH).arrow_forwardThe functional groups in an organic compound can frequently be deduced from its infrared absorption spectrum. A compound containing no nitrogen exhibits strong, broad absorption across the 2500-3300 cm-1 region, accompanied by 2200 (w) and 1715 (s) cm-1bands.Relative absorption intensity: (s)=strong, (m)=medium, (w)=weak. What functional class(es) does the compound belong to? List only classes for which evidence is given here. Attach no significance to evidence not cited explicitly.Do not over-interpret exact absorption band positions. None of your inferences should depend on small differences like 10 to 20 cm-1. The functional class(es) of this compound is(are)fill in the blank 1.(Enter letters from the table below, in any order, with no spaces or commas.) a. alkane (List only if no other functional class applies.) b. alkene h. amine c. terminal alkyne i. aldehyde or ketone d. internal alkyne j. carboxylic acid e. arene k. ester f. alcohol l. nitrile g. etherarrow_forwardSaturated aldehyde Aromatic aldehyde At what position would you expect to observe IR absorption for the carbonyl groups in the following molecules? Infrared Absorptions of Some Aldehydes and Ketones. Carbonyl type Absorption cm-1 1730 1705 Example CH3CHO PhCHO a,ẞ-Unsaturated H2C=CHCHO 1705 aldehyde Saturated ketone CH3 COCH3 1715 Cyclohexanone 1715 Cyclopentanone 1750 Cyclobutanone Aromatic ketone 1785 PhCOCH3 a,ẞ-Unsaturated ketone H2C=CHCOCH3 1685 1690 Molecule #1: Molecule #2: CHO CHO CH3 cm-1 cm -1arrow_forward
- Hw.230.arrow_forwardN-H bonds in ammonia NH_3NH3 produce an IR absorbance at 3335 cm^-1. P-H bonds in phosphine PH_3PH3 produce an IR absorbance at 2327 ccm−1. Explain the difference in a single sentencearrow_forwardThe max peak in the UV-VIS absorption spectrum of acetone appears at 279nm when hexane is used as a solvent, but shifts to 262nm when water is used as solvent. Explain.arrow_forward
- You measured the carbon-carbon bond lengths of four different compounds in Experiment 8 (Molecular Modeling and IR spectroscopy). Which of the following compounds has the shortest average C-C bond length? Benzene Cyclohexene Cyclohexane O Cyclohexadiene Which of the following statement(s) is(are) true? Select all that apply: When two atoms are bonded together, the distance between atoms is the same all the time. In the IR spectrum, carbonyl groups (C=O) have strong sharp peaks ranging from 1700 cm 1 to 1750 cm-1. When a molecule absorbs an IR radiation, electrons are excited within the molecule and each absorbed electron creates a band in the molecules IR spectrum. IR spectroscopy is useful in confirming the structure of the analyzed compound. Molecule N2 does not absorb IR radiationarrow_forwardN-H bonds absorb IR radiation at very similar frequencies as O-H (alcohol) bonds. Oftentimes, they are not quite as large. Why?arrow_forwardThe functional groups in an organic compound can frequently be deduced from its infrared absorption spectrum. A compound containing C, H, and O exhibits broad absorption at 3450 cm-1 (m) and an intense band at 1725, plus a band at 1100 cm-1 (m).Relative absorption intensity: (s)=strong, (m)=medium, (w)=weak. What functional class(es) does the compound belong to? List only classes for which evidence is given here. Attach no significance to evidence not cited explicitly.Do not over-interpret exact absorption band positions. None of your inferences should depend on small differences like 10 to 20 cm-1. The functional class(es) of this compound is(are)fill in the blank 1.(Enter letters from the table below, in any order, with no spaces or commas.) a. alkane (List only if no other functional class applies.) b. alkene h. amine c. terminal alkyne i. aldehyde or ketone d. internal alkyne j. carboxylic acid e. arene k. ester f. alcohol l. nitrile g. etherarrow_forward
- The molecule β-carotene has λmax 450 nm, and ɛ = 15,000 m2 mol-1. Calculate the absorption (A) expected for a solution in which 0.1 mg has been dissolved in 10 ml of water (given: the molecular weight of β-carotene, C40H56, as 536) with a path length of 1 cm. 2.8 0.28 2.8 x 10-4 0.028arrow_forwardConsider the marked absorptions and assign the specific type of vibration as: straight C-H sp3, spe2, sp or aldehyde; O-H from alcohol, acid carb; N-H of amine or amide; C = O of aldehyde, ketone, ester, amide or anhydride; C = C aromatic or C = C alkene; C-O of acid, ester, arom ether, aliph ether, primary, secondary or tertiary alcohol; alkene fingerprints (trans, cis, mono sub or 1,1-disust); benzene (mono, o, m, p); scissor bending of CH3, or CH2.arrow_forwardThe infiared spectrum of a compound contains a strong absorption at 1702 cm-1. The mass spectrum of the compound is shown below. What is the structure of the compound? 100 10 50 70 m/z 80 100 110 120 Relative Intensityarrow_forward
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