Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 14.5, Problem 4P
identify the most shielded and least shielded protons in
(a)
(b)
(c)
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Estimate the chemical shifts on the following hydrogens.
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|
OH
(e)
CH₂
CH₂
CH₂CH₂-C-OH
CH₂
H
o CH₂
Without doing the calculation, which member of each pair do you expect to occur at the higher frequency?
(a) C=O or
(b)
(c)
C=C stretching
C=O
C=C
C=O or
C-O stretching
C=O
-0
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C-O stretching
O O
C=C
C=O
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C-H
C-CI
Predict the splitting patterns you would expect for each proton in the following molecules.(a)CHBr2CH3
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Draw structures for compounds that meet the following descriptions:(a) C2H6O; one singlet(b) C3H7Cl; one doublet and one septet(c) C4H8Cl2O; two triplets
Chapter 14 Solutions
Organic Chemistry - Standalone book
Ch. 14.3 - Prob. 1PCh. 14.3 - Prob. 2PCh. 14.4 - The 1H NMR signal for bromoform (CHBr3) appears at...Ch. 14.5 - identify the most shielded and least shielded...Ch. 14.5 - (a) Assign the chemical shifts 1.6, 2.2, and 4.8...Ch. 14.5 - Assign the chemical shifts 1.1, 1.7, 2.0, and 2.3...Ch. 14.5 - Assign the chemical shifts 1.6, 4.0, 7.5, 8.2, and...Ch. 14.6 - The 300-MHz 1H NMR spectrum of 1,4-dimethylbenzene...Ch. 14.6 - Prob. 9PCh. 14.6 - How many signals would you expect to find in the...
Ch. 14.7 - Describe the appearance of the 1H NMR spectrum of...Ch. 14.8 - Describe the appearance of the 1H NMR spectrum of...Ch. 14.11 - Prob. 13PCh. 14.11 - Prob. 14PCh. 14.12 - Hydrogen bonding between the oxygen of dimethyl...Ch. 14.14 - Prob. 16PCh. 14.15 - The 13C NMR spectrum of 1-bromo-3-chloropropane...Ch. 14.15 - Consider carbons x, y, and z in p-methylanisole....Ch. 14.15 - Prob. 19PCh. 14.16 - To which of the compounds of Problem 14.16 does...Ch. 14.18 - DEPT spectra for a compound with the formula...Ch. 14.20 - Vibrational frequencies are sensitive to isotopic...Ch. 14.21 - Prob. 23PCh. 14.22 - Prob. 24PCh. 14.23 - Prob. 25PCh. 14.23 - Which one of the C5H8 isomers shown has its max at...Ch. 14.24 - Knowing what to look for with respect to isotopic...Ch. 14.24 - The base peak appears at m/z105 for one of the...Ch. 14.24 - Mass spectra of 1-bromo-4-propylbenzene and...Ch. 14.25 - Prob. 30PCh. 14 - Each of the following compounds is characterized...Ch. 14 - Deduce the structure of each of the following...Ch. 14 - From among the isomeric compounds of molecular...Ch. 14 - The H1NMR spectrum of fluorene has signals at 3.8...Ch. 14 - Prob. 35PCh. 14 - H1NMR spectra of four isomeric alcohols with...Ch. 14 - Prob. 37PCh. 14 - We noted in Section 14.13 that an NMR spectrum is...Ch. 14 - Identify each of the C4H10O isomers on the basis...Ch. 14 - A compound (C3H7ClO2) exhibited three peaks in its...Ch. 14 - Label nonequivalent carbons in the following...Ch. 14 - Compounds A and B are isomers of molecular formula...Ch. 14 - C13 NMR spectra for four isomeric alkyl bromides...Ch. 14 - Prob. 44PCh. 14 - Prob. 45PCh. 14 - Identify the C3H5Br isomers on the basis of the...Ch. 14 - Prob. 47PCh. 14 - A compound (C8H10O) has the IR and H1NMR spectra...Ch. 14 - Deduce the structure of a compound having the...Ch. 14 - Figure 14.53 presents IR, H1NMR, C13NMR and mass...Ch. 14 - H1NMR, C13NMR, IR, and mass spectra are shown for...Ch. 14 - 1H NMR and IR spectra for a compound with the...Ch. 14 - FriedelCraftsalkylation of benzene with...Ch. 14 - Prob. 54DSPCh. 14 - Prob. 55DSPCh. 14 - Prob. 56DSPCh. 14 - Prob. 57DSPCh. 14 - Prob. 58DSP
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- Cyclohex-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_forward17. Which stretching vibration in this molecule would have the HIGHEST wavenumber (and highest frequency) IR peak? (a) C-C (b) C-O (c) C=O (d) C-H (e) C=C .OH علىarrow_forwardQ2: Choose the correct answer for each of the following: () 1 - In the infrared spectrum of a Compound containing a triple C-C bond, the amplitude oscillation band appears The Stretch) has at: - A) 2700 cm ¹ b) 2100 cm ¹ -1 c) 3100 cm ¹ 2- Stretching frequency of the O=C bond of a compound (3-butene-2-on) is less than the stretching frequency of a compound (2-propanone) a.) hydrogen bonding c) Vibration duplication b) Electronic effects 3- The compound o-hydroxybenzoic acid can be distinguished from the compound m-hydroxybenzoic Acid by infrared spectroscopy based on: a) OH. Group b) group curve oscillation) C-H c) group amplitude oscillation C=Oarrow_forward
- Tell how many peaks are present as a result of spin-spin coupling for each of the hydrogens shown in the structure below.arrow_forwardA compound of formula C20H29NO absorbs 4 molar equivalents of hydrogen. How many rings does it contain?arrow_forward1) Indicate chemically equivalent nuclei (e.g. Ha, Hb, Hc). 2) Estimate the chemical shifts on the following hydrogens. CH₂ OCH₂ O CH₂0 Br CH3-CH-CH₂-CH3 CH3 OH CH3-C-C=C-H CH3 C=C-H O H CH3 Br-C-C-CH3 H Brarrow_forward
- ( which structure fits the best in the given spectra )arrow_forwardNorlutin and Enovid are ketones that suppress ovulation, so they have been used clinically as contraceptives. For which of these compounds would you expect the infrared carbonyl absorption (C=O stretch) to be at a higher frequency? Explain.arrow_forwardDoes C-H absorb more infrared radiaiton than C triple bond C?arrow_forward
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