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 14.12, Problem 15P
Hydrogen bonding between the oxygen of dimethyl sulfoxide (DMSO) and the proton of an
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Phenol (hydroxybenzene) behaves as a weak acid.
a) Write out the equilibrium equation for its partial dissociation in water.
b) Write out the expression for the acid dissociation constant, Ka.
d) Draw the conjugate base of phenol and show how it is stabilised by resonance.
e) Compare and explain the acidity of phenol (p = 9.9) with that of:
cyclohexanol (pk = 16.0)
3-fluorophenol (pK₁ = 9.3)
4-acetylphenol (pK, = 8.1)
Draw the condensed structure of the organic molecule that produces sodium propanoate when reacted with NaOH.
Correct each molecule in the drawing area below so that it has the structure it would have if it were dissolved in a 0.1 M aqueous solution of NaOH.
If there are no changes to be made, check the No changes box under the drawing area.
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HO–CH,—CH, NH
HO—CH,
OH
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4-Methylphenol is more acidic than ethanol (pKa 10.36 vs 16.0) , even though both contain an OH group and a methyl group. Draw the structures of the anions formed from loss of the alcoholic protons from both compounds. Use resonance to explain the difference in their respective acidities.
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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- 16-17 Propylamine (bp 48°C), ethylmethylamine (bp 37°C), and trimethylamine (bp 3°C) are constitutional isomers with the molecular formula C3HgN. Account for the fact that trimethylamine has the lowest boiling point of the three and propylamine has the highest.arrow_forward17-27 Pentane, 1-butanol, and butanal all have approximately the same molecular weights but different boiling points. Arrange them in order of increasing boiling point. Explain the basis for your ranking.arrow_forwardMany multi-step organic reaction mechanisms involve proton transfer steps. For example, the first step of Fischer esterification of carboxylic acids(as shown with acedic acid) is activation of the acid by protonation. Based on your understanding of which reaction pathway is more favorable, explain why using chemical structures.arrow_forward
- Which type of compound typically give 3 peaks ("bands") between approx. 1500-1600 cm in an IR spectrum? Select one: Carbonates Esters Alkaloids Aromatic compoundsarrow_forward10. Choose the major organic product of the reaction. A | В II IV Br Br Br Br Br Br2 Br Br 100°C Br IV =arrow_forwardShow the reaction and equilibrium expression for the basic dissociation of trimethylamine. Given that the Ka = 1.58 x 10-10 for trimethyl ammonium ion, use this to calculate the equilibrium constant for the basic dissociation of trimethyl amine. If the concentration of trimethylamine is 0.10 M, what is the pH of the solution?arrow_forward
- Arrange the following substances in order of increasing pK₁. I ||| < || < | | < ||| < || O || < | < ||| ○ I < || < ||| ||| < | < || ○ || < ||| < | OH II OH III Û OHarrow_forwardAn IR spectrum, a 13C NMR spectrum, and a 1H NMR spectrum were obtained for an unknown structure with a molecular formula of C8H18O. Draw the structure of this compound.arrow_forwardSuggest a possible structure for Compound X.arrow_forward
- Fill in the missing information. OH Н+ НО OH m-CPBA ОН Br H2 Pd/C 1. NaBH4 2. H,0+arrow_forward4. The pk, of vanillin is about 9, which is much more acidic than a normal alcohol. Draw a reaction showing the deprotonation of vanillin with NaOH, and then draw six resonance structures of the conjugate base. Draw the hybrid structure and clearly indicate how the negative charge is distributed in the compound.arrow_forwardO—CH,CH,CH HBrarrow_forward
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