CHEM PRINCIPLES LL W/ACHIEVE ONE-SEM
7th Edition
ISBN: 9781319420994
Author: ATKINS
Publisher: MAC HIGHER
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Chapter 11, Problem 11.38E
Interpretation Introduction
Interpretation:
The difference in
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Provide an explanation without using the pka values :
Why is phenol stronger acid than butanoic acid?
11.27: Tell which is the stronger base and why?
Aniline or p-cyanoaniline
b) aniline or diphenylamine
WH₂
|ال
11.30: Place the following substances, which have nearly identical
formula weights, in order of increasing boiling point?
1-aminobutane, 1-butanol, methyl propyl ether, pentane
Naming dicarboxylic acids and their pKa values:
Chapter 11 Solutions
CHEM PRINCIPLES LL W/ACHIEVE ONE-SEM
Ch. 11 - Prob. 11A.1ASTCh. 11 - Prob. 11A.1BSTCh. 11 - Prob. 11A.2ASTCh. 11 - Prob. 11A.2BSTCh. 11 - Prob. 11A.3ASTCh. 11 - Prob. 11A.3BSTCh. 11 - Prob. 11A.4ASTCh. 11 - Prob. 11A.4BSTCh. 11 - Prob. 11A.5ASTCh. 11 - Prob. 11A.5BST
Ch. 11 - Prob. 11A.6ASTCh. 11 - Prob. 11A.6BSTCh. 11 - Prob. 11A.1ECh. 11 - Prob. 11A.2ECh. 11 - Prob. 11A.3ECh. 11 - Prob. 11A.4ECh. 11 - Prob. 11A.5ECh. 11 - Prob. 11A.6ECh. 11 - Prob. 11A.7ECh. 11 - Prob. 11A.8ECh. 11 - Prob. 11A.9ECh. 11 - Prob. 11A.10ECh. 11 - Prob. 11A.11ECh. 11 - Prob. 11A.12ECh. 11 - Prob. 11A.13ECh. 11 - Prob. 11A.14ECh. 11 - Prob. 11A.15ECh. 11 - Prob. 11A.16ECh. 11 - Prob. 11A.17ECh. 11 - Prob. 11A.18ECh. 11 - Prob. 11A.19ECh. 11 - Prob. 11A.20ECh. 11 - Prob. 11A.21ECh. 11 - Prob. 11A.22ECh. 11 - Prob. 11A.23ECh. 11 - Prob. 11A.24ECh. 11 - Prob. 11A.25ECh. 11 - Prob. 11A.26ECh. 11 - Prob. 11A.27ECh. 11 - Prob. 11A.28ECh. 11 - Prob. 11B.1ASTCh. 11 - Prob. 11B.1BSTCh. 11 - Prob. 11B.1ECh. 11 - Prob. 11B.3ECh. 11 - Prob. 11B.4ECh. 11 - Prob. 11B.5ECh. 11 - Prob. 11B.6ECh. 11 - Prob. 11B.7ECh. 11 - Prob. 11B.8ECh. 11 - Prob. 11C.1ASTCh. 11 - Prob. 11C.1BSTCh. 11 - Prob. 11C.1ECh. 11 - Prob. 11C.2ECh. 11 - Prob. 11C.3ECh. 11 - Prob. 11C.4ECh. 11 - Prob. 11C.5ECh. 11 - Prob. 11C.6ECh. 11 - Prob. 11C.7ECh. 11 - Prob. 11C.8ECh. 11 - Prob. 11C.9ECh. 11 - Prob. 11C.10ECh. 11 - Prob. 11C.11ECh. 11 - Prob. 11C.12ECh. 11 - Prob. 11C.13ECh. 11 - Prob. 11C.14ECh. 11 - Prob. 11D.1ASTCh. 11 - Prob. 11D.1BSTCh. 11 - Prob. 11D.2ASTCh. 11 - Prob. 11D.2BSTCh. 11 - Prob. 11D.3ASTCh. 11 - Prob. 11D.3BSTCh. 11 - Prob. 11D.1ECh. 11 - Prob. 11D.2ECh. 11 - Prob. 11D.3ECh. 11 - Prob. 11D.4ECh. 11 - Prob. 11D.5ECh. 11 - Prob. 11D.6ECh. 11 - Prob. 11D.7ECh. 11 - Prob. 11D.8ECh. 11 - Prob. 11D.9ECh. 11 - Prob. 11D.10ECh. 11 - Prob. 11D.11ECh. 11 - Prob. 11D.12ECh. 11 - Prob. 11D.13ECh. 11 - Prob. 11D.14ECh. 11 - Prob. 11D.15ECh. 11 - Prob. 11D.16ECh. 11 - Prob. 11D.17ECh. 11 - Prob. 11D.18ECh. 11 - Prob. 11D.19ECh. 11 - Prob. 11D.20ECh. 11 - Prob. 11D.21ECh. 11 - Prob. 11D.22ECh. 11 - Prob. 11D.23ECh. 11 - Prob. 11D.24ECh. 11 - Prob. 11D.25ECh. 11 - Prob. 11D.26ECh. 11 - Prob. 11D.27ECh. 11 - Prob. 11D.28ECh. 11 - Prob. 11D.29ECh. 11 - Prob. 11D.30ECh. 11 - Prob. 11D.31ECh. 11 - Prob. 11D.32ECh. 11 - Prob. 11D.33ECh. 11 - Prob. 11D.34ECh. 11 - Prob. 11D.35ECh. 11 - Prob. 11D.36ECh. 11 - Prob. 11E.1ASTCh. 11 - Prob. 11E.1BSTCh. 11 - Prob. 11E.2ASTCh. 11 - Prob. 11E.2BSTCh. 11 - Prob. 11E.1ECh. 11 - Prob. 11E.3ECh. 11 - Prob. 11E.4ECh. 11 - Prob. 11E.5ECh. 11 - Prob. 11E.7ECh. 11 - Prob. 11E.8ECh. 11 - Prob. 11E.9ECh. 11 - Prob. 11E.10ECh. 11 - Prob. 11E.11ECh. 11 - Prob. 11E.12ECh. 11 - Prob. 11E.13ECh. 11 - Prob. 11E.14ECh. 11 - Prob. 11E.15ECh. 11 - Prob. 11E.16ECh. 11 - Prob. 11E.17ECh. 11 - Prob. 11E.18ECh. 11 - Prob. 11E.19ECh. 11 - Prob. 11E.20ECh. 11 - Prob. 11E.21ECh. 11 - Prob. 11E.22ECh. 11 - Prob. 11E.23ECh. 11 - Prob. 11E.24ECh. 11 - Prob. 11E.25ECh. 11 - Prob. 11E.26ECh. 11 - Prob. 11E.27ECh. 11 - Prob. 11E.28ECh. 11 - Prob. 11.1ECh. 11 - Prob. 11.2ECh. 11 - Prob. 11.3ECh. 11 - Prob. 11.4ECh. 11 - Prob. 11.5ECh. 11 - Prob. 11.6ECh. 11 - Prob. 11.7ECh. 11 - Prob. 11.8ECh. 11 - Prob. 11.9ECh. 11 - Prob. 11.10ECh. 11 - Prob. 11.11ECh. 11 - Prob. 11.12ECh. 11 - Prob. 11.13ECh. 11 - Prob. 11.14ECh. 11 - Prob. 11.15ECh. 11 - Prob. 11.16ECh. 11 - Prob. 11.17ECh. 11 - Prob. 11.18ECh. 11 - Prob. 11.19ECh. 11 - Prob. 11.20ECh. 11 - Prob. 11.21ECh. 11 - Prob. 11.23ECh. 11 - Prob. 11.24ECh. 11 - Prob. 11.25ECh. 11 - Prob. 11.26ECh. 11 - Prob. 11.27ECh. 11 - Prob. 11.28ECh. 11 - Prob. 11.29ECh. 11 - Prob. 11.30ECh. 11 - Prob. 11.31ECh. 11 - Prob. 11.32ECh. 11 - Prob. 11.33ECh. 11 - Prob. 11.34ECh. 11 - Prob. 11.35ECh. 11 - Prob. 11.36ECh. 11 - Prob. 11.37ECh. 11 - Prob. 11.38ECh. 11 - Prob. 11.41ECh. 11 - Prob. 11.42ECh. 11 - Prob. 11.43ECh. 11 - Prob. 11.44ECh. 11 - Prob. 11.45ECh. 11 - Prob. 11.47ECh. 11 - Prob. 11.49ECh. 11 - Prob. 11.50ECh. 11 - Prob. 11.51ECh. 11 - Prob. 11.52ECh. 11 - Prob. 11.53ECh. 11 - Prob. 11.54ECh. 11 - Prob. 11.55ECh. 11 - Prob. 11.56ECh. 11 - Prob. 11.57E
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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_forwardTwo pKa values are reported for malonic acid, a compound with two COOH groups. Explain why one pKa is lower and one pKa is higher than the pKa of acetic acid (CH3COOH, pKa = 4.8).arrow_forwardThe pKa of phenol is 10.0 and the pKa of para-nitrophenol is 7.2. Given this information, one knows that The conjugate base of para-nitrophenol must be less stable than the conjugate base of phenol The conjugate acid of para-nitrophenol must be more stable than the conjugate base of phenol The conjugate base of para-nitrophenol must be more stable than the conjugate base of phenol Both acids are basesarrow_forward
- Given that C6H11COOH has a pKa = 4.8 and C6H11N+H3 has a pKa = 10.7, (a) What pH would you make the water layer to cause the carboxylic acid to dissolve in the water layer and the amine to dissolve in the ether layer? (b) What pH would you make the water layer to cause the carboxylic acid to dissolve in the ether layer and the amine to dissolve in the water layer?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_forward4-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.arrow_forward
- Using pKa Values to Determine Relative Acidity and Basicity Rank the following compounds in order of increasing acidity, and then rank their conjugate bases in order of increasing basicity.arrow_forward4) Multistriatin, one of the pheremones of the elm bark beetle, is a volatile compound released by a virgin female beetle when she has found a good food source - an elm tree. Male beetles, which carry the Dutch elm disease fungus, are attracted by the pheromone; the tree becomes infected with the fungus and soon dies. Multistriatin is used to trap the beetles, but the amount in beetles is so miniscule that the compound must be synthesized. The following synthesis of multistriatin uses only chemistry that we have seen in Chem 348. HO. НО Br type O type. H type H H CH3 H HO HO type O H CH3 "Η OH type H hint: anhydrous cond CH3 H = H type type HO CH3 H H type CH 3 H Multistriatin Multistriatinarrow_forward(a) Explain how NaBH, in CH;OH can reduce hemiacetal A to 1,4-butanediol (HOCH,CH,CH,CH,OH). (b) What product is formed when A is treated with Ph;P=CHCH,CH(CH),? (c) The drug isotretinoin is formed by reaction of X and Y. What is the structure of isotretinoin? Although isotretinoin (trade name Accutane or Roaccutane) is used for the treatment of severe acne, it is dispensed under strict controls because it also causes birth defects. PPha NaOCH,CH3 HO- isotretinoin HO A Br X Yarrow_forward
- Aspirin is the common name for the compound acetylsalicylic acid, widely used as a fever reducer and as a pain killer. Salicylic acid, whose name comes from Salix, the willow family of plants, was derived from willow bark extracts. In folk medicine, willow bark teas were used as headache remedies and other tonics. Nowadays, salicylic acid is administered in the form of aspirin which is less irritating to the stomach than salicylic acid. To prepare aspirin, salicylic acid is reacted with an excess of acetic anhydride. A small amount of a strong acid is used as a catalyst which speeds up the reaction. In this experiment, phosphoric acid will be used as the catalyst. The excess acetic acid will be quenched with the addition of water. The aspirin product is not very soluble in water so the aspirin product will precipitate when water is added. The synthesis reaction of aspirin is shown below: Actic anhydride 5 ml. Acetic acid Salicylic acid 28 Acetylsalicylie acid Procedure 1) Mix salicylic…arrow_forwardCarboxylic acids are acidic enough to dissolve in both 10% NaOH and NaHCO3. Phenols, ArOH, are weak acids and most phenols will not dissolve in 10% NaHCO3. How would you separate a mixture of a carboxylic acid (RCOOH), an amine (RNH2), a phenol (ArOH) and a hydrocarbon (RH) using chemically active extraction? Draw a flow chart to illustrate your separation. Show each species in the aqueous and organic layers.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_forward
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