Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 3, Problem 3.53P
Interpretation Introduction
Interpretation: The more soluble compound among diethyl ether and tetrahydrofuran is to be predicted. An explanation corresponding to the more soluble compound is to be stated.
Concept introduction: According to the concept of solubility, it is mentioned that like dissolves like. Generally, polar compound can only be dissolved in polar solvents and non-polar or weakly polar compounds can only be dissolved in non-polar solvents or weakly polar solvents.
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Students have asked these similar questions
Propanol is very soluble in water, but ethanethiol and chloroethane are only slightly soluble. Explain.
Although diethyl ether and tetrahydrofuran are both four-carbon ethers, one compound is much more water soluble than the other. Predict which compound has higher water solubility and offer an explanation ?
Why are the boiling points of ethers similar to those of alkanes instead of alcohols?
a)
Both ether molecules and alkane molecules are polar, whereas alcohol molecules are nonpolar.
b)
Hydrogen bonding between ether molecules is strong and this property is similar to that of alkanes. However, hydrogen bonding is weaker in alcohols than it is in both ethers and alkanes.
c)
Although ether molecules are polar, they cannot form hydrogen bonds with other ether molecules. Similarly, alkane molecules do not form hydrogen bonds, whereas there is hydrogen bonding in alcohols.
d)
None of these are correct explanations.
Chapter 3 Solutions
Organic Chemistry
Ch. 3 - Prob. 3.1PCh. 3 - Prob. 3.2PCh. 3 - Draw the structure of a compound fitting each...Ch. 3 - Draw structures that fit each description and name...Ch. 3 - What types of intermolecular forces are present in...Ch. 3 - Prob. 3.6PCh. 3 - Explain why the boiling point of propanamide, is...Ch. 3 - Predict which compound in each pair has the higher...Ch. 3 - Prob. 3.9PCh. 3 - Prob. 3.10P
Ch. 3 - a Label the hydrophobic and hydrophilic portions...Ch. 3 - Prob. 3.12PCh. 3 - Prob. 3.13PCh. 3 - Prob. 3.14PCh. 3 - Prob. 3.15PCh. 3 - Nonactin and valinomycin each contain only two...Ch. 3 - Prob. 3.17PCh. 3 - Problem 3.26 Label the electrophilic and...Ch. 3 - Problem 3.27 Considering only electron density,...Ch. 3 - The fact that sweet-tasting carbohydrates like...Ch. 3 - 3.29
Identify the functional groups in the...Ch. 3 - Prob. 3.22PCh. 3 - 3.32 Identify the functional groups in each...Ch. 3 - Draw the seven constitutional isomers having...Ch. 3 - 3.33 Identify each functional group located in the...Ch. 3 - Draw seven constitutional isomers with molecular...Ch. 3 - Prob. 3.27PCh. 3 - Prob. 3.28PCh. 3 - Prob. 3.29PCh. 3 - Intramolecular force of attraction are often...Ch. 3 - 3.40 (a) Draw four compounds with molecular...Ch. 3 - Prob. 3.32PCh. 3 - Explain why CH3CH2NHCH3 has higher boiling point...Ch. 3 - Prob. 3.34PCh. 3 - Prob. 3.35PCh. 3 - Explain the observed trend in the melting points...Ch. 3 - Prob. 3.37PCh. 3 - Prob. 3.38PCh. 3 - Prob. 3.39PCh. 3 - 3.48 Explain why diethylether and have similar...Ch. 3 - Prob. 3.41PCh. 3 - 3.50 Predict the solubility of each of the...Ch. 3 - Prob. 3.43PCh. 3 - Prob. 3.44PCh. 3 - THC is the active component in marijuana, and...Ch. 3 - Prob. 3.46PCh. 3 - Prob. 3.47PCh. 3 - Prob. 3.48PCh. 3 - Label the electrophilic and nucleophilic sites in...Ch. 3 - By using only electron density arguments,...Ch. 3 - Prob. 3.51PCh. 3 - Prob. 3.52PCh. 3 - Prob. 3.53PCh. 3 - Prob. 3.54PCh. 3 - Prob. 3.55PCh. 3 - Recall from section 1.10B that there is restricted...
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- Explain the solubility of alcohols in water and in n-hexane.arrow_forwardDifferentiate petroleum ether and sulfuric ether in terms of solubility in waterarrow_forwardWhich of the following best describes the solubility of aldehydes and ketones? A) They are all soluble in water and organic solvents. B) They are water soluble but not soluble in organic solvents. C) They are soluble in all organic solvents but only soluble in water for low molecular mass species. D) They are all soluble in water but only soluble in organic solvents for low molecular mass species.arrow_forward
- From their structures, explain why 1-hexanol is more soluble in ether than water and why boric acid is more soluble in water than ether.arrow_forwardA) The boiling points of aldehydes and ketones is higher than that of alkanes but lower than that of alcohols. Discuss these differences in boiling points for these compounds. B) Acetone is a ketone and a solvent used to remove nail polish. If acetone cannot hydrogen bond with each other, why is it soluble in water?arrow_forwardWhich is NOT a physical property of alcohols or phenols? O Phenols are generally only slightly soluble in water. O The hydroxyl group of an alcohol is nonpolar. The solubilities of normal primary alcohols in water decrease with increasing molecular weight. Boiling points of normal primary alcohols increase with increasing molecular weight.arrow_forward
- why do some ethers with the same molecular formulas as their respective alcohols have a lower boiling point?arrow_forwardWrite a generalized statement regarding the solubility of hydrocarbons in a polar solvent (water) and a less polar solvent (dicloromethane) .What conclusion can you make regarding the polarity of hydrocarbons?arrow_forwardExplain why these compounds (1-propanol, ethylene glycol, and ethanethiol) experience different intermolecular forces based on their molecular structure.arrow_forward
- Which of the two has a higher boiling point: Propanol or Pentanol?arrow_forwardThe C-O bond is much shorter in phenol than in ethanol. Give reason.arrow_forwardWhich of the following statements are true with respect to ether? Boiling point of ether is lower than that of alcohols. They are relatively inert. They react with metallic sodium. They react with oxidizing agents. They do not react with dilute bases.arrow_forward
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