Arrange the following compounds in order of: a) increasing boiling point, and b) increasing solubility in water. CH CHCCH CHỊCH,CHỊCH, "Q" CHỊCH, Học (8) butyl ethyl ether H₂C (A) 1. 2-pentanediol lowest bp Explain your answer. You don't need to rewrite the structures, just use the letter codes. a) Increasing boiling point: highest bp b) Increasing solubility in H₂O: least water-soluble CH-O-CH most water-soluble CH₂ CH3 (C) diisopropyl ether

Arrange the following compounds in order of: a) increasing boiling point, and b) increasing solubility in water. CH CHCCH CHỊCH,CHỊCH, "Q" CHỊCH, Học (8) butyl ethyl ether H₂C (A) 1. 2-pentanediol lowest bp Explain your answer. You don't need to rewrite the structures, just use the letter codes. a) Increasing boiling point: highest bp b) Increasing solubility in H₂O: least water-soluble CH-O-CH most water-soluble CH₂ CH3 (C) diisopropyl ether

Introduction to General, Organic and Biochemistry

11th Edition

ISBN:9781285869759

Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Chapter17: Aldehydes And Ketones

Section: Chapter Questions

Problem 17.54P: 17-54 Following is the structure of immunosuppressant FK-506, a molecule shown to disrupt...

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17-74 Glucose, C6H12O6, contains an aldehyde group but exists predominantly in the form of the cyclic hemiacetal shown here. We will discuss this cyclic form of glucose in Chapter 20. A cyclic hemiacetal is formed when the —OH group of one carbon bonds to the carbonyl group of another carbon. (a) Which carbon in glucose provides the —OH group and which provides the —CHO group? (b) Draw the alternative chair confirmations of D-glucose and state which of the two is the more stable.
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.
13-52 2,6-Di-/ezY-butyl-4-methylphenol (BHT, Section 13-4C) is an antioxidant added to processed foods to “retard spoilage.” How does BHT accomplish this goal?
17-3 1 Draw a structural formula for the principal organic product formed when each compound is treated with K2Cr2O7/H2SO4. If there is no reaction, say so. (a) Butanal (b) Benzaldehyde (c) Cyclohexanone (d) Cyclohexanol
16-19 2-Me thy 1 propane (bp -12°C), 2-propanol (bp 82°C), and 2-propanamine (bp 32°C) all have approximately the same molecular weight, yet their boiling points are quite different. Explain the reason for these differences.
13-20 Three products with the molecular formula CgH^BrCl form when bromobenzene is treated with chlorine, Cl2, in the presence of FeCl3 as a catalyst. Name and draw a structural formula for each product.
14-78 Consider alkenes A, B, and C. each of which has the same molecular formula, C(.H12. Alkenes B and C can each be separated into cis and trans isomers. Upon catalytic reduction using H,, in the presence of a transition metal catalyst (Ni, Pd, or Pt>, alkenes A, B, and C all give hexane as the only product. Acid- catalyzed hydration of alkene C gives one alcohol with the molecular formula CeH14O. Acid catalyzed- hydration of alkene B gives an equal mixture of two alcohols, each with the molecular formula C6H14O. Acid-catalyzed hydration of alkene C gives only a single alcohol with the molecular formula C6H14O. Propose structural formulas for alkenes A, B, and C and the alcohols formed by acid-catalyzed hydration of each, consistent with these experimental results.
13-43 (Chemical Connections 13E) Which features of Allura Red and Sunset Yellow make them water-soluble?
13-42 (Chemical Connections 13E) What are the differences in structure between Allura Red and Sunset Yellow?
13-21 The reaction of bromine with toluene in the presence of FeCl3 gives a mixture of three products, all with the molecular formula C7H7Br. Name and draw a structural formula for each product.
17-27 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.
17-54 Following is the structure of immunosuppressant FK-506, a molecule shown to disrupt calcineurin-mediated signal transduction in T-lymphocytes. (a) There are three carbon—carbon double bonds present in this molecule. Which of the three has the potential for cis/trans isomerism? Assign a cis or trans con?guration to each carbon-carbon double bond that has this possibility. (b) How many stereocenters are present in this molecule? How many stereoisomers are possible for it? (c) Are there any aromatic components in this molecule? (d) Consider the two carbon atoms marked with asterisks. Assign an R or S con?guration of each stereocenter. (e) Because of the presence of a 21-member ring, this molecule is described as a macrocycle. This ring is fashioned by three types of bonds, several carbon-carbon bonds, one ester, one hemiacetal, and one amide. Locate the ester and the hemiacetal. (f) Draw the structural formula of the long chain compound that would result if the hemiacetal were to be cleaved to an alcohol and a carbonyl group.