Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 4.SE, Problem 62AP
Alcohols undergo an oxidation reaction to yield carbonyl compounds on treatment with CrO3. For example, 2-tert-butylcyclohexanol gives 2-tert-butylcyclohexanone. If axial –OH groups are generally more reactive than their equatorial isomers, which do you think reacts faster, the cis isomer of 2-tert-butylcyclohexanol or the trans isomer? Explain.
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1,4-Pentadiene (CH2=CH-CH2-CH=CH2) is a liquid at room temperature and has a density of 0.66 g/mL and molar mass of 68.12 g/mol. In a laboratory experiment, 3.80 mL of this compound was treated with 4.80 mL of conc. H2SO4 (100% w/w; molar mass 98.08 g/mol). Note that the density of conc. H2SO4 is 1.84 g/mL. The resulting sulfate ester was then treated with 1.20 mL of water (molar mass 18.02 g/mol) affording, after work- up, 2,4-pentanediol (molar mass 104.15 g/mol) as the crude product. The crude product was then purified by simple distillation, which yielded 2.00 g of pure product.
What is the theoretical yield of 2,4-pentanediol expressed in grams? Show calculations.
What is the percentage yield of pure 2,4-pentanediol?
1,4-Pentadiene (CH2=CH-CH2-CH=CH2) is a liquid at room temperature and has a density of 0.66 g/mL and molar mass of 68.12 g/mol. In a laboratory experiment, 3.80 mL of this compound was treated with 4.80 mL of conc. H2SO4 (100% w/w; molar mass 98.08 g/mol). Note that the density of conc. H2SO4 is 1.84 g/mL. The resulting sulfate ester was then treated with 1.20 mL of water (molar mass 18.02 g/mol) affording, after work- up, 2,4-pentanediol (molar mass 104.15 g/mol) as the crude product. The crude product was then purified by simple distillation, which yielded 2.00 g of pure product.
a.
Provide a balanced chemical equation to show the reaction between 1,4-pentadiene and sulfuric acid. Do not use molecular formulas in the chemical equation except for sulfuric acid.
b.
What reactant is the limiting reagent in this chemical equation? Show calculations to support your answer.
Chapter 4 Solutions
Organic Chemistry
Ch. 4.1 - Give IUPAC names for the following cycloalkanes:Ch. 4.1 - Draw structures corresponding to the following...Ch. 4.1 - Name the following cycloalkane:Ch. 4.2 - Prob. 4PCh. 4.2 - Draw the structures of the following molecules:...Ch. 4.2 - Prostaglandin F2α, a hormone that causes uterine...Ch. 4.2 - Name the following substances, including the cis-...Ch. 4.3 - Each H↔H eclipsing interaction in ethane costs...Ch. 4.3 - cis-1, 2-Dimethylcyclopropane has more strain than...Ch. 4.4 - Prob. 10P
Ch. 4.4 - Two conformations of cis-l, 3-dimethylcyclobutane...Ch. 4.6 - Draw two different chair conformations of...Ch. 4.6 - Draw two differant chair conformations of trans-1,...Ch. 4.6 - Prob. 14PCh. 4.7 - What is the energy difference between the axial...Ch. 4.7 - Prob. 16PCh. 4.7 - Look at Figure 4-12 on page 105, and estimate the...Ch. 4.8 - Draw the more stable chair conformation of the...Ch. 4.8 - Identify each substituent in the following...Ch. 4.9 - Which isomer is more stable, cis-decalin or...Ch. 4.9 - Look at the following structure of the female...Ch. 4.SE - Prob. 22VCCh. 4.SE - Name the following compound, identify each...Ch. 4.SE - A trisubstituted cyclohexane with three...Ch. 4.SE - The following cyclohexane derivative has three...Ch. 4.SE - Prob. 26VCCh. 4.SE - Draw the five cycloalkanes with the formula C5H10.Ch. 4.SE - Draw two constitutional isomers of cis-1,...Ch. 4.SE - Prob. 29APCh. 4.SE - Tell whether the following pairs of compounds are...Ch. 4.SE - Prob. 31APCh. 4.SE - Prob. 32APCh. 4.SE - Draw 1, 3, 5-trimethylcyclohexane using a hexagon...Ch. 4.SE - Hydrocortisone, a naturally occurring hormone...Ch. 4.SE - A 1, 2-cis disubstituted cyclohexane, such as...Ch. 4.SE - A 1, 2-trans disubstituted cyclohexane must have...Ch. 4.SE - Prob. 37APCh. 4.SE - Which is more stable, a 1, 4-trans disubstituted...Ch. 4.SE - cis-1, 2-Dimethylcyclobutane is less stable than...Ch. 4.SE - From the data in Figure 4-12 and Table 4-1,...Ch. 4.SE - Prob. 41APCh. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Galactose, a sugar related to glucose, contains a...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - The diaxial conformation of cis-1,...Ch. 4.SE - Approximately how much steric strain does the...Ch. 4.SE - In light of your answer to Problem 4-43, draw the...Ch. 4.SE - Prob. 50APCh. 4.SE - Prob. 51APCh. 4.SE - Using molecular models as well as structural...Ch. 4.SE - trans-Decalin is more stable than its cis isomer,...Ch. 4.SE - As mentioned in Problem 3-53, the statin drugs,...Ch. 4.SE - myo-Inositol, one of the isomers of...Ch. 4.SE - How many cis–trans stereoisomers of myo-inositol...Ch. 4.SE - The German chemist J. Bredt proposed in 1935 that...Ch. 4.SE - Tell whether each of the following substituents on...Ch. 4.SE - Prob. 59APCh. 4.SE - Prob. 60APCh. 4.SE - Ketones react with alcohols to yield products...Ch. 4.SE - Alcohols undergo an oxidation reaction to yield...
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- Ethylene oxide reacts readily with HO- because of the strain in the three-membered ring. Explain why cyclopropane, a compound with approximately the same amount of strain, does not react with HO-.arrow_forwardAs we learned in Chapter 4, monosubstituted cyclohexanes exist as an equilibrium mixture of two conformations having either an axial or equatorial substituent. When R = CH2CH3, Keq for this process is 23.When R = C(CH3)3, Keq for this process is 4000. a.When R = CH2CH3, which conformation is present in higher concentration? b.Which R shows the higher percentage of equatorial conformation at equilibrium? c. Which R shows the higher percentage of axial conformation at equilibrium? d. For which R is ΔGo more negative? e.How is the size of R related to the amount of axial and equatorial conformations at equilibrium?arrow_forwardAnswer the following questions about compound A, which contains a CH3 group and OH group bonded to the carbon skeleton that consists of three six-membered rings in the conformation shown a.) Are the CH3 and OH groups oriented cis or trans to each other?b.) Is a substituent on Ca that is cis to the CH3 group located in the axial or equatorial position? c.) Is an equatorial Br at Cb oriented cis or trans to the OH group?d.) Is the H atom on Cc located cis or trans to the OH group?e.) Is a substituent on Cd that is trans to the OH group located in the axial or equatorial position?arrow_forward
- Answer the following questions about compound A, which contains a CH3 group and OH group bonded to the carbon skeleton that consists of three six-membered rings in the conformation shown.a.Are the CH3 and OH groups oriented cis or trans to each other? b. Is a substituent on Ca that is cis to the CH3 group located in the axial or equatorial position? c. Is an equatorial Br at Cb oriented cis or trans to the OH group? d. Is the H atom on Cc located cis or trans to the OH group? e.Is a substituent on Cd that is trans to the OH group located in the axial or equatorial position?arrow_forwardDraw the following organic compounds: a) 2-Methylhexa-1,5-diene b) 3-Ethyl-2,2-dimethylhept-3-ene c) (4E)-2,4-Dimethylhexa-1,4-diene d) cis-3,3-Dimethyl-4propylocta-1,5-diene e) trans-1-Bromo-3-chloracyclopentane f) isopropyl bromide g) 3,3-Dimethyloct-4-yne h) 3-Ethyl-5-methyl-1,6,8-decatriyne i) 2,2,5,5-Tetramethylhex-3-yne j) 3,4-Dimethylcyclodecynearrow_forwardA2 1. An alkyne with molecular formula C5H10 2. A ketone with molecular formula C4H8O 3. A ketone with molecular formula C3H8O 4. An alkene with molecular formula C5H8 5. An alkene with molecular formula C5H10 6. An aldehyde with molecular formula C2H4O 7. An aldehyde with molecular formula CH4O 8. A saturated hydrocarbon with molecular formula C6H14arrow_forward
- Draw the structure of each molecule below and put an asterisk on each tetrahedral stereocenter. i) 3,4-dichlorohexane ii) 3-bromo-1-iodo-5-methylhexane iii) 3-bromo-2,4-dimethylpentanearrow_forwardUnder certain reaction conditions, 2,3-dibromobutane reacts with two equivalents of base to give three products, each of which contains two new p bonds. Product A has two sp hybridized carbon atoms, product B has one sp hybridized carbon atom, and product C has none. What are the structures of A, B, and C?arrow_forwardDraw the skeletal (bond-line) structures of all isomers of C4H8O (including configurational isomers) that contain an alkene and an ether. There should be 5 structures.arrow_forward
- Write the bond line formula of the following compounds: (a) 4-methyl-2-hexene, two geometrical (stereoisomers) isomers (b) 3-fluoro-2-methylheptanol (3-fluoro-2-methylheptan-1-ol) (c) 4-methyl-hex-1-yn-3-olarrow_forward(1R)-1-chloro-1-cyclohexylpropan-1-ol Draw the bond-line structure of the said compoundarrow_forwardWhen cyclopropane is treated with HI, 1-idopropane is formed. A similar type of reaction does not occur with cyclopentene or Cyclohexane. Suggest an explanation for cyclopropane’s reactivity.arrow_forward
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