Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 12.5, Problem 9P
Interpretation Introduction
Interpretation: Among the given pair of
Concept introduction: The addition of
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How could 2,6-dimethylheptane be prepared from an alkyne and an alkyl halide? (The prime in R′ signifies that R and R′ can be different alkyl groups.)
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.
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?
Chapter 12 Solutions
Organic Chemistry (6th Edition)
Ch. 12.1 - Prob. 1PCh. 12.3 - Problem 12.2 What alkane is formed when each...Ch. 12.3 - Prob. 3PCh. 12.3 - Prob. 4PCh. 12.3 - Prob. 5PCh. 12.3 - Prob. 6PCh. 12.3 - Compound Molecular formula before...Ch. 12.4 - Problem 12.8 Draw the products formed when...Ch. 12.5 - Prob. 9PCh. 12.5 - Prob. 10P
Ch. 12.5 - Problem 12.11 (a) Draw the structure of a compound...Ch. 12.5 - Prob. 12PCh. 12.5 - Prob. 13PCh. 12.6 - Problem 12.14 Draw the products of each...Ch. 12.8 - Prob. 15PCh. 12.8 - Problem 12.16 Draw all stereoisomers formed when...Ch. 12.9 - Prob. 17PCh. 12.9 - Problem 12.18 Draw the products formed when both...Ch. 12.10 - Problem 12.19 Draw the products formed when each...Ch. 12.10 - Prob. 20PCh. 12.10 - Prob. 21PCh. 12.11 - Problem 12.22 Draw the products formed when each...Ch. 12.11 - Prob. 23PCh. 12.12 - Problem 12.24 Draw the organic products in each of...Ch. 12.13 - Prob. 25PCh. 12 - 12.29 Draw the products formed when A is treated...Ch. 12 - Prob. 30PCh. 12 - Prob. 31PCh. 12 - Prob. 32PCh. 12 - Prob. 33PCh. 12 - Draw the organic products formed when cyclopentene...Ch. 12 - Draw the organic products formed when allylic...Ch. 12 - Prob. 39PCh. 12 - Prob. 40PCh. 12 - Prob. 41PCh. 12 - What alkene is needed to synthesize each 1,2-diol...Ch. 12 - 12.48 Draw the products formed in each oxidative...Ch. 12 - What alkene or alkyne yields each set of products...Ch. 12 - Prob. 47PCh. 12 - Prob. 48PCh. 12 - Prob. 49PCh. 12 - Prob. 50PCh. 12 - 12.57 Draw the product of each asymmetric...Ch. 12 - 12.60 Identify A in the following reaction...Ch. 12 - Prob. 58PCh. 12 - 12.62 It is sometimes necessary to isomerize a cis...Ch. 12 - 12.63 Devise a synthesis of each compound from...Ch. 12 - Prob. 61P
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- 3 Give the systematic name of the given alkene based on its semi-structural formula. CH, CH, CH3 CH, - C = CH — с %3 CH - CH, CH - - CH2 CH, Systematic name:arrow_forwardDefine Propan-2-ol (CH3)2CHOH) ?arrow_forwardPyrethrins, such as jasmolin II (shown below), are a group of natural compounds that are synthesized by flowers of the genus Chrysanthemum (known as pyrethrum flowers) to act as insecticides. CH3 CH2=CH-CH. CH-C- -HCS 0-CH, CH,-C H2C- ČH, Which is not a functional group or structural feature in jasmolin II? cycloalkane carboxylic acid ester alkenearrow_forward
- Draw 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_forwardThe addition reaction of an acid (HBr) to an alkene (CH3CH=CH2) follows Markovnikov's rule and involves: A) initial attack by Br– B) initial attack by Br• C) isomerization of CH3CH2CH2Br D) formation of a primary carbocation. E) formation of a secondary carbonation. (F) Formation of allyl carbocationarrow_forwardThe heat of combustion of decahydronaphthalene (C10H18) is -6286 kJ/mol. The heat of combustion of naphthalene 1C10H82 is -5157 kJ/mol. (In both cases CO2(g) and H2O(l) are the products). Calculate the heat of hydrogenation and the resonance energy of naphthalene.arrow_forward
- What alkane, with molecular formula C5H12, forms only one monochlorinated product when it is heated with Cl2?arrow_forwardWhich products are formed when hydrobromic acid is added to (a) trans-2-hexene, (b) 2-methyl- 2-pentene, and (c) 4-methylcyclohexene, and how many regioisomers can be formed in each case?arrow_forward4d. polysubstituted benzene HO- O2N NO2 NH2 NO2arrow_forward
- Cyclopentene + H2arrow_forwardConsider the four trienes E–H. Rank compounds E–H in order of increasing heat of hydrogenation.arrow_forward46. In order to determine the ident ity of an alkene, a chemist reacts it with water. She then separates the product of this reaction into two equal amounts in conta iner X and container Y. To container X, a strong oxidizing agent is added. The resulting product will react with a base to form a salt and water. When the new product in container X is mixed with conta iner Y and H2SO4 is added, the chemist is able to confirm that: H3C CH2-C-0-CH2-CH2-CH3 has been formed. The identity of the alkene is which of the folow ing? a. с. H3C-CH-CH=CH-CH,-CH, b. H2CCH d. H;C-CH=CH, 47. What is the correct IUPÁC rame for compound below? H2-CH3 -C-CH2-CH2-CH-CH a. 2-ethy-5-hexanone b. 5-ethy-2-hexanone c. 3-methy-6-heptanone HC- d. 5-methy-2-heptanone e. 2-heptanone 48. Which one of the follow ing statements is incorrect? a primary amine contains the amino b. a secondary amine has a nitrogen which makes three single bonds a 3° amine will have a positive charge group, NH a. с. a secondary amine can…arrow_forward
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