ORGANIC CHEMISTRY - LOOSELEAF W/CONNECT
6th Edition
ISBN: 9781266060144
Author: SMITH
Publisher: MCG
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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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Which alkyne has the smaller heat of hydrogenation, HC≡CCH2CH2OH3 orCH3C≡CCH2CH3? Explain your choice.
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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.
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Chapter 12 Solutions
ORGANIC CHEMISTRY - LOOSELEAF W/CONNECT
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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- 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.arrow_forward3 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_forward
- Pyrethrins, 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_forwardDraw the condensed structure for the major product and indicate if no reactionarrow_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_forward
- Which one of the following compounds is an alkene? CH3-CH2-0-CH2–CH3 || CH 3-CH 2-C -H OH CH3 -CH-CH 3 CH3-CH-CH-CH2–CH3 O CH3-S-Harrow_forwardIUPAC structures for Alkynesarrow_forwardWhich reagent is needed to change an alkyne to an alkane? * Н:0+, Hg (COОH)2 N2, Pt Ог, Pd Н, Pt What reaction takes place when an alcohol is produced during the net addition of water across the double bond of an alkene? * Dehydrogenation Hydrogenation Dehydration Hydrationarrow_forward
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