Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 5.7, Problem 17P
Which of the following have a meso form? (Recall that the -ol suffix refers to an alcohol, ROH.)
(a) 2, 3-Butanediol
(b) 2, 3-Pentanediol
(c) 2, 4-Pentanediol
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In each pair of compounds, select the one with the higher boiling point.
(a) Acetaldehyde or ethanol
(b) Acetone or 3-pentanone
(c) Butanal or butane
(d) Butanone or 2-butanol
(a)({)-hexane-3,4-diol, label each structure you have drawn as chiral or achiral.
Predict which member of each group is most soluble in water, and explain the reasons for your predictions.(a) butan-1-ol, pentan-1-ol, or propan-2-ol(b) chlorocyclohexane, cyclohexanol, or cyclohexane-1,2-diol(c) phenol, cyclohexanol, or 4-methylcyclohexanol
Chapter 5 Solutions
Organic Chemistry
Ch. 5.2 - Prob. 1PCh. 5.2 - Prob. 2PCh. 5.2 - Prob. 3PCh. 5.2 - Prob. 4PCh. 5.3 - Is cocaine (Worked Example 5-2) dextrorotatory or...Ch. 5.3 - Prob. 6PCh. 5.5 - Prob. 7PCh. 5.5 - Prob. 8PCh. 5.5 - Prob. 9PCh. 5.5 - Assign R or S configuration to the chirality...
Ch. 5.5 - Draw a tetrahedral representation of...Ch. 5.5 - Prob. 12PCh. 5.6 - One of the following molecules (a)–(d) is...Ch. 5.6 - Prob. 14PCh. 5.6 - Assign R or S configuration to each chirality...Ch. 5.7 - Prob. 16PCh. 5.7 - Which of the following have a meso form? (Recall...Ch. 5.7 - Does the following structure represent a meso...Ch. 5.8 - Prob. 19PCh. 5.8 - Prob. 20PCh. 5.9 - Prob. 21PCh. 5.11 - Prob. 22PCh. 5.11 - Prob. 23PCh. 5.11 - The lactic acid that builds up in tired muscles is...Ch. 5.11 - The aconitase-catalyzed addition of water to...Ch. 5.SE - Which of the following structures are identical?...Ch. 5.SE - Prob. 27VCCh. 5.SE - Prob. 28VCCh. 5.SE - Assign R or S configuration to each chirality...Ch. 5.SE - Prob. 30VCCh. 5.SE - Prob. 31APCh. 5.SE - Which of the following compounds are chiral? Draw...Ch. 5.SE - Prob. 33APCh. 5.SE - Eight alcohols have the formula C5H12O. Draw them....Ch. 5.SE - Draw compounds that fit the following...Ch. 5.SE - Prob. 36APCh. 5.SE - Prob. 37APCh. 5.SE - Prob. 38APCh. 5.SE - What is the stereochemical configuration of the...Ch. 5.SE - Prob. 40APCh. 5.SE - Prob. 41APCh. 5.SE - Prob. 42APCh. 5.SE - Prob. 43APCh. 5.SE - Assign R or S configuration to each chirality...Ch. 5.SE - Assign R or S configuration to each chirality...Ch. 5.SE - Prob. 46APCh. 5.SE - Assign R or S configuration to each chirality...Ch. 5.SE - Assign R or S configurations to the chirality...Ch. 5.SE - Assign R or S stereochemistry to the chirality...Ch. 5.SE - Prob. 50APCh. 5.SE - Draw examples of the following: (a) A meso...Ch. 5.SE - Prob. 52APCh. 5.SE - Prob. 53APCh. 5.SE - Prob. 54APCh. 5.SE - On reaction with hydrogen gas by a platinum...Ch. 5.SE - Prob. 56APCh. 5.SE - Prob. 57APCh. 5.SE - One of the steps in fat metabolism is the...Ch. 5.SE - The dehydration of citrate to yield cis-aconitate,...Ch. 5.SE - The first step in the metabolism of glycerol,...Ch. 5.SE - One of the steps in fatty-acid biosynthesis is the...Ch. 5.SE - Prob. 62APCh. 5.SE - Draw tetrahedral representations of the two...Ch. 5.SE - The naturally occurring form of the amino acid...Ch. 5.SE - Prob. 65APCh. 5.SE - Prob. 66APCh. 5.SE - Prob. 67APCh. 5.SE - Allenes are compounds with adjacent carbon-carbon...Ch. 5.SE - Prob. 69APCh. 5.SE - Prob. 70APCh. 5.SE - How many stereoisomers of...Ch. 5.SE - Draw both cis- and trans-1,4-dimethylcyclohexane...Ch. 5.SE - Draw both cis- and trans-1,3-dimethylcyclohexane...Ch. 5.SE - cis-1,2-Dimethylcyclohexane is optically inactive...Ch. 5.SE - Prob. 75APCh. 5.SE - Prob. 76APCh. 5.SE - Prob. 77AP
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- For each pair of compounds, predict which compound has a higher boiling point. then explain why that compound has a higher boiling point. (a) isopropyl bromide and n-butyl bromide (b) isopropyl chloride and tert-butyl bromide (c) 1-bromobutane and 1-chlorobutanearrow_forwardDescribe how would you distinguish the following pairs, (a) Benzene and cyclohexane (b) Phenol and toluene (c) Phenol and benzoic acid (d) methanol and isopropyl alcoholarrow_forwardThe cis ketone A is isomerized to a trans ketone B with aqueous NaOH. A similar isomerization does not occur with ketone C. (a) Draw the structure of B using a chair cyclohexane. (b) Label the substituents in C as cis or trans, and explain the difference in reactivity.arrow_forward
- 4 But-2-enal, CH₂CH=CHCHO, is a pale yellow, flammable liquid with an irritating odour. (a) But-2-enal exists as two stereoisomers. Draw skeletal formulae to show the structure of the two stereoisomers of but-2-enal. (b) (i) Describe a simple chemical test that would show that but-2-enal is an aldehyde. (ii) Explain why this test gives a different result with aldehydes than it does with keton (c) But-2-enal also reacts with sodium borohydride, NaBH4. (i) Identify the organic compound formed in this reaction. (ii) State the type of chemical reaction occurring. (d) Precautions must be taken to prevent but-2-enal catching fire. Construct a balanced equation for the complete combustion of but-2-enal, C₂HO.arrow_forward17) Which of the following compounds does not have the molecular formula C6H140? (a) 1-hexanol (b) 2-hexanol (c) 3-methyl-2-pentanol (d) 3-methyl-3-pentanol (e) Cyclohexanolarrow_forwardA The alkyl group (CH3)2CH- is a(n) group. (a) tert-butyl (b) iso-butyl (c) n-butyl (d) sec-butyl (e) iso-propyl B In the box to the right of each molecule, draw a constitutional (structural) isomer of it. Br: NH₂arrow_forward
- 6. Describe concisely a chemical test to distinguish between the following pairs of compounds. (a) n-pentanol and 3-methylpentan-3-ol (b) Ethanal dan pentanal (c) Phenol and benzoic acidarrow_forwardDescribe how would you distinguish the following pairs, (a) Benzene and cyclohexane (b) Phenol and toluene (c) Phenol and benzoic acidarrow_forward(a) Draw the structure of the following :(i) p-Methylbenzaldehyde (ii) 4-Methylpent-3-en-2-one(b) Give chemical tests to distinguish between the following pairs of compounds :(i) Benzoic acid and Ethyl benzoate, (ii) Benzaldehyde and Acetophenone.(iii) Phenol and Benzoic acid.arrow_forward
- 4. Which of the following has a higher boiling point? Explain your answer:(a) 2-propanol or 2-butanol(b) Dimethyl ether or ethanolarrow_forwardDraw structural formulas for these ketones. (a) Ethyl isopropyl ketone (b) 2-Chlorocyclohexanone (c) 2,4-Dimethyl-3-pentanone (d) Diisopropyl ketone (e) Acetone (f) 2,5-Dimethylcyclohexanonearrow_forwardShow the chemical reaction on how to convert cyclopentene into these compounds. (a) 1,2-dimethylcyclopropane (b) Cyclopentanol (c) Iodocyclopentane (d) Cyclopentane.arrow_forward
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