EP ESSENTIAL ORG.CHEM.-MOD.MASTERING
3rd Edition
ISBN: 9780133858501
Author: Bruice
Publisher: PEARSON CO
expand_more
expand_more
format_list_bulleted
Textbook Question
Chapter 13, Problem 27P
Explain why the pKa of a hydrogen bonded to the sp3 carbon of propene is greater (pKa = 42) than that of any of the carbon acids listed in Table 13.1, but is less than the pKa of an
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
What accounts for the geometry (pyramidalization) of the NH2 group in aniline?
1. Resonance between the NH2 group and the benzene ring.
2. The electronic withdrawing nature of the sp2 carbons in the phenyl group.
3. Participation of the nitrogen lone pair to make the system aromatic.
4. Both 1 and 3.
True or False
1. With alkynes having 2 pi bonds, they have more electron-rich region than alkenes and, thus, are more reactive than alkenes.
2. Hydrobromination of an alkene follows anti-Markovnikov’s rule in the presence of a peroxide.
3. The reaction of BH3 with 2-methylbut-2-ene results in the attachment of a hydroxyl group, OH, on the third carbon since this carbon is less substituted.
4. The reduction of an alkyne using a strong base such as LiNH2 gives an alkane when 2 equivalents of hydrogen gas is added.
what is the role of conc. H2SO4 in molisch's reagent test?
Chapter 13 Solutions
EP ESSENTIAL ORG.CHEM.-MOD.MASTERING
Ch. 13.1 - Identify the most acidic hydrogen in each...Ch. 13.1 - Prob. 2PCh. 13.1 - Prob. 3PCh. 13.1 - Prob. 4PCh. 13.1 - Explain why HO cannot remove a proton from the...Ch. 13.2 - Prob. 6PCh. 13.2 - Prob. 7PCh. 13.3 - Prob. 8PCh. 13.3 - Prob. 9PCh. 13.3 - Prob. 10P
Ch. 13.4 - Prob. 11PCh. 13.5 - Prob. 12PCh. 13.5 - Prob. 13PCh. 13.6 - Prob. 14PCh. 13.7 - Prob. 16PCh. 13.8 - Prob. 17PCh. 13.8 - Prob. 18PCh. 13.8 - Prob. 19PCh. 13.9 - Prob. 20PCh. 13.10 - Propose a mechanism for the formation of...Ch. 13.10 - Prob. 22PCh. 13.10 - a. If the biosynthesis of palmitic acid were...Ch. 13 - Draw the enol tautomers for each of the following...Ch. 13 - Number the following compounds in order from...Ch. 13 - Prob. 26PCh. 13 - Explain why the pKa of a hydrogen bonded to the...Ch. 13 - Prob. 28PCh. 13 - Prob. 29PCh. 13 - Prob. 30PCh. 13 - Prob. 31PCh. 13 - Prob. 32PCh. 13 - Prob. 33PCh. 13 - Using cyclopentanone as the reactant, show the...Ch. 13 - Prob. 35PCh. 13 - Prob. 36PCh. 13 - Prob. 37PCh. 13 - Prob. 38PCh. 13 - Prob. 39PCh. 13 - Prob. 40PCh. 13 - Prob. 41PCh. 13 - Prob. 42PCh. 13 - Prob. 43PCh. 13 - Prob. 44PCh. 13 - Describe how the following compounds can be...Ch. 13 - Prob. 46PCh. 13 - Which would require a higher temperature:...Ch. 13 - Prob. 48PCh. 13 - Propose a mechanism for the following reaction:Ch. 13 - Show how the following compounds could be...Ch. 13 - Prob. 51PCh. 13 - Prob. 52P
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- HOCH2CH2OH O: H* Br2 (excess) 7. NaOCH3 C6H5 CH3OH 5. 6.arrow_forwardWhat changes would be made to separate the two isomeric pinene (α and β), bp 156 oC and 167 oC respectively that are the major constituents of commercial turpentine?arrow_forwardGive a brief answer to explain why acetic acid has a much higher BP (118 C) than 1- propanol (BP = 97 C) even though they both have the same size (molecular weight = 60) and they both form Hydrogen bonds.arrow_forward
- Give the organic reaction products for the following reaction a. b. a. b. CH3CH2-C. ง ว NaOH ? + ? N(CH3)2 H₂O H*/H₂O CH3-C-OCH2CH3 ? + ?arrow_forwardDraw the skeletal structure of the indicated product. MgBr + (2 equivalents) 1. diethyl ether 2. D30* aromatic ring-containing major organic product A other + organic product Barrow_forwardWhich is/are correct? a.The dipole moment of propanal is greater than that of 1-butene. b.Carbonyl compounds are more soluble in water than the corresponding alkanes but less than the corresponding alcohols. c.All the choices. d.The boiling points of 2-propanol, propanone, and 2-methylpropene are 82C, 57C, and -7C, respectively.arrow_forward
- Specialized reagents and their acronyms: MCPBA= meta-chloroperbenzoic acid; HOAC = acetic acid, NaOAc = Sodium Acetate; Ph= phenyl = C6H5-; P(Ph)3 = triphenyl phosphine; NBS = N- bromosuccinimide, PBr3, SOCI2, AICI3, FeBr3, H2SO4, Li, Na, Mg, Br2, CrO3, LDA = lithium diisopropylamide, PCC = pyridinium chlorochromate, KO-C(CH3)3, LAH = LIAIH4, (sia)2BH = disecondary isobutyl borane, KMNO4, HIO4 = periodic acid %3D %3D %3D %3D %3D write the missing reagents and solvents over the arrows. Some transformation require multiple steps. In some cases there will be multiple arrows. Ph CH CH o 0om ilubongo CEC-Ph In questions 14-24, write the products of the following transformations. If there is no reaction write NR. Indicate R or S or racemic or indicate cis or trans where appropriate OH + LDA THF solvent (S) Pharrow_forward13arrow_forwardHh.148.arrow_forward
- Modified True or False. Write correct if the statement is True and if false write the word/s that make it false and beside it write the word/s that will make the statement true. 4. Lone pair delocalization decreases the positivity of carbonyl carbon.5. The longer the carbon chain, the higher the boiling point.6. sp3 is 75% p character and this allows C-H hyper conjugation.7. The higher the electronegativity, the higher the temperature needed to break bonds.8. Steric effect increases the boiling point.9. Stearic effect increases the Van der Waals forces.10. Lone pair delocalization decreases the positivity of carbonyl carbon.11. Amines are considered basic.12. The stronger the Van der Waals forces between molecules of the same substance, themore soluble the substance is in water.13. The longer the carbon chain, the lower the solubility of the substance in water.14. Alkanes with less than 6 carbon atoms are gases.15. Stearic effects enhances the solubility in water.16. H-bond can exist…arrow_forward20. In the IUPAC name for the following compound, the -Br group is located on carbon number_? CH;CHCH=CH, Br a. 1 b. 2 С. 3 d. 4arrow_forward2. An attempted dehydration of propan-1-ol (CH3CH₂CH₂OH) with H₂SO4 at 135°C gave a product (b.p. 89°C, C6H140) that when tested gave the following results: Baeyer Test: Br₂/CC14 Test: Chromic Acid Test: Negative Negative Negative Propose a structure for the odd product and explain its formation.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningIntroductory Chemistry: An Active Learning Approa...ChemistryISBN:9781305079250Author:Mark S. Cracolice, Ed PetersPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Introductory Chemistry: An Active Learning Approa...
Chemistry
ISBN:9781305079250
Author:Mark S. Cracolice, Ed Peters
Publisher:Cengage Learning
Seven Name Reactions in One - Palladium Catalysed Reaction (047 - 053); Author: Rasayan Academy - Jagriti Sharma;https://www.youtube.com/watch?v=5HEKTpDFkqI;License: Standard YouTube License, CC-BY