Organic Chemistry - With Access (Custom)
4th Edition
ISBN: 9781259147760
Author: OHIO UNIV.
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 9, Problem 9.43P
Rank each group of compounds in order of:
a. increasing boiling point: CH3CH2CH2OH, (CH3)2CHOH, CH3CH2OCH3
b. increasing water solubility: CH3(CH2)5OH, OH(CH2)6OH, CH3(CH2)4CH3
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Which member of each pair is more soluble in water? Why?(a) CH₃CH₂OCH₂CH₃(l) or CH₃CH₂OCH₃(g)(b) CH₂Cl₂(l) or CCl₄(l)
n-Butyl methyl ether is an isomer of MTBE and has a boiling point of 70 oC. Explain why the boiling point is significantly different compared to MTBE.
Dimethyl ether (CH3OCH3) and ethanol (CH3CH2OH) are isomers, butCH3OCH3 has a pKa of 40 and CH3CH2OH has a pKa of 16. Why are thesepKa values so different?
Chapter 9 Solutions
Organic Chemistry - With Access (Custom)
Ch. 9 - Draw all constitutional isomers having molecular...Ch. 9 - Prob. 9.2PCh. 9 - Give the IUPAC name for each compound.Ch. 9 - Problem 9.3 Give the structure corresponding to...Ch. 9 - Prob. 9.5PCh. 9 - Name CH33COCH3, a gasoline additive commonly...Ch. 9 - Name each epoxide.
a. (two ways) b. c. (two...Ch. 9 - Problem 9.6 Rank the following compounds in order...Ch. 9 - Which mechanism is favored by the use of crown...Ch. 9 - Draw the organic product of each reaction.
Ch. 9 - Prob. 9.11PCh. 9 - Prob. 9.12PCh. 9 - Prob. 9.13PCh. 9 - Prob. 9.14PCh. 9 - Problem 9.13 Draw the structure of each...Ch. 9 - What other alkene is also formed along with Y in...Ch. 9 - Prob. 9.17PCh. 9 - Explain how the reaction of CH32CHCHCl CH3 with...Ch. 9 - Prob. 9.19PCh. 9 - Draw the products of each reaction, indicating the...Ch. 9 - Problem 9.19 What is the major product formed...Ch. 9 - Prob. 9.22PCh. 9 - Prob. 9.23PCh. 9 - Problem 9.22 Draw the organic products formed in...Ch. 9 - Problem 9.23 Draw two steps to convert into each...Ch. 9 - Draw the products of each reaction, and indicate...Ch. 9 - Draw the products of each reaction, and include...Ch. 9 - Draw the products formed when (S)-butan-2-ol is...Ch. 9 - Prob. 9.29PCh. 9 - Prob. 9.30PCh. 9 - Explain why the treatment of anisole with HBr...Ch. 9 - Prob. 9.32PCh. 9 - The cis and trans isomers of 2, 3-dimethyloxirane...Ch. 9 - Problem 9.36 Draw the product of each...Ch. 9 - 9.37 Name each compound depicted in the...Ch. 9 - Answer each question using the ball-and-stick...Ch. 9 - Prob. 9.37PCh. 9 - a. Draw the structure of 1, 2, and 3 alcohol with...Ch. 9 - Give IUPAC name for each alcohol. a....Ch. 9 - Name each ether and epoxide. a.b.c.d.Ch. 9 - Prob. 9.41PCh. 9 - Draw the eight constitutional isomers with...Ch. 9 - Rank each group of compounds in order of: a....Ch. 9 - Prob. 9.44PCh. 9 - 9.44 Why is the boiling point of higher than...Ch. 9 - Draw the organic products formed when CH3CH2CH2OH...Ch. 9 - Draw the organic products formed when 1-methyl...Ch. 9 - What alkenes are formed when each alcohol is...Ch. 9 - Prob. 9.49PCh. 9 - Prob. 9.50PCh. 9 - 9.48 Draw the products of each reaction and...Ch. 9 - Prob. 9.52PCh. 9 - 9.52 Draw a stepwise mechanism for the following...Ch. 9 - 9.53 Although alcohol V gives a single alkene W...Ch. 9 - Prob. 9.55PCh. 9 - Prob. 9.56PCh. 9 - Prob. 9.57PCh. 9 - When CH3CH2CH2CH2OH is treated with H2SO4 NaBr,...Ch. 9 - 9.57 Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 9.60PCh. 9 - Draw two different routes to each of the following...Ch. 9 - Prob. 9.62PCh. 9 - Prob. 9.63PCh. 9 - 9.62 Draw a stepwise mechanism for each...Ch. 9 - Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 9.66PCh. 9 - Draw the products of each reaction. a.c. b.d.Ch. 9 - When each halohydrin is treated with, a product of...Ch. 9 - Prob. 9.69PCh. 9 - Devise a stepwise mechanism for the following...Ch. 9 - Draw the products of each reaction, and indicate...Ch. 9 - Prepare each compound from CH3CH2CH2CH2OH. More...Ch. 9 - Prepare each compound from cyclopentanol. More...Ch. 9 - 9.72 Identify the reagents (a–h) needed to carry...Ch. 9 - Prob. 9.75PCh. 9 - 9.74 Treatment of with affords compound A and ....Ch. 9 - Prob. 9.77PCh. 9 - Prob. 9.78PCh. 9 - 9.77 Draw a stepwise, detailed mechanism for the...Ch. 9 - Dehydration of 1, 2, 2-trimethylcyclohexanol with...Ch. 9 - Prob. 9.81PCh. 9 - 9.80 Draw a stepwise mechanism for the following...Ch. 9 -
9.81 Aziridines are heterocycles that contain an...
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
- arrange the compounds in each set in order of decreasing solubility in water. Q. 1-Hexanol, 1,2-hexanediol, hexanearrow_forwarda. What is the chemical structure of biphenyl? b. Is it polar or nonpolar? _______________________ c. What is its water solubility in g/L? __________________________arrow_forwardExplain why CH3CH2NHCH3 has a higher boiling point than (CH3)3N, even though they have the same molecular weight.arrow_forward
- Rank the following groups in order of decreasing priority. −C≡CH, −CH(CH3)2, −CH2CH3, −CH=CH2arrow_forward) Which of the following compounds will be most soluble in ethanol (CH3CH2OH)? A) ethylene glycol (HOCH2CH2OH) B) hexane (CH3CH2CH2CH2CH2CH3) C) acetone (CH3COCH3)D) trimethylamine (N(CH3)3) E) A and D are soluble in ethanol.arrow_forwardRank the following compounds in order of increasing water solubility: glucose, hexane [CH 3(CH 2) 4CH 3], and 1-decanol [CH 3(CH 2) 9OH]. Explain your choice.arrow_forward
- (a) Give the IUPAC name for A and B. (b) Draw the product formed when A or B is treated with each reagent: [1] NaBH4, CH3OH; [2] CH3MgBr, then H2O; [3] Ph3P = CHOCH3; [4] CH3CH2CH2NH2, mild acid; [5] HOCH2CH2CH2OH, H+.arrow_forwardWhich member of each pair has the lower boiling point? Explain your choice. ***When you draw the diagrams, how do you draw the dipoles when you have CH3 CH2CH2CH3? Like how do you determine the CH3 or CH2 have the dipole. Thank you.arrow_forwardALCOHOLS 1. WHY IS ETHANOL MORE SOLUBLE IN WATER THAN 1-HEXANOL? 2. WHAT IS DENATURED ALCOHOL? AND WHY IS ALCOHOL DENATURED? ETHER 1. WHY DOES DIETHYL ETHER HAVE MUCH LOWER BOILING POINT THAN 1-BUTANOL?arrow_forward
- "A research team synthesizes a novel organic compound 'X' with the molecular formula C5H8O2. When 'X' is treated with a deuterated acid (D2O), a single deuterium atom replaces a hydrogen atom, forming compound 'Y' (C5H7DO2). 'X' does not react with 2,4-Dinitrophenylhydrazine (2,4-DNP) but does react with both Tollens' reagent and Benedict's solution, forming a silver mirror and a red precipitate, respectively. Furthermore, 'X' undergoes catalytic hydrogenation over a palladium catalyst, consuming one mole of hydrogen to form a compound 'Z' (C5H10O2). Based on these observations, what is the most likely structure of compound 'X'?" A. Methyl vinyl ketone B. 3-Buten-2-one C. Acetoacetic ester D. 2-Hydroxypent-3-enalarrow_forwardExplain the process of Conversion of hexan-2-ol to other compounds ?arrow_forwardDraw the product formed when C6H5N2 +Cl− reacts with each compound.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 Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Nomenclature: Crash Course Chemistry #44; Author: CrashCourse;https://www.youtube.com/watch?v=U7wavimfNFE;License: Standard YouTube License, CC-BY