Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 14, Problem 14.45SP
Show how you would synthesize the following ethers in good yield from the indicated starting materials and any additional reagents needed.
- a. cyclopentyl n-propyl ether from cyclopentanol and propan-1-ol
- b. n-butyl phenyl ether from phenol and butan-1-ol
- c. 2-ethoxyoctane from an octane
- d. 1-methoxydecane from a decene
- e. 1-ethoxy-1-methylcyclohexane from 2-methylcyclohexanol
- f. trans-2,3-epoxyoctane from octan-2-ol
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
The product of the electrophilic addition of 3-methyl-2-hexene with propanol and
bromine will produce the following major product with the following in it's name:
O a. 2-ethyl ether and 3 bromine
O b. 2-ethyl ether and 4 bromine
O c. 2-ethyl ether and 2 bromine
O d. 3-ethyl ether and pentane
O e. 3-ethyl ether and 2 bromine
Which of the following alkenes will yield 3-bromo-3-methylpentane as the major
product upon addition of HBr?
IV
Ol only
Oll and II only
OiV only
Oll only
OAII of them
The product of the electrophilic addition of 3-methyl-2-hexene with propanol and bromine will produce the following major product with the following in it's
name:
O a. 3-ethyl ether and 2 bromine
O b. 2-ethyl ether and 3 bromine
O c. 2-ethyl ether and 2 bromine
O d. 3-ethyl ether and pentane
O e. 2-ethyl ether and 4 bromine
11. Predict the product when cis-3-methylcyclopentanol is treated with TsCl/pyridine, followed by sodium
bromide.
a.
trans-1-bromo-3-methylcyclopentane
b. cis-1-bromo-3-methylcyclopentane
c. 1-methylcyclopentene
d. 2-methylcyclopentene
e. 3-methylcyclopentene
Chapter 14 Solutions
Organic Chemistry (9th Edition)
Ch. 14.2C - Rank the given solvents in decreasing order of...Ch. 14.2D - Prob. 14.2PCh. 14.2D - In the presence of 18-crown-6, potassium...Ch. 14.3B - Give a common name (when possible) and a...Ch. 14.3C - Prob. 14.5PCh. 14.3C - Name the following heterocyclic ethers.Ch. 14.4 - Propose a fragmentation to account for each...Ch. 14.5 - Prob. 14.8PCh. 14.5 - Prob. 14.9PCh. 14.6 - Prob. 14.10P
Ch. 14.7 - Explain why bimolecular condensation is a poor...Ch. 14.7 - Prob. 14.12PCh. 14.7 - Prob. 14.13PCh. 14.8 - Prob. 14.14PCh. 14.8 - Prob. 14.15PCh. 14.8 - Prob. 14.16PCh. 14.10A - Prob. 14.17PCh. 14.10A - Prob. 14.18PCh. 14.10B - Prob. 14.19PCh. 14.11B - Show how you would accomplish the following...Ch. 14.11B - Prob. 14.21PCh. 14.12 - Prob. 14.22PCh. 14.12 - Prob. 14.23PCh. 14.12 - Prob. 14.24PCh. 14.13 - Prob. 14.25PCh. 14.13 - Prob. 14.26PCh. 14.14 - Prob. 14.27PCh. 14.15 - Give the expected products of the following...Ch. 14 - Write structural formulas for the following...Ch. 14 - Give common names for the following compounds. a....Ch. 14 - Give IUPAC names for the following compounds. a....Ch. 14 - Glycerol (propane-1,2,3-triol) is a viscous syrup...Ch. 14 - Prob. 14.33SPCh. 14 - Show how you would make the following ethers,...Ch. 14 - (A true story.) An inexperienced graduate student...Ch. 14 - Prob. 14.36SPCh. 14 - a. Show how you would synthesize the pure (R)...Ch. 14 - a. Predict the values of m/z and the structures of...Ch. 14 - The following reaction resembles the...Ch. 14 - Prob. 14.40SPCh. 14 - Prob. 14.41SPCh. 14 - Prob. 14.42SPCh. 14 - Give the structures of the intermediates...Ch. 14 - Prob. 14.44SPCh. 14 - Show how you would synthesize the following ethers...Ch. 14 - Prob. 14.46SPCh. 14 - Prob. 14.47SPCh. 14 - Prob. 14.48SPCh. 14 - An acid-catalyzed reaction was carried out using...Ch. 14 - Propylene oxide is a chiral molecule. Hydrolysis...Ch. 14 - Prob. 14.51SPCh. 14 - Prob. 14.52SPCh. 14 - Prob. 14.53SPCh. 14 - Prob. 14.54SPCh. 14 - In 2012, a group led by Professor Masayuki Satake...
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
- Specify both the alcohol starting material and the reagents you would use in each step in a synthesis of the compound shown. If the synthesis requires only two steps enter "none" for step 3. r Alcohol Starting Materials 1. methanol 2. ethanol 3. 1-propanol 4. 2-propanol 5. cyclohexanol Reagents available a. LiAlH₁ f. PBr3 b. H₂SO4 c. HCI d. HBr i. CH3 MgBr; then H3O+ e. SOC1₂ j. CH3 CH₂ MgBr; then H3O+ g. CrO3, H₂ SO4, H₂O h. NaH k. CH3 CH₂ CH₂ MgBr; then H3O+ I. C6H5 MgBr (phenylmagnesium bromide); then H3O+ m. (CH3)2 CHMgBr: then H3O+t n. Dess-Martin periodinane (DMP) Write the number/letters of the alchol/reagents in the boxes below. Alcohol starting material Reagent for step 1 Reagent for step 2 Reagent for step 3arrow_forwardSpecify both the alcohol starting material and the reagents you would use in each step in a synthesis of the compound shown. If the synthesis requires only two steps enter "none" for step 3. OH Alcohol Starting Materials 1. methanol 2. ethanol 3. 1-propanol 4. 2-propanol 5. cyclohexanol a. LiAlH4 f. PBr3 b. H₂SO4 c. HCI d. HBr e. SOC1₂ Reagents available g. CrO3, H₂SO4, H₂O h. NaH i. CH3 MgBr; then H3O+ j. CH3 CH₂ MgBr; then H3O+ k. CH3 CH₂ CH₂ MgBr; then H3O+ I. C6H5 MgBr (phenylmagnesium bromide); then H3O+ m. (CH3)2 CHMgBr: then H3O+ n. Dess-Martin periodinane (DMP) Write the number/letters of the alchol/reagents in the boxes below. Alcohol starting material 4 Reagent for step 1 n Reagent for step 2 j Reagent for step 3 carrow_forwardSpecify both the alcohol starting material and the reagents you would use in each step in a synthesis of the compound shown. If the synthesis requires only two steps enter "none" for step 3. ů Alcohol Starting Materials 1. methanol 2. ethanol 3. 1-propanol 4. 2-propanol 5. cyclohexanol a. LiAlH4 f. PBr3 b. H₂SO4 c. HCI d. HBr e. SOC12 g. CrO3, H₂SO4, H₂O h. NaH Reagents available i. CH3 MgBr; then H3O+ j. CH3 CH₂ MgBr; then H3O+ k. CH3 CH₂ CH₂ MgBr; then H30+ I. C6H5 Mg Br (phenylmagnesium bromide); then H3O+ m. (CH3)2 CHMgBr: then H3O+ n. Dess-Martin periodinane (DMP) Write the number/letters of the alchol/reagents in the boxes below. Alcohol starting material | Reagent for step 1 Reagent for step 2 Reagent for step 3arrow_forward
- cis-Cyclohexane-1,2-diol can be synthesized from cyclohexene by using which reagent? a.O3 b.OsO4 c.H2SO4 d.mCPBAarrow_forwardThese reagents can produce ketones with alkynes A. BH3, THF, H2O2 B. KMnO4 C. O3 D. H2SO4, H2O, HgSO4arrow_forwardWrite the number/letters of the alchol/reagents in the boxes below. Alcohol starting material Reagent for step 1 Reagent for step 2 Reagent for step 3arrow_forward
- 5. Show how the following alcohol can be synthesized. a) 2-methyl butanol from suitable Grignard reagent b) cyclohexanol from chlorocyclohexane c) cylopentanol from cyclopentenearrow_forwardSpecify both the alcohol starting material and the reagents you would use in each step in a synthesis of the compound shown. If the synthesis requires only two steps enter "none" for step 3. Br Alcohol Starting Materials 1. methanol 2. ethanol 3. 1-propanol 4. 2-propanol 5. cyclohexanol a. LiAlH4 b. H₂SO4 c. HCI d. HBr e. SOCI₂ Reagent for step 2 Reagent for step 3 Reagents Available f. PBr3 g. CrO3 h. NaH i. CH3MgBr j. CH3CH₂MgBr k. CH₂CH₂CH₂MgBr I. C6H5MgBr (phenylmagnesium bromide) m. (CH3)2CHMgBr pyridinium chlorochromate (PCC) Write the number/letters of the alchol/reagents in the boxes below. Alcohol starting material Reagent for step 1 Paarrow_forwardSpecify both the alcohol starting material and the reagents you would use in each step in a synthesis of the compound shown. If the synthesis requires only two steps enter "none" for step 3. Br Alcohol Starting Materials 1. methanol 2. ethanol 3. 1-propanol 4. 2-propanol 5. cyclohexanol a. LiAlH4 f. PBr3 b. H₂SO4 c. HCI d. HBr e. SOCI₂ g. CrO3, H₂ SO4, H₂O h. NaH Reagents available i. CH3 MgBr; then H3O+ j. CH3 CH₂ MgBr; then H3O+ k. CH3 CH₂ CH₂MgBr; then H3O+ I. C6H5 MgBr (phenylmagnesium bromide); then H3O+ m. (CH3)2 CHMgBr: then H3O+ n. Dess-Martin periodinane (DMP) Write the number/letters of the alchol/reagents in the boxes below. Alcohol starting material Reagent for step 1 Reagent for step 2 Reagent for step 3arrow_forward
- Specify both the alcohol starting material and the reagents you would use in each step in a synthesis of the compound shown. If the synthesis requires only two steps enter "none" for step 3. OH Alcohol Starting Materials 1. methanol 2. ethanol 3. 1-propanol 4. 2-propanol 5. cyclohexanol Reagents available a. LiAlH4 f. PBr3 k. CH3 CH₂ CH₂ MgBr; then H3O+ b. H₂SO4 9. CrO3, H₂SO4, H₂O I. CGH, MgBr (phenylmagnesium bromide); then H3O+ c. HC1 h. NaH m. (CH3)2 CHMgBr: then H₂O+ d. HBr i. CH, MgBr; then H3O+ n. Dess-Martin periodinane (DMP) e. SOCI₂ j. CH3 CH₂ MgBr; then H3O+ Write the number/letters of the alchol/reagents in the boxes below. Alcohol starting material Reagent for step 1 Reagent for step 2 Reagent for step 3arrow_forward1. The alkene mixture obtained on dehydration of 2,2-dimethylcyclohexanol contains a significant amount of 1,2-dimethylcyclohexene a. Draw the structure of 1,2-dimethylcyclohexene b. Show a mechanism for the formation of this alkene product c. Draw the structures and give the names of any other alkene products, explaining how they could arise from the dehydration reactionarrow_forwardSpecify both the alcohol starting material and the reagents you would use in each step in a synthesis of the compound shown. If the synthesis requires only two steps enter "none" for step 3. Br Alcohol Starting Materials 1. methanol 2. ethanol 3. 1-propanol 4. 2-propanol 5. cyclohexanol Reagents available a. LIAIH4 f. PBrs k. CH3 CH2 CH, MgBr; then H30+ b. H2 SO4 g. CrO3, H2 SO4, H2O 1. C3 H5 MgBr (phenylmagnesium bromide); then H3O* с. НСI h. NaH m. (CH3)2 CHMgBr: then H30+ d. HBr i. CH;MgBr; then H30+ n. Dess-Martin periodinane (DMP) e. SOCI, j. CH3 CH2 MgBr; then H3O+ Write the number/letters of the alchol/reagents in the boxes below. Alcohol starting material Previous Nextarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
Alcohols, Ethers, and Epoxides: Crash Course Organic Chemistry #24; Author: Crash Course;https://www.youtube.com/watch?v=j04zMFwDeDU;License: Standard YouTube License, CC-BY