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 11.14, Problem 11.37P
To practice working through the early parts of a multistep synthesis, devise syntheses of
- a. pentan-3-one from alcohols containing no more than three carbon atoms.
- b. 3-ethylpentan-2-one from compounds containing no more than three carbon atoms.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
For each reaction identify the reaction type.
Reaction
Туре
a. Methylbenzene and bromine in the presence of ultraviolet light forming 1-
bromo-2-methylbenzene and hydrogen bromide.
b. 2-methyldecane plus hydrogen reacts to produce heptane and butane
c. Hex-2-ene plus hydrogen chloride produces 2-chlorohexane.
d. Propane plus pentane reacts to produce 1,2-dimethylcyclohexane and
hydrogen
Provide the major organic product for the
1. LilH
4
2.нсін, о
Provide the major organic product of the
following reaction.
following reaction. ?.
6. Provide the major organic product for the following reaction.
HO
Br
OH
NH
-
Br
1. LIAIH4
2. HC1, H₂O
7. Provide the major organic product of the following reaction.
concentrated KMnO4
reflux
6- Prepare cis-2-butane using propyne, and alkyl halide. Use any other reagents needed.7- Use 4-Octene as the only source of carbon in the synthesis of Butanal. Use anyinorganic compounds necessary.
Chapter 11 Solutions
Organic Chemistry (9th Edition)
Ch. 11.1 - Prob. 11.1PCh. 11.2C - Prob. 11.2PCh. 11.3 - Prob. 11.3PCh. 11.3 - Prob. 11.4PCh. 11.3 - Prob. 11.5PCh. 11.3 - Suggest the most appropriate method for each of...Ch. 11.4 - A chronic alcoholic requires a much larger dose of...Ch. 11.4 - Unlike ethylene glycol, propylene glycol...Ch. 11.5 - Predict the major products of the following...Ch. 11.5 - Show how you would convert propan-1-ol to the...
Ch. 11.6 - Predict the products of the following reactions....Ch. 11.7A - Propose a mechanism for the reaction of a....Ch. 11.7B - Prob. 11.13PCh. 11.7B - Show how you would use a simple chemical test to...Ch. 11.7C - Neopentyl alcohol, (CH3)3CCH2OH, reacts with...Ch. 11.7C - Prob. 11.16PCh. 11.7C - When cis-2-methylcyclohexanol reacts with the...Ch. 11.8 - Prob. 11.18PCh. 11.9 - Prob. 11.19PCh. 11.9 - Prob. 11.20PCh. 11.9 - Prob. 11.21PCh. 11.10A - Prob. 11.22PCh. 11.10A - Some alcohols undergo rearrangement or other...Ch. 11.10B - Prob. 11.24PCh. 11.10B - Explain why the acid-catalyzed condensation is a...Ch. 11.10B - Prob. 11.26PCh. 11.10B - When the following substituted cycloheptanol...Ch. 11.11A - Prob. 11.28PCh. 11.11A - Prob. 11.29PCh. 11.11B - Predict the products formed by periodic acid...Ch. 11.12 - Prob. 11.31PCh. 11.13A - Prob. 11.32PCh. 11.14 - Prob. 11.33PCh. 11.14 - a. Show how ethanol and cyclohexanol may be used...Ch. 11.14 - Prob. 11.35PCh. 11.14 - Phenols (pKa 10) are more acidic than other...Ch. 11.14 - To practice working through the early parts of a...Ch. 11.14 - Prob. 11.38PCh. 11 - Predict the major products of the following...Ch. 11 - Show how you would convert 2-methylcyclopentanol...Ch. 11 - In each case, show how you would synthesize the...Ch. 11 - Prob. 11.42SPCh. 11 - Prob. 11.43SPCh. 11 - Prob. 11.44SPCh. 11 - Both cis- and trans-2-methylcyclohexanol undergo...Ch. 11 - Prob. 11.46SPCh. 11 - Prob. 11.47SPCh. 11 - Show how you would make each compound, beginning...Ch. 11 - Predict the major products (including...Ch. 11 - Show how you would use simple chemical tests to...Ch. 11 - The compound shown below has three different types...Ch. 11 - Prob. 11.52SPCh. 11 - Prob. 11.53SPCh. 11 - Prob. 11.54SPCh. 11 - Prob. 11.55SPCh. 11 - Show how you would synthesize the following...Ch. 11 - Show how you would synthesize the following...Ch. 11 - The following pseudo-syntheses (guaranteed not to...Ch. 11 - Two unknowns, X and Y, both having the molecular...Ch. 11 - The Williamson ether synthesis involves the...Ch. 11 - Prob. 11.61SPCh. 11 - Prob. 11.62SPCh. 11 - Alcohols combine with ketones and aldehydes to...Ch. 11 - Prob. 11.64SPCh. 11 - Prob. 11.65SPCh. 11 - Prob. 11.66SP
Additional Science Textbook Solutions
Find more solutions based on key concepts
Which of the following solutions has the higher molarity? 10 ppm KI in water or 10,000 ppb KBr in water 0.25 ma...
CHEMISTRY-TEXT
The structural formula of 1, 2-dimethylbenzene needs to be drawn. Concept introduction: The ring structures of ...
Chemistry: Matter and Change
Q1. What is the empirical formula of a compound with the molecular formula
Chemistry: A Molecular Approach (4th Edition)
Practice Problem 1.22 Which of the following alkenes can exist as cis-trans isomers? Write their structures. Bu...
Organic Chemistry
Calculate the lattice energy of CaCl2 using a Born-Haber cycle and data from Appendices F and L and Table 7.5. ...
Chemistry & Chemical Reactivity
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
- 4. Which synthesis, starting from benzene, forms aniline (aminobenzene)? a. 1) HNO3/H₂SO4 b. 1) HNO3/H₂SO4 2) H₂, Pd/C c. 1) NH₂/H₂SO4 d. 1) Cl2, FeCl3 2) NaOH, high T,P e. 1) NH₁/H₂SO4 2) H₂, Pd/Carrow_forwardOxidation of Butanol -1 in KMnO4/H+ will produce-------------. a.Butanoic Acid b.Butanal c.Pentanoic acid d.Butene -2arrow_forwardEvaluate the chemical reactions carefully. Predict the reagents required (marked with letters) in order to satisfy the given reactions. A.) Synthesis of 4-octanol Aarrow_forward
- Write the structural formula of the organic product for the given reaction between an alkyne and an alkyl halide. The alkyne group is shown and should be entered as "CC" without the triple bond. Enter CC before associated HH atoms (e.g., CH3CH2CH2OCHCHCH3). what is the name of the product. 1.NaNH2 CH3CH2CCH------> product 2. CH3CH2Brarrow_forwardTo practice working through the early parts of a multistep synthesis, devise syntheses of pentan-3-one from alcohols containing no more than three carbon atomsarrow_forwardChoose the two alkyl bromides and the hydrogenation method that must be used to synthesize these alkenes from acetylene. Enter your answer as two letters in alphabetical order, followed by a number; i.e. ac2, not ca2. Do not use punctuation. Alkyl Halides a. CH3CH,Br. b. CH3(CH2)4Br c. CH3(CH2);Br d. CH3(CH2)6Br e. CH3(CH2);Br f. CH3(CH2);Br g. CH3(CH2)12B Hydrogenation Method 1. H2, Lindlar's catalyst 2. Na, NH3 (1) Alkene #1: H3C CH3 Alkene #2: CH3 H3Carrow_forward
- 1. 2-bromobutane + cyclohexanol + NaH à (major product) c. 2-butoxycyclohexane a.. 2-butene reaction b. 1-butene d. no e. something else! 2. t-butylbromide + sodium ethoxide in ethanol à (major product) a. 2-methylpropene reaction b. t-butyl ethyl ether c. 1-methylbutene d. no e. something else! 3. potassium t-butoxide + 1-bromobutane in t-butyl alcohol room temperature à (major product) a. 1-butene reaction c. 2-methylpropene d. no b. butyl t-butyl ether e. something else! 4. t-butyl bromide + boiling hot water à (major product) a. 2-methylpropene reaction b. t-butyl ethyl ether c. t-butanol d. no e. something else! 5. 2-chloropropane + acetic acid (2 eq) / KOH (1 eq) / DMF à(major product) c. b. d. no reaction e. something а. HO. else! Br KOH / DMSO 6. b. 2-methyl-1-propanol d. 1,2- a. 2-methylpropene propanediene c. no reaction e. something else! 7. cyclopentanol+ NaH + DMSO + bromopropane à(major product) a. cyclopentene reaction b. propene e. something else!! c. propyl cyclopentyl…arrow_forwardDraw the structure(s) of the major organic product(s) of the following reaction. 1. KMno, / aq. NaOH H. 2. aqueous H,S0. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • If no reaction occurs, draw the organic starting material. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple products using the + sign from the drop-down menu. C opy aste C. [F ChemDoodlearrow_forwardByphenyl synthesis. From benzene, organic compounds with 2 carbons or less, and any other inorganic compound you want. Synthesize the following molecule.arrow_forward
- Select an appropriate synthetic route for the equation given. A acetylene 1. NaNH₂; 2. CH3Br; 3. NaNH2; 4. CH3Br; 5. H₂, Lindlar's catalyst; 6. H3O+ 1. NaNH2; 2. CH3Br; 3. NaNH2; 4. CH3Br; 5. H2, Lindlar's catalyst; 6. RCO3H 1. NaNH2; 2. CCH3. NaNH2;4. CH3Br; 5. H2, Pd; 6. RCO3H 1. NaNH2; 2. CCl4; 3. NaNH2; 4. CH3Br; 5. Hz, Lindlar's catalyst; 6. RCOSH 1. NaNH2; 2. CH3Br; 3. NaNH2; 4, CHgBr; 5. Hz. Pt; 6. RCO3Harrow_forwardBy means of a series of equations outline a method for carrying out the ff. conversions. You may use reagents you wish. More than one step maybe required. a. acetylene b. cyclohexanone c. ethyl bromide d. benzene athanol +methylcyclohexanol acetaldehyde +phenyl ethanol B-ethyl-3-pentanol tyclopentanone 2-суano-2-pentanol benzyl alcohol 2-butanone-semicarbazone е. 3-рentanol f. cyclopentene g. 2-pentanol h. benzene i. 2-butanolarrow_forward4. Illustrate the formation of the Acyl Halide Chlorobenzyl and its byproducts from the reaction of Benzoic acid with phosphorus pentachloride. Instruction: a.) Write the Correct Structural Formula of the Reactant/s b.) Write the formula of the specific Catalyst/s of the reaction c.) Predict the Product/s of the given reactions.arrow_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