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
Videos
Textbook Question
Chapter 9.7A, Problem 9.7P
Show how you might synthesize the following compounds, using acetylene and any suitable
- a. hex-1-yne
- b. hex-2-yne
- c. hex-3-yne
- d. 4-methylhex-2-yne
- e. 5-methylhex-2-yne
- f. cyclodecyne
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
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
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…
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
Chapter 9 Solutions
Organic Chemistry (9th Edition)
Ch. 9.1 - a. Count the elements of unsaturation in...Ch. 9.2 - Prob. 9.2PCh. 9.4B - What reaction would acetylene likely undergo if it...Ch. 9.6 - Prob. 9.4PCh. 9.6 - Predict the products of the following acid-base...Ch. 9.7A - Solved Problem9-1 showed the synthesis of...Ch. 9.7A - Show how you might synthesize the following...Ch. 9.7B - Prob. 9.8PCh. 9.7B - Show how you would synthesize...Ch. 9.8 - When 2,2-dibromo-1-phenylpropane is heated...
Ch. 9.8 - When 2,2-dibromo-1-phenylpropane is heated...Ch. 9.9C - Show how you would convert a. oct-3-yne to...Ch. 9.9C - The fragrance of (Z)-1-phenylhex-2-en-1-ol...Ch. 9.9D - In the addition of just 1 mole of bromine to 1...Ch. 9.9E - Propose a mechanism for the entire reaction of...Ch. 9.9E - Predict the major product(s) of the following...Ch. 9.9E - Propose a mechanism for the reaction of pent-1-yne...Ch. 9.9E - Show how hex-1-yne might be converted to a....Ch. 9.9F - When pent-2-yne reacts with mercuric sulfate in...Ch. 9.9F - Prob. 9.20PCh. 9.9F - Prob. 9.21PCh. 9.9F - Prob. 9.22PCh. 9.10A - Predict the product(s) you would expect from...Ch. 9.10B - Prob. 9.24PCh. 9.10B - Prob. 9.25PCh. 9 - Prob. 9.26SPCh. 9 - Give common names for the following compounds. a....Ch. 9 - Prob. 9.28SPCh. 9 - Prob. 9.29SPCh. 9 - Using cyclooctyne as your starting material, show...Ch. 9 - Prob. 9.31SPCh. 9 - Prob. 9.32SPCh. 9 - Predict the products of reaction of pent-1-yne...Ch. 9 - Show how you would accomplish the following...Ch. 9 - Show how you would synthesize the following...Ch. 9 - Predict the products formed when CH3CH2C C : Na+...Ch. 9 - Prob. 9.37SPCh. 9 - Prob. 9.38SPCh. 9 - When compound Z is treated with ozone, followed by...Ch. 9 - Show how you would convert the following starting...Ch. 9 - The following functional-group interchange is a...Ch. 9 - Using any necessary inorganic reagents, show how...Ch. 9 - Prob. 9.43SP
Additional Science Textbook Solutions
Find more solutions based on key concepts
Why are mutants used as test organisms in the Ames test?
Laboratory Experiments in Microbiology (12th Edition) (What's New in Microbiology)
To test your knowledge, discuss the following topics with a study partner or in writing ideally from memory. Th...
HUMAN ANATOMY
Choose the best answer to each of the following. Explain your reasoning. If Earth were twice as far as it actua...
Cosmic Perspective Fundamentals
Gregor Mendel never saw a gene, yet he concluded that some inherited factors were responsible for the patterns ...
Campbell Essential Biology (7th Edition)
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
- Show how to convert propene to each of these compounds, using any inorganic reagents as necessary. a. Propane b.1,2-Propanediol c. 1-Propanol d. 2-Propanol e. Propanal f. Propanone g. Propanoic acid h. l-Bromo-2-propanol i. 3-Chloropropene j. 1,2,3-Trichloropropane k. 1-Chloropropane l. 2-Chloropropane m. 2-Propen-1-ol n. Propenalarrow_forwardBy means of a series of equations outline a method for carrying out the ff. conversions. You may use any reagents you wish. More than one step maybe required.arrow_forwardStarting Materials CH3B CH3CH2BR CH3CH2CH,Br C6H5Br Reagents Mg, ether 1. a. 2. 13CH2-13C-OH b. 13CO2 then H3O* 3. LIAIH4 then H3o* PBr3 CO2 then H30* C. 4. d. 5. C6HsCH2Br е. Select a starting material and a series of reagents necessary to synthesize this compound in as few steps as possible. Enter your selection as a number for the starting material, followed by the letters of the reagents, in the order that you wish to use them, i.e. 3abcf.arrow_forward
- 22. Which of the following hydrocarbons requires 2 moles of Br2? A. 1-butene B. 1-butyne C. 1,3-butadiene D. B and C 23. Which of the following generates the most stable carbonium ion? A. Methyl carbonium ion B. tertiary carbonium ion C. allyl carbonium ion D. ethyl carbonium ion 24. If the reaction below is conducted under kinetic controlled conditions, which is the major product? 20=20 toarrow_forward2. Name each alkyne. a. CH3CH₂CH₂C=CH b. CH3CH₂CH₂C=CCH3 3. Predict the product of the following reactions. a. CH = CCH3 + HCI b. CH CCH₂CH3 + O2arrow_forward19. Complete the following reactions. a. CH3CH=CHCH3 + H2 C. + Cl₂ FeC 13. Pt CH₂=CHCHCH=CH + 2C12 нансност CH 3 b. d. CH3 CH3C=CH₂ CH3 + 02 sparkarrow_forward
- Which reagent is appropriate for the following reaction. Cyclohexene converted to trans-cyclohexane diol. A. KMNO4, cold, neutral B. 1. OsO4/2. NaHSO3, H2O С. 1. RCOOОН/2. ОН- D. HIO4arrow_forwardI’m bad at nomenclature I would be glad if you helped me.arrow_forward1. What alkene will produce the HIGHEST yield of the alkyl halide below? 2. Which of the following alkynes can be deprotonated by NaNH2 in liquid NH3? a. Pent-2-yne b. Hex-3-yne c. none of these d. 3-Methylbutyne e. 3-Methylhex-2-ynearrow_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 Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles 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 Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary 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
IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY