Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 7, Problem 4PP
Interpretation Introduction
Interpretation:
For each pair, the more stable
Concept introduction:
The stability of alkene is depending on the number of alkyl group attached to the carbon atom of the double bond.
The stability of alkene increases as the number of alkyl group attached to the carbon atom of double bond increases.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Rank by the stability of the alkene isomers.
The most stable isomer is 1, while the least
stable isomer is 5.
(A)
(B)
(C)
(D)
(E)
• PRACTICE PROBLEM 8.12
Treating a hindered alkene such as 2-methyl-2-butene with BH3:THE leads to the for-
mation of a dialkylborane instead of a trialkylborane. When 2 mol of 2-methyl-2-butene
is added to 1 mol of BH3, the product formed is bis(3-methyl-2-butyl)borane, nicknamed
in
reagent
"disiamylborane." Write its structure. Bis(3-methyl-2-butyl)borane is a useful
certain syntheses that require a sterically hindered borane. (The name “disiamyl" comes
from "disecondary-iso-amyl," a completely unsystematic and unacceptable name. The
name "amyl" is an old common name for a five-carbon alkyl group.) donby
Derive an IUPAC name for the following (cyclo)alkenes.
(Do not use cis/trans in your names. Use only the (E)/(Z) designations for double bond stereochemistry. It is not necessary to use italics in writing compound names.)
(a)
(b)
my
X
Chapter 7 Solutions
Organic Chemistry
Ch. 7 - Prob. 1PPCh. 7 - Prob. 2PPCh. 7 - Prob. 3PPCh. 7 - Prob. 4PPCh. 7 - Practice Problem 7.5
How many stereoisomers are...Ch. 7 - Prob. 6PPCh. 7 - Prob. 7PPCh. 7 - PRACTICE PROBLEM 7.8
Examine Solved Problem 7.3....Ch. 7 - Prob. 9PPCh. 7 - Practice Problem 7.10 When...
Ch. 7 - Practice Problem 7.11
(a) When...Ch. 7 - Prob. 12PPCh. 7 - Prob. 13PPCh. 7 - Practice Problem 7.14
Dehydration of 2-propanol...Ch. 7 - Practice Problem 7.15
Rank the following alcohols...Ch. 7 - Practice Problem 7.16
Acid-catalyzed dehydration...Ch. 7 - Practice Problem 7.17 Acid-catalyzed dehydration...Ch. 7 - Prob. 18PPCh. 7 - Prob. 19PPCh. 7 - Practice Problem 7.20
Show how you might...Ch. 7 - Prob. 21PPCh. 7 - Prob. 22PPCh. 7 - Practice Problem 7.23
Write the structure of...Ch. 7 - Prob. 24PPCh. 7 - Prob. 25PPCh. 7 - Practice Problem 7.26 (a) Devise retrosynthetic...Ch. 7 - Each of the following names is incorrect, Give the...Ch. 7 - Prob. 28PCh. 7 - Prob. 29PCh. 7 - Give the IUPAC names for each of the following:...Ch. 7 - Prob. 31PCh. 7 - Prob. 32PCh. 7 - Prob. 33PCh. 7 - Prob. 34PCh. 7 - 7.35. Write structural formulas for all the...Ch. 7 - 7.36. Explain the following observations: When...Ch. 7 - Prob. 37PCh. 7 - Arrange the following alcohols in order of their...Ch. 7 - Prob. 39PPCh. 7 - Prob. 40PPCh. 7 - Prob. 41PPCh. 7 - Prob. 42PPCh. 7 - Your task is to prepare isopropyl methyl ether by...Ch. 7 - Prob. 44PCh. 7 - Prob. 45PCh. 7 - Prob. 46PCh. 7 - 7.47. Starting with an appropriate alkyl halide...Ch. 7 - Prob. 48PCh. 7 - 7.49. What is the index of hydrogen deficiency...Ch. 7 - Prob. 50PCh. 7 - Prob. 51PCh. 7 - Compounds I and J both have the molecular formula...Ch. 7 - Prob. 53PCh. 7 - 7.54. Outline a synthesis of phenylethyne from...Ch. 7 - Prob. 55PPCh. 7 - Prob. 56PPCh. 7 - Prob. 57PPCh. 7 - cis-4-Bromocyclohexanol tBuOHtBuO racemic C6H10O...Ch. 7 - Prob. 59PPCh. 7 - Consider the interconversion of cis-2-butene and...Ch. 7 - Prob. 61PCh. 7 - (a) Using reactions studied in this chapter, show...Ch. 7 - Prob. 63PCh. 7 - Prob. 64PCh. 7 - 1. Write the structure(s) of the major product(s)...Ch. 7 - Prob. 2LGPCh. 7 - (a) Write the structure of the product(s) formed...Ch. 7 - Prob. 4LGP
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
- 6. Which of the following substances have meso forms? Draw them. (a) 2,3-Dibromobutane (b) 2,3-Dibromopentane (c) 2,4-Dibromopentane 7. What kinds of isomers are the following pairs? (a) (S)-5-Chlorohex-2-ene and chlorocyclohexane (b) (2R,3R)-Dibromopentane and (2S,3R)-dibromopentanearrow_forwardPRACTICE PROBLEM 6.5 Using chair conformational structures (SectionA), show the nueleophilie substitution reaction that would take place when trans-1-bromo-4-tert-butyleyclohexane reacts with lodide lon. (Show the most stable conformnation of the reactant and the product.) Sy2 reactions always occur with inversion of configurationarrow_forward7.44 Give the structures of two different alkyl bromides both of which yield the indicated alkene as the exclusive product of E2 elimination. (а) СH;CH—CH, (b) (CH3)2С—СH2 (c) BRCH=CB12 CH3 (d) CH3arrow_forward
- Write the IUPAC name for each compound, including the designation of configuration. Do not worry about italics, however syntax is important. (a) Br (b) (S)-2-bromobutane Br H3C. (c) 1-bromo-4-methylcyclohexane (d) 3-chlorocyclohexenearrow_forwardO PRACTICE PROBLEM 8.14 Starting with any needed alkene (or cycloalkene) and assuming you have deuterioace- tic acid (CH3CO,D) available, outline syntheses of the following deuterium-labeled compounds.s el en olad lo nohibbs ad CH3 (a) (CH3)2CHCH2CH,D (b) (CH3),CHCHDCH3 (c) (+ enantiomer) (d) Assuming you also have available BD3:THF and CH3CO2T, can you suggest a synthesis of the following? hab erl (+ enantiomer)he imo (nwond-ben) CH3 H. (asoholea)arrow_forward5.47 Show how to convert methylenecyclohexane into each of these compounds. -CH2OH (a) OH (b) ECH2 CH3 (c) Methylenecyclohexanearrow_forward
- Compound X, C,4H12Br2, is optically inactive. On treatment with strong base, X gives hydrocarbon Y, C14H10: Compound Y absorbs 2 equivalents of hydrogen when reduced over a palladium catalyst to give z (C14H14) and reacts with ozone to give one product, benzoic acid (C,Hg02). Draw the structure of compound Z. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Ignore alkene stereochemistry. • If more than one structure fits the description, draw them all. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. ChemDoodlearrow_forward7.55 Acid-catalyzed dehydration of 2,2-dimethyl-1-hexanol gave a number of isomeric alkenes including 2- methyl-2-heptene as shown in the following equation. H2SO4 НО heat (a) Write a stepwise mechanism for the formation of 2-methyl-2-heptene, using curved arrows to show the flow of electrons. (b) What other alkenes do you think are formed in this reaction?arrow_forward4.2 10 Give the reaction mechanism showing all possible products for the following reactions: (a) Reaction of 1-propene with hydrogen bromide, HBr (g) (b) Reaction of ethene with bromine, Br₂ (1)arrow_forward
- For each pair of compounds, predict which one has the higher molecular dipole moment, and explain your reasoning.(a) cis-2,3-dibromobut-2-ene or trans-2,3-dibromobut-2-enearrow_forward2. (a) Reaction of an alkene with ozone followed by an oxidative workup gives the product shown. What is the structure of alkene A? A (b) Compounds B and C both have the formula C10H16. Hydrogenation of either compound over Pt gives the same product, cis-1-isopropyl-4-methylcyclohexane. Ozonolysis with reductive workup fragments the two compounds differently, as shown below. What are the structures of C B and C? (CHCl3, chloroform, is the solvent.) B 1) 03, CHCI 3 2) (CH3)2S 1) 03, CHC13 2) (CH3)2S H O 1) 03 2) H₂O2, H₂O H3C- H O CH3 3. (a) Draw the structures of all enols that would spontaneously form this ketone, including stereoisomers. + + I HO₂C H + La CH3CH₂-C-CH(CH3)2 O= (b) Would alkyne hydration be a good preparative method for this compound? If so, give the reaction. If not, explain why.arrow_forwardProvide the IUPAC name for each of the following compounds. Pay close attention to stereochemistry. (a) (b) -NH2 (c) OH ОН NH2 NH2 НО .CI Br. NH2 O,N"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 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