ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
12th Edition
ISBN: 9781119304241
Author: Solomons
Publisher: WILEY C
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Chapter 7, Problem 2PP
Interpretation Introduction
Interpretation:
The given cycloalkene is to be ranked in order of increasing stability.
Concept introduction:
The stability of an
The stability of alkene increases as the number of alkyl groups attached to the carbon atom of the double bond increases.
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Students have asked these similar questions
(B) Draw two chair conformations of the following substituted cyclohexane and identify the
most stable conformation. Clearly show the axial and equatorial bonds.
7.40
a. Suggest an explanation for the fact that 1-methylcyclopropene is some 42 kJ/mol (10 kcal/mol) less stable
than methylenecyclopropane.
-CH3
is less stable than
CH2
1-Methylcyclopropene
Methylenecyclopropane
b. On the basis of your answer to part (a), compare the expected stability of 3-methylcyclopropene with that
of 1-methylcyclopropene and that of methylenecyclopropane.
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)
Chapter 7 Solutions
ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
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
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- For each alkene, indicate the direction of the dipole moment. For each pair, determine which compound has the largerdipole moment.(a) cis-1,2-difluoroethene or trans-1,2-difluoroethene(b) cis-1,2-dibromoethene or trans-2,3-dibromobut-2-enearrow_forward5.47 Show how to convert methylenecyclohexane into each of these compounds. -CH2OH (a) OH (b) ECH2 CH3 (c) Methylenecyclohexanearrow_forward2.35 Write a structural formula for each of the following compounds: (a) 6-Isopropyl-2,3-dimethylnonane (b) 4-tert-Butyl-3-methylheptane (c) 4-Isobutyl-1,1-dimethylcyclohexane (d) sec-Butylcycloheptane (e) Cyclobutylcyclopentanearrow_forwardDerive 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 Xarrow_forwardProvide an IUPAC name for each of the compounds shown. (Specify (E) (Z) stereochemistry, if relevant, for straight chain alkenes only. Pay attention to commas, dashes, etc.) CH3CH2CH2CH2 CH3 H3CH2C CH2CH3 H3C CH3 CH3arrow_forwardDehydrohalogenation of 1-chloro-1-methylcyclopropane affords two alkenes (A and B) as products. Explain why A is the major product despite the fact that it contains the less substituted double bond.arrow_forwardProvide an IUPAC name for each of the compounds shown. (Specify (E)/(Z) stereochemistry, if relevant, for straight chain alkenes only. Pay attention to commas, dashes, etc.) Br. H C=C CH3 H₂C-CH₂ CI CH₂CH3arrow_forwardUsing cyclohexane as your starting material, show how you would synthesize each of the following compounds. (Onceyou have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)(a) bromocyclohexane (b) cyclohexenearrow_forwardThere are three diastereomers of 2-bromo-1,3-dimethylcyclohexane. (a) Using the orientation of the chair conformation shown below, draw all three diastereomers of 2-bromo-1,3-dimethyleyclohexane. Follow the numbering given when placing the positions of the two methyl groups and make sure that the bromine leaving group remains in the axial position as shown. 1 2 3 Br Diastereomer 1 Diastereomer 2 Diastereomer 3 (b) Only 2 of these diastereomers undergo an E2 reaction with HO-. Based on the nature of the required transition states for E2 reactions, indicate with an asterisks *, which of the ones you drew in part (a) above undergoes an E2 reaction? (c) The diastereomer that does not undergo an E2 reaction, reacts with HO to form the SN2 product instead. Draw the structure of this SN2 product.arrow_forwardGive the IUPAC name for each of the following compounds in the corresponding box. Please apply E/Z or cis/trans accordinglyarrow_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_forwardarrow_back_iosSEE MORE QUESTIONSarrow_forward_ios
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