Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 7, Problem 48P
Interpretation Introduction

Interpretation:

The synthesis of the given compounds starting from ethyne is to be outlined.

Concept introduction:

Electrophiles are electron-deficient species, which has positive or partially positive charge. Lewis acids are electrophiles, which accept electron pair.

Nucleophiles are electron-rich species, which has negative or partially negative charge. Lewis bases are nucleophiles, which donate electron pair.

Nucleophilic substitution reaction is a reaction in which an electron-rich nucleophile attacks the positive or partial positive charge of an atom or a group of atoms to replace a leaving group.

The acid catalyzed dehydration is a reaction in which alcohol is converted into alkene.

Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.

Nucleophilic substitution reaction: A reaction in which one of the hydrogens of a hydrocarbon or a functional group is substituted by any nucleophile is called substitution reaction.

A nucleophile is a molecule or atom with most negative charge.

There are two types of nucleophilic substitution reactions: SN1, which is a unimolecular reaction and SN2, which is a bimolecular reaction.

The reaction in which the halide group is removed to form an alkene is called dehydrohalogenation.

The compounds that have the same molecular formula of atoms but the structure of the compounds are different for the positions of atoms are called isomers.

In double bond or cyclic compounds, if two same functional groups are present on the same side of the double bond or cyclic compound, the given compound can be labeled as cis.

If the two functional groups are present on the different sides of the double bond or cyclic compound, the given compound can be labeled as Trans.

Cis-trans isomerism exists in the compounds in which similar groups are present on the adjacent carbon atoms.

In alkenes, if the higher priority group on both the carbon is on the same side, configuration is termed as Z-configuration.

In alkenes, if the higher priority group on both the carbon is on the opposite side, configuration is termed as E-configuration.

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Write structural formulas for the following compounds (includes both old- and new-style names).(a) 2-octyne (b) ethylisopentylacetylene (c) ethynylbenzene(d) cyclohexylacetylene (e) 5-methyl-3-octyne (f) trans-3,5-dibromocyclodecyne(g) 5,5-dibromo-4-phenylcyclooct-1-yne (h) (E)-6-ethyloct-2-en-4-yne (i) 1,4-heptadiyne
Develop syntheses for the following compounds, using acetylene and compounds containing no more than four carbon atoms as your organic starting materials.(a) 3-methylnon-4-yn-3-ol (“3-ol” means there is an OH group on C3.)(b) cis-1-ethyl-2-methylcyclopropane
Show, by writing an appropriate series of equations, how you could prepare propyne from each of the following compounds as starting materials. You may use any necessary organic or inorganic reagents. (a) 2-Propanol (d) 1,1-Dichloroethane (b) 1-Propanol (e) Ethyl alcohol (c) Isopropyl bromide

Chapter 7 Solutions

Organic Chemistry

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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