Concept explainers
Interpretation:
The reason behind hydrogens attached to third carbon in 1,4-pentadiene being more susceptible to abstraction by radicals is to be explained. Also, the reason behind hydrogens attached to third carbon in 1,4-pentadiene being more acidic than hydrogens attached to methyl group of propene is to be explained.
Concept introduction:
舧 Electrophiles are electron-deficient species, which has positive or partially positive charge. Lewis acids are electrophiles, which accept electron pair.
舧 Nucleophiles are electron-rich species, which has negative or partially negative charge. Lewis bases are nucleophiles, which donate electron pair.
舧 Free radical is an atom, molecule, or ion that has an unpaired electron, which makes it highly chemically reactive.
舧 Conjugated systems consist of a phenomenon known as conjugation, which can be defined as an interaction between p-orbitals with another across an intervening sigma bond. Conjugated systems, in simple words, can be represented as a system in organic compounds having alternate double bonds and single bonds.
舧 Delocalization of unpaired electrons results in more stability. Alkyl groups attached to the carbon atom having the positive charge or radical, helps in more stabilization of charge. Thus, tertiary carbocations or radicals are more stable than secondary and secondary carbocations are more stable than primary carbocations or radicals.
舧 Resonance is having 2 different shapes of a chemical entity but the change is only in the electron pair positions.
舧 Resonance enhances the acidity of the compound and makes it easier for the compound to give up protons. Higher resonant structures increase acidity of the compound.
The rules for drawing resonance structures are as follows:
舧 Only non-bonding electron pairs and pi electrons can participate in conjugation in the formation of various resonating structures.
舧 The single bonds present in the molecule do not break or form in the resonance structures.
舧 The placement of atoms present in the molecule remains fixed.
舧 The octet of all atoms is completely filled.
舧 More the number of resonance structures indicate higher stability of a compound.
Want to see the full answer?
Check out a sample textbook solutionChapter 13 Solutions
Organic Chemistry
- Methyl acrylate (H2C=CHCO2CH3) reacts with 1,3-cyclopentadiene to give a mixture of two products. Write structural formulas for both and predict which one predominates.arrow_forwardCalculate the units of unsaturation of C6H7NO. And draw out the structure.arrow_forwardThere are two alkenes that react with HBr to give 1-bromo-1-methylcyclohexane. Draw their structures.arrow_forward
- (a) Describe the molecular geometry expected for 1,2,3-butatriene (H2C=C=C=CH2). (b) Two stereoisomers are expected for 2,3,4-hexatriene (CH3CH=C=C=CHCH3). What should be the relationship between these two stereoisomers?arrow_forwardCompound A, C4H40, undergoes the ring substitution reactions characteristic of aromatics to give two isomers. Draw the structure of A. ring substitution 2 substitution isomers A Draw cations and anions in separate sketchers. • Separate structures with + signs from the drop-down menu. ChemDoodlearrow_forwardCompound A (C6H14) forms three different monochlorides by photochemical chlorination. One of these monochlorides is inert to E2 elimination. The other two monochlorides produce the same alkene B (C6H12) when heated with potassium tert-butoxide in tert-butyl alcohol.Identify compound A, the three monochlorides, and alkene B.arrow_forward
- Describe a sequence of reactions by which cis-2-pentene could be prepared from acetylene.arrow_forwardThe reaction of Hbr with 2-methylpropene produces 2-bromo-2-methylpropane. What is the structure of the carbocation formed during the reaction?arrow_forwardCompound A(C7H15Br) is not a primary alkyl bromide. It yields a single alkene(compound B) on being heated with sodium ethoxide in ethanol. Hydrogenation of compound B yields 2,4-dimethylpentane. Identify compounds A and B.arrow_forward
- Oropheic acid is the common name of a naturally occurring acetylenic carboxylic acid having the molecular formula C18H22O2. Its systematic name is 17-octadecene-9,11,13-triynoic acid. What is its structural formula?arrow_forwardAcridine is a heterocyclic aromatic compound obtained from coal tar that is used in the synthesis of dyes. The molecular formula of acridine is C13H9N, and its ring system is analogous to that of anthracene except that one CH group has been replaced by N. The two most stable resonance structures of acridine are equivalent to each other, and both contain a pyridine-like structural unit. Write a structural formula for acridine.arrow_forwardA compound with formula C7H12O is treated with sodium borohydride in methanol to yield 2,2-dimethylcylopentanol. Write a reaction scheme showing the structures of the reactant, the reagents, and the product. Will the product be optically active? Explain.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningMacroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole