
Concept explainers
Interpretation:
The resonance structure for the anion of acetonitrile, which is more acidic than ethane, is to be written and step-by-step mechanism for the condensation of benzaldehyde with acetonitrile is to be given.
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 Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a
舧 Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.
舧 Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.
舧 In nitrile, alpha hydrogen is weakly acidic, so the nitrile undergoes aldol-type condensation.
舧 A carbon-carbon bond formation occurs by aldol addition and aldol condensation reaction.
舧 An aldol reaction takes place by acid catalysis, and direct dehydration of
舧 A
舧 A chemical reaction that is catalyzed by a base is called base-catalyzed reaction.
舧 Aldol reaction is preferred in basic condition over acidic condition as after the aldol condensation, acid catalysis promotes the reaction further.
舧 An aldol reaction takes place in a protic solvent with a base.
舧 Dehydration of aldol addition product leads to the formation of conjugated
The rules for drawing resonance structures are as follows:
舧 Only nonbonding 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 solution
Chapter 19 Solutions
Organic Chemistry
- First image: I have to show the mecanism for the reaction on the left, where the alcohol A is added fast in one portion Second image: I have to show the mecanism of the reaction at the bottom. Also I have to show by mecanism why the reaction wouldn't work if the alcohol was primaryarrow_forwardFirst image: I have to explain why the molecule C is never formed in those conditions. Second image: I have to propose a synthesis for the lactone Aarrow_forwardFirst image: I have to explain why the molecule C is never formed in these conditions Second image: I have to propose a synthesis for the lactone Aarrow_forward
- help 20arrow_forwardProvide the drawing of the unknown structure that corresponds with this data.arrow_forward20.44 The Diels-Alder reaction is not limited to making six-membered rings with only car- bon atoms. Predict the products of the following reactions that produce rings with atoms other than carbon in them. OCCH OCCH H (b) CH C(CH₂)s COOCH མ་ནས་བ (c) N=C H -0.X- (e) H C=N COOCHS + CH2=CHCH₂ →→arrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples 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 EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY





