Interpretation:
Using the resonance structures of the intermediates the observation that the electrophilic substitution of 3-phenylpropanenitrile occurs at ortho and para positions, but reaction with 3-phenylpropenenitrile occurs at the meta position is to be explained.
Concept introduction:
In
To explain:
Using the resonance structures of the intermediates, the observation that the electrophilic substitution of 3-phenylpropanenitrile occurs at ortho and para positions, but reaction with 3-phenylpropenenitrile occurs at the meta position is to be explained.
Trending nowThis is a popular solution!
Chapter 16 Solutions
Organic Chemistry
- Several diamines are building blocks for the synthesis of pharmaceuticals and agro-chemicals. Show how both 1,3-propanediamine and 1,4-butanediamine can be prepared from acrylonitrile.arrow_forwardDefine Enamine Formation from an Aldehyde or a Ketone ?arrow_forwardReaction with 2,4-dinitrophenylhydrazine; Write whether the following aldehydes and ketones are positive or negative with 2,4-dinitrophenylhydrazine. Benzaldehyde Methyl ethyl ketone (Unknown) Acetophenonearrow_forward
- write the mechanism for a decarboxylation and state the structural features necessary for a decarboxylation.arrow_forward1. Indicate the product(s) of each of the following reactions (draw the structure):arrow_forwardThe analgesic Tylenol is often taken by people who are allergic to aspirin. Tylenol contains acetaminophen (structure shown) as the active ingredient. Is the structure of acetaminophen similar to the structure of aspirin? In what way? Would acetaminophen give a positive phenol test? What products would be obtained if acetaminophen were hydrolyzed in acidic aqueous solution?arrow_forward
- H NH₂ ཡིནྣཾ ༥ ཨ ཨནྡྷ༥ ༠ ཨི་ཝཱ, ཙ ཨ་ར༩ H NH3+ the acidity of the amine ion drives the reaction to shift toward the conjugate base of the carboxylic acid product. the resulting carboxylic acid ion is a weaker base than an acetate ion. O aldehydes are more reactive toward nucleophiles than ketones. Onucleophilic attack occurs preferentially at the less hindered carbon of the formyl group.arrow_forwardKetones and aldehydes react with sodium acetylide (the sodium salt of acetylene) to give alcohols, as shown in the following example: R1 ОН 1. НС—с: Na* R2 R1 R2 2. Нзо" HC Draw the structure of the major reaction product when the following compound reacts with sodium acetylide, assuming that the reaction takes preferentially from the Si face of the carbonyl group. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • You do not have to explicitly draw H atoms. • If a group is achiral, do not use wedged or hashed bonds on it. CH3 CHarrow_forwardConsider the following compounds that vary from nearly nonacidic to strongly acidic. Draw the conjugate bases of these compounds, and explain why the acidity increases so dramatically with substitution by nitro groups.refer to the photoarrow_forward
- A student is given a mixture of benzoic acid, 3-nitroaniline acid and naphthalene to separate. The student dissolves the mixture in an organic solvent and adds HCl to the solution. Two layers form. Which component(s) of the mixture remain in the organic solvent? Group of answer choices -naphthalene and benzoic acid -benzoic acid and 3-nitroaniline -naphthalene and 3-nitroaniline -naphthalenearrow_forward4) Rank the following compounds in order of increasing reactivity (least to most reactive) with respect to acyl substitution. I. methyl benzoate II. benzoylchloride III. benzamide III < | < ||arrow_forwardb) The Wolf-Kishner reduction is a reaction used in Organic Chemistry to convert carbonyl functionalities into methylene group. The reaction was used to convert an aldehyde or ketone to an alkane using hydrazine, base and thermal conditions. The mechanism begins with the attack of hydrazine of the aldehyde or ketone. Stage 1: The reaction of aldehyde/ketone with hydrazine to produce hydrazine Stage 2: Reaction with the base and heat to convert hydrozone to alkane Write the mechanism of the reaction.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning