Concept explainers
(a)
Interpretation:
A mechanism for the first step of the given reaction has to be given.
Concept Introduction:
Grignard Reaction: This is a organometallic reaction in different alkyl, aryl-magnesium halides add to a carbonyl group in an
Alkyl or aryl magnesium halides (
Synthesis of Grignard reagent is shown below,
Nucleophiles: A nucleophile is a more reactant species that affords a pair of electrons to the electrophile or electrophilic center and forms a new covalent bond. The carbon or other hetero atom in a molecule which is bearing negative charge or lone pair of electron is called as nucleophiles.
(b)
Interpretation:
The function of the acid in the second step for given reaction has to be explained.
Concept Introduction:
Grignard Reaction: This is a organometallic reaction in different alkyl, aryl-magnesium halides add to a carbonyl group in an aldehyde and ketone. This reaction is an important for the conversion of carbon-carbon single
Alkyl or aryl magnesium halides (
Synthesis of Grignard reagent is shown below,
Nucleophiles: A nucleophile is a more reactant species that affords a pair of electrons to the electrophile or electrophilic center and forms a new covalent bond. The carbon or other hetero atom in a molecule which is bearing negative charge or lone pair of electron is called as nucleophiles.
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Chapter 15 Solutions
Organic Chemistry
- (a) Explain the mechanism of a nucleophilic attack on the carbonyl group of an aldehyde or a ketone.(b) An organic compound (A) (molecular formula CgH16Q2) was hydrolysed with dilute sulphuric acid to give a carboxylic acid (B) and an alcohol (C). Oxidation of (C) with chromic acid also produced (B). On dehydration (C) gives but-1-ene. Write the equations for the reactions involved.arrow_forwardWhen ethyl bromide is added to potassium tert-butoxide, the product is ethyl tert-butyl ether.(a) What happens to the reaction rate if the concentration of ethyl bromide is doubled?arrow_forwardThe hydrocarbon fluorene was treated with potassium t-butoxide in an acid-base reaction, giving the fluorenide anion and t-butyl alcohol. (a) Which way does the equilibrium lie, and by how much? b) What is the proportion of the fluorenide anion to fluorene? (c) Why is fluorene so highly acidic, considering the pKa of an average alkane is above 50?arrow_forward
- Show how the following ketones might be synthesized from the indicated acids, usingany necessary reagents.(b) methyl cyclohexyl ketone from cyclohexanecarboxylic acidarrow_forwardDraw the structure of the hydroxyaldehyde product from the self-aldol reaction of each of the following aldehydes: (a) propanal; (b) phenylethanal; (c) 3-phenylpropanal; (d) benzaldehyde.arrow_forwardPlease explain the synthesis. Identify SN1, SN2, E1, E2, nucleophiles and ekectrophiles.arrow_forward
- Propanal and propanone react in a similar way with acidified aqueous potassium cyanide, KCN. For this reaction to occur reasonably quickly, the pH of the solution should be approximately 4. The reaction of propanal proceeds with acidified potassium cyanide proceeds more rapidly than that of propanone. Referring to the mechanism of the reactions, explain this phenomenon.arrow_forward(a) Propose a mechanism for the conversion of cis-hex-3-ene to the epoxide (3,4-epoxyhexane)and the ring-opening reaction to give the glycol, hexane-3,4-diol. In your mechanism, payparticular attention to the stereochemistry of the intermediates and products.(b) Repeat part (a) for trans-hex-3-ene. Compare the products obtained from cis- andtrans-hex-3-ene. Is this reaction sequence stereospecific?arrow_forwardIndicate the reagents and conditions to carry out the following transformations.arrow_forward
- A common illicit synthesis of methamphetamine involves an interesting variation of the Birch reduction. A solution of ephedrine in alcohol is added to liquid ammonia, followed by several pieces of lithium metal. The Birch reduction usually reduces the aromatic ring, but in this case it eliminates the hydroxy group of ephedrine to give methamphetamine. Propose a mechanism, similar to that for the Birch reduction, to explain this unusual course of the reaction.arrow_forwardWhen phenyl 3,4-dimethylbenzoate undergoes electrophilic aromatic substitution, one ring reacts much more readily than the other. (a) Which one is it? Encircle the ring (b) Explain your answer. (c) Draw the resulting product/s when it undergoes bromination reaction. Product (c) (a) Explanation (b)arrow_forwardDraw the chemical structure of a 1,2,3-triazole and showv how it can be synthesized from (b) basic starting materials. Comment on the acidity and basicity of triazoles. Comment on their reactivity towards electrophilic aromatic substitution relative to pyridines and pyrroles.arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning