a) 2-Hydroxy-2-methylpentanal
Interpretation:
Whether 2-hydroxy-2-methylpentanal is an aldol condensation product or not is to be stated. The aldehyde or ketone precursor from which it can be prepared also is to be stated.
Concept introduction:
To state:
Whether 2-hydroxy-2-methylpentanal is an aldol condensation product or not. Further to state the aldehyde or ketone precursor from which it can be prepared.
b) 5-Ethyl-4-methyl-4-hepten-3-one
Interpretation:
Whether 5-ethyl-4-methyl4-heptene-3-one is an aldol condensation product or not is to be stated. The aldehyde or ketone precursor from which it can be prepared also is to be stated.
Concept introduction:
Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon of the second molecule. The product obtained is a β-hydroxyaldehyde or ketone.
To state:
Whether 5-Ethyl-4-methyl-4-heptene-3-one is an aldol condensation product or not. Further to state the aldehyde or ketone precursor from which it can be prepared.
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Chapter 23 Solutions
Bundle: Organic Chemistry, Loose-leaf Version, 9th + LMS Integrated for OWLv2, 4 terms (24 months) Printed Access Card
- Acid-catalyzed hydrolysis of the following epoxide gives a trans diol. Of the two possible trans diols, only one is formed. How do you account for this stereoselectivity?arrow_forwardWhat is meant by the following terms? Give an example of the reaction in each case.(i) Aldol (ii) Semicarbazonearrow_forwardAldol condensation Indicate the products: CH3-CO-CH3 + CH3-CH2-CHO + NaOH Homo-aldol and hetero-aldo condensation. Are the two produced equally or does one predominate?arrow_forward
- Which of the following is a substrate product when benzene is first treated with Cl2 and FeCl3, and THEN treated (in a second step) with HNO3 and H2SO4?arrow_forwardWhat is the product resulted due to the reaction of 2-hydroxy-3-methoxybenzaldehyde with ethyl bromoacetate in a basic solution indicating all the reagents and intermediates occurred during the reaction? What is the product obtained when product A reacted with ethyl acetate in the same basic solution?arrow_forwardWhich of the following does not support a nucleophilic attack of a covalent catalysis? a. Hydroxyl b. Sulfhydryl c. Imidazole d. Amino e. Methylarrow_forward
- Following is a retrosynthesis for the coronary vasodilator ganglefene. (a) Propose a synthesis for ganglefene from 4-hydroxybenzoic acid and 3-methyl-3-buten-2-one. (b) Is ganglefene chiral? If so, which of the possible stereoisomers are formed in this synthesis?arrow_forward-Hydroxyketones and -hydroxyaldehydes are also oxidized by treatment with periodic acid. It is not the -hydroxyketone or aldehyde, however, that undergoes reaction with periodic acid, but the hydrate formed by addition of water to the carbonyl group of the -hydroxyketone or aldehyde. Write a mechanism for the oxidation of this -hydroxyaldehyde by HIO4.arrow_forwardThe base-promoted rearrangement of an a-haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. Jo Han Sow La NaOH, THF O Nat H3O+ OH NaOH, THF The mechanism involves the following 5 steps: -ō cyclopropanone intermediate 1. Abstraction of a proton to form enolate anion 1; 2. Formation of a cyclopropanone intermediate 2 with expulsion of chloride ion; 3. Addition of hydroxide ion to form tetrahedral intermediate 3; 4. Collapse of the tetrahedral intermediate and breakage of the three-membered ring to form carbanion intermediate 4; 5. Proton transfer to form the rearranged carboxylic acid. For the following reaction, draw the reaction out on paper, and then draw the structure of cyclopropanone intermediate 2 in the window. 1. NaOH, THF 2. H3O* OHarrow_forward
- Which of the following is a substrate product when benzene is first treated with HNO3 and H2SO4, and THEN treated (in a second step) with Br2 and FeCl3 (or FeBr3)? 1-bromo-3-nitrobenzene 1-chloro-1-nitrobenzene 1-bromo-1-nitrobenzene aniline cis-1-bromo-2-nitrocyclohexanearrow_forwardGive all the monobromination products of 2-methylpropane (or isobutane) in presence of heat or energy. Identify the major product and propose a mechanism leading to the formation of the major product. Provide a reaction in the termination step.arrow_forwardWhat are the products obtained (2 stereoisomers A and B) when (Z)-hex-3-ene is treated with Br2 in anhydrous medium? Show the mechanism of this reaction. When the dibromide formed is treated with KOH in EtOH, only (Z)-3-bromohex-3-ene. Explain this result and justify why the E isomer cannot be obtained here. here.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning