Concept explainers
(a)
Interpretation: Two different halo
Concept introduction: Alkylation of
Lithium diisopropylamide (LDA) is a sterically hindered strong base. In an unsymmetrical ketone, it abstracts hydrogen from least substituted carbon to form kinetic product.
(b)
Interpretation: The synthesis of compound A from acetoacetic ester is to be devised.
Concept introduction: Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively.
Trending nowThis is a popular solution!
Chapter 23 Solutions
Organic Chemistry
- Identify the acetal carbons in A, and draw the products formed by hydrolysis of A with aqueous acid.arrow_forward5) Draw the enols available to compounds A-D. Explain why A is 100% enolized but B, C, and D are 100% ketone. B Darrow_forward4) Give an example of an enol which would tautomerize into a) an aldehyde and b) a ketone.arrow_forward
- 1,2-Diols are converted to carbonyl compounds when treated with strong acids, in a reaction called the pinacol rearrangement. (a) Draw a stepwise mechanism for this reaction. (Hint: The reaction proceeds by way of carbocation intermediates.) (b) Assuming that the pinacol rearrangement occurs via the more stable carbocation, draw the rearrangement product formed from diol D.arrow_forwardDraw the organic products formed when attached allylic alcohol A is treated with following reagent. [1] PBr3; [2] LiAlH4; [3] H2Oarrow_forwardBased on the following groups Acid chloride, Amide, Ester a) Select the most reactive group towards nucleophilic acyl substitution reaction. b) Describe the reasons in question (a). c) Identify the group(s) that can been synthesized from acid chloride.arrow_forward
- Draw the products formed when p-methylaniline (p-CH3C6H4NH2) istreated with following reagent. CH3COCl, AlCl3arrow_forwardQuinapril (trade name Accupril) is used to treat high blood pressure and congestive heart failure. One step in the synthesis of quinapril involves reaction of the racemic alkyl bromide A with a single enantiomer of the amino ester B. (a) What two products are formed in this reaction? (b) Given the structure of quinapril, which one of these two products is needed tosynthesize the drug?arrow_forwardExplain the mechanism of acid catalysed hydration of an alkene to form corresponding alcohol.arrow_forward
- 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
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning