Concept explainers
(a)
Interpretation:
The major product of the given reaction is to be stated.
Concept introduction:
The reaction of an ester with excess Grignard reagent followed by hydrolysis converts an ester into tertiary alcohol through tetrahedral intermediate. The Grignard reaction takes place in three steps. The first step is addition of Grignard reagent. The second is elimination of alkoxide followed by formation of
(b)
Interpretation:
The synthesis of
Concept introduction:
The reaction of an ester with excess Grignard reagent followed by hydrolysis converts an ester into tertiary alcohol through tetrahedral intermediate. The Grignard reaction takes place in three steps. The first step is addition of Grignard reagent. The second is elimination of alkoxide followed by formation of ketone. The third step is addition of another Grignard reagent followed by formation of an alkoxide. The fourth step is hydrolysis of an alkoxide to yield tertiary alcohols.
(c)
Interpretation:
The preparation of Lexan with the use of diethyl carbonate instead of phosgene and the preparation of Sevin (an insecticide) with the use of diethyl carbonate instead of methyl isocyanate are to be stated.
Concept introduction:
Diethyl carbonate is an ester (carbonic acid and ethanol). It is a liquid reagent that is easy to handle. However, phosgene is a corrosive and highly toxic. Diethyl carbonate successfully replaces phosgene in the synthesis of Lexan and Sevin.
Want to see the full answer?
Check out a sample textbook solutionChapter 21 Solutions
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
- From which starting materials can the product formed as a result of the following reaction be synthesized? A. Acetophenone and butanal B. Benzaldehyde and 3-pentanone C. Benzaldehyde and 2-pentanone D. Acetophenone and 2-butanonearrow_forwardWhat will be the major product if 1-hexanol is oxidized with pyridinium chlorochromate in dichloromethane as the solvent? Select one: A. hexanone B. hexanoic acid C. hexanal D. propyl propanoate What is the minor product obtained when (Z)-1-bromo-2-methylbut-1-ene reacts with HBr? Select one: A. 1,2-dibromo-2-methylbutane B. 2,2-dibromo-1-methylbutane C. 1,2-dibromo-1-methylbutane D. 1,1-dibromo-2-methylbutanearrow_forwardEvaluate the chemical reactions carefully. Predict the reagents required (marked with letters) in order to satisfy the given reactions. A.) Synthesis of 4-octanol Aarrow_forward
- i. Define Hemiacetal, Acetal and Ketal. ii. Give the structure of the product formed from the reaction of propanal with 1M ethanol in dry acid. iii. What happens when Further 1M of ethanol is added to above?arrow_forwardWhich of the following reactions will result in the formation of an acyl halide? Select one: a. The reaction of a carboxylic acid with phosphorus trichloride. b. The treatment of an alcohol with ethyl bromide. c. The reaction of an ester with hydrochloric acid. d. The addition of an alkene to dilute hydrochloric acid.arrow_forward11. Starting with 1,3-propanediol, ethanol, and 1-propanol, design a synthesis for 2-ethylpentanoic acid. Use any other reagents that are needed.arrow_forward
- 1. Nitrile hydrolysis to prepare carboxylic acids. a. What gas is given off in this reaction? How can it be detected chemically? b. Which spectroscopic method could be used to follow this reaction? What would you expect to see? How would you know when the reaction is complete?arrow_forwardWhich of the following products could you not create using malonic acid ethyl ester as a starting material? A. diethyl-2,2-dialkylmalonate B. maleic acid C. Carboxylic acid D. 2,2-dialkylmalonic acid E. diethyl 2-alkyl malonatearrow_forwardA. In the synthesis of 1-bromobutane, what is the inorganic by-product left in the reaction flask following the distillation? Why was the bromoalkane the bottom layer in the separatory funnel? B. Predict the product when 1-methylcyclohexanol reacts with H2SO4 and KBr. Show the mechanism.arrow_forward
- 2. Which of the following alkynes will form only 1 product in acid-catalyzed hydration? a. 2-pentyne b. 3-hexyne c. 3-pentyne d. 1-hexyne 3. Which of the following statements best describes the general reactivity of alkynes? a. An alkyne reacts as an electrophile and is, therefore, electron poor. b. Alkynes undergo electrophilic addition reactions just like alkenes. c. An alkyne reacts as an electrophile and is therefore electron-rich. d. An alkyne reacts as a nucleophile and is therefore electron-poor.arrow_forward37. Which of the following compounds gives a primary alcohol upon reaction with phenylmagnesium bromide? Assume the usual acid work-up. A. 2-Methyl oxirane B. Ethylene oxide C. Ethyl formate D. Carbon dioxide 38. Which of the following compounds is the strongest base? A. (CH3);CuLi B. CH3LI C. CH3ZNB. D. CH3MBB. 39. In the following compound which is the most basic nitrogen? HN A CH2CH2NH2 40. Choose the reaction sequence that will best carry out the following transformation: HO CH2CH3 C. C. H3C CH3 CH3 CH3 0 1 + + CH3ONA + CH;CH2Br i) H20, H A. R) 1 + CH3CH2ONA В. ii) H2O, H i) H20, H* c) CH;CH2Br + Mg, ELO C. i) add 1 il) H2O, H* 0 1+ CH3CH20OH + Mg H) H20, H'arrow_forward9. Give the product structure and the mechanism for the reaction of diethyl carbonate with ethyl 3-phenylpropionate reacted sequentially with a. sodium ethoxide in ethanol. b. sodium hydroxide. c. aqueous acid. d. heat.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