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 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.
(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
- What compounds are formed from the reaction of benzoyl chloride with the following reagents? a. sodium acetate b. water c. excess dimethylamine d. aqueous HCl e. aqueous NaOH f. cyclohexanol g. excess benzylamine h. 4-chlorophenol i. isopropyl alcohol j. excess aniline k. potassium formatearrow_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_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
- Which 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_forwardWhat will be the right combination of reagents to be required for the synthesis of the following compound? a. Ethanal + n-Propylamine b. Ethanal + isopropylamine c. Propanal + Ethylamine d. Ethylamine + Ethanal .arrow_forwardPlease explain the chosen letter. Benzoic acid reacts with conc. HNO3 and conc.H2SO, to give a. o-nitrobenzoic acid b. p-nitrobenzoic acid c. m-nitrobenzoic acid d. p-dinitrobenzoic acidarrow_forward
- 37. 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_forwardHh.10.arrow_forwardCreate 3-methyl-1-butanamine using the four different methods below. a. Gabriel synthesis b. Using sodium azide c. Using a carboxylic acid d. Using an alkyl bromidearrow_forward
- Draw the structure of each alkene expected from the following dehydrations. Label the major product in each case and indicate the mechanisms by which each is produced. + phosphoric acid + sulfuric acid a. cyclohexylmethanol b. 2-methylcyclohexanolarrow_forwardNameand Draw the structures of all possible chemical (Electrophilic aromatic substitution) reactions of the o-propylbenzaldehyde a. Halogenation (Chlorination or Bromination) b. Nitration c. Sulphonation d. Friedel Craft Alkylation e. Friedel Craft Acylationarrow_forwardWhich could explain the stronger acidity of phenols compared to alcohols. Why? a.pi-electron delocalization b.steric effect c.hydrogen bonding d.hyperconjugationarrow_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