Concept explainers
Interpretation:
The correct enantiomer of
Concept introduction:
The alcohols on reaction with
As the hydroxyl group of alcohol acts as a nucleophile, there is no change in configuration of alcohol and tosylate (
The thiol can be prepared from
The
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Organic Chemistry - Standalone book
- Account for the fact that treating propenoic acid (acrylic acid) with HCl gives only 3-chloropropanoic acid.arrow_forwardIn the chemical synthesis of DNA and RNA, hydroxyl groups are normally converted to triphenylmethyl (trityl) ethers to protect the hydroxyl group from reaction with other reagents. Triphenylmethyl ethers are stable to aqueous base but are rapidly cleaved in aqueous acid. (a) Why are triphenylmethyl ethers so readily hydrolyzed by aqueous acid? (b) How might the structure of the triphenylmethyl group be modified to increase or decrease its acid sensitivity?arrow_forwardDibenzalpropanone is a compound that can absorb UV rays and can be used as a sunscreen. Write down the reagents used to synthesize the compound dibenzalpropanone.arrow_forward
- Reaction of 1-butanol with periodane gives Butanal Propanoic acid 2-Butanone Butanoic acid as the major product.arrow_forwardPredict the products formed when cyclohexanone reacts with the following reagents.(a) CH3NH2, Harrow_forwardWhich one of the following combinations give ethoxy benzene? A Sodium ethoxide and chlorobenzene Ethyl bromide and sodium phenoxide Ethanol and benzene Ethyl chloride and phenolarrow_forward
- Compound A and compound B both have molecular formula C6H12. Both compounds produce epoxides when treated with a peroxy acid (RCO3H). The epoxide resulting from compound A was treated with aqueous acid (H3O+) and the resulting diol has no chiral centers. Identify the two possible structures for compound A (enter two numbers separated by commas with no spaces, e.g. "1,2") The epoxide resulting from compound B was treated with (H3O*) and the resulting diol was a meso compound. Identify compound B 2 3 potn 7 1 5 6 4 8arrow_forwardPredict the products formed when cyclohexanecarbaldehyde reacts with the following reagents.(a) PhMgBr, then H3O+ (b) Tollens reagent (c) semicarbazide and weak acid(d) excess ethanol and acid (e) propane-1,3-diol, H+ (f) zinc amalgam and dilute hydrochloric acidarrow_forwardThe following molecule belongs to a class of compounds called enediols; each carbon of the double bond carries an-OH group. Draw structural formulas for the a-hydroxyketone and the a-hydroxyaldehyde with which this enediol is in equilibrium. CH-OH a-Hydroxyaldehyde = C-OH= a -Hydroxyketone ČH3 An enediolarrow_forward
- What reactions and reagents can be used to make phenol from benzene if electrophilic aromatic substitution reactions are excluded and benzene is the only source of carbon?arrow_forwardThe ketone 2-heptanone has been identified as contributing to the odor of a number of dairy products, including condensed milk and cheddar cheese. Describe the synthesis of 2-heptanone from acetylene and any necessary organic and inorganic reagents.arrow_forwardEthyl butyrate, CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring.It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l). The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0% yield. How many grams would be produced from 8.50 gof butanoic acid and excess ethanol? Express your answer in grams to three significant figures.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning