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Concept explainers
Interpretation:
Synthetic intermediates A and B have to be drawn.
Concept Introduction:
Conversion of alcohol into
Conversion of primary and secondary alcohols to Chloroalkane is thionyl chloride. The reaction is carried out in the presence of base such as pyridine or trimethylamine.
The reaction of an alcohol with thionyl chloride is the formation of an alkyl Chlorosulfite that converts hydroxide ion (poor leaving group) into Chlorosulfite (good leaving group). Nucleophilic displacement of this leaving group gives product.
Leaving group: Leaving group can be any groups or atoms that get detached from either neutral or charged organic compounds. The stability of the leaving group is to stabilize the electron density that results from heterolysis cleavage of bond.
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Chapter 10 Solutions
Organic Chemistry
- In 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_forwardThe formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol intermediate and molecular bromine. The intermediate then undergoes acid-catalyzed tautomerism to form succinimide, the byproduct of the reaction. Propose a curved-arrow mechanism for the conversion of NBS into succinimide that also accounts for the formation of Br2.arrow_forwardFats can be either optically active or optically inactive, depending on their structure. Draw the structure of an optically active fat that yields 2 equivalents of stearic acid and 1 equivalent of oleic acid on hydrolysis. Draw the structure of an optically inactive fat that yields the same products.arrow_forward
- Identify compounds A, B, and C. a.) Compound A has molecular formula C8H12 and reacts with two equivalents of H2. A gives HCOCH2CH2CHO as the only product ofoxidative cleavage with O3 followed by CH3SCH3. b.) Compound B has molecular formula C6H10 and gives(CH3)2CHCH2CH2CH3 when treated with excess H2 in the presence ofPd. B reacts with NaNH2 and CH3I to form compound C (molecularformula C7H12).arrow_forward5. Butylated hydroxy toluene (BHT) is an anti-oxidant added to many food products (e.g. breakfast cereals) to increase their shelf-life. BHT is synthesized from p-cresol by reaction with 2-methylpropene in the presence of phosphoric acid. a) What is the structure of BHT ? b) Account for the regioselectivity of tert-butyl group substitution in the synthesis of BHT. c) Propose a mechanism to explain the formation of the electrophile in the synthesis of BHT.arrow_forwardAn acid–base reaction of (R)-sec-butylamine with a racemic mixture of 2-phenylpropanoic acid forms two products having different melting pointsand somewhat different solubilities. Draw the structure of these twoproducts. Assign R and S to any stereogenic centers in the products.How are the two products related? Choose from enantiomers,diastereomers, constitutional isomers, or not isomers of each other.arrow_forward
- Identify compounds A, B, and C. a. Compound A has molecular formula C8H12 and reacts with two equivalents of H2. A gives HCOCH2CH2CHO as the only product of oxidative cleavage with O3 followed by CH3SCH3. b. Compound B has molecular formula C6H10 and gives (CH3)2CHCH2CH2CHCH3 when treated with excess H2 in the presence of Pd. B reacts with NaNH2 and CH3I to form compound C (molecular formula C7H12).arrow_forwardIsopulegol is formed as a single stereoisomer. Account for the fact that only a single stereoisomer is formedarrow_forwardSharpless epoxidation of allylic alcohol X forms compound Y. Treatment of Y with NaOH and C6H5SH in an alcohol–water mixture forms Z. Identify the structure of Y and draw a mechanism for the conversion of Y to Z . Account for the stereochemistry of the stereogenic centers in Z. Z has been used as an intermediate in the synthesis of chiral carbohydrates.arrow_forward
- (a) Draw a stepwise mechanism for the reaction of ethyl hexa-2,4-dienoate with diethyl oxalate in the presence of base. (b) How does your mechanism explain why a new carbon–carbon bond forms on C6? (c) Why is this reaction an example of a crossed Claisen reaction?arrow_forwardThe chiral hydroxyl compound P, C7H14O contains a five-membered ring and showspositive result in iodoform test. Compound P and sodium bromide can be produced byrefluxing compound Q with aqueous NaOH solution. Compound P is heated withbenzoic acid in the presence of concentrated H2SO4 to form a sweet-smelling product,compound R. Deduce the structure of P, Q and R. PLEASE PROVIDE CLEAR HAND WRITING AND SOLUTIONSarrow_forwardDraw the structure of sodium tetradecyl sulfate and ciprofloxacin and state how the activity of the drug is influenced by alkane groupings.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
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