Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict themajor products of the reactions of naphthalene with the following reagents.(a) HNO3, H2SO4
PQ-18. Which set of reagents will yield this ether at the fastest rate?
(A)
(C)
OH
ONa
EtONa
EtOH
(B)
(D)
ONa
EtONa
EtCl
Devise a stepwise mechanism for the following reaction. The reaction does not take place by direct electrophilic aromatic substitution at C2.
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- Which compounds give an SN2 substitution reaction on treatment with alcoholic NaSH? (b) Which compounds give an E2 elimination reaction on treatment with alcoholic KOH? (c) Which compounds do not react under either of the previous reaction conditions?arrow_forwardAziridines are heterocycles that contain an N atom in a three-membered ring. Like epoxides, aziridines are strained and reactive because the 60° bond angles of the three-membered ring deviate greatly from the theoretical tetrahedral bond angle. One step in the synthesis of the drug oseltamivir (trade name Tamiu, Section 3.2) involves the conversion of amine X to diamine Y, a reaction that occurs by way of an intermediate aziridine. Draw a stepwise mechanism for the conversion of X to Y. Indicate the structure of the aziridine intermediate, and explain the trans stereochemistry of the two amines in Y.arrow_forwardIdentify the lettered compounds in each reaction sequence.Draw the product formed when phenylacetonitrile (C6H5CH2CN) istreated with below reagent. H2O, −OHarrow_forward
- Draw the major organic product of the following reaction sequence. 1) Hg(OAc)2, MeOH 2) NaBH4 ?arrow_forwardAziridines are heterocycles that contain an N atom in a three-membered ring. Like epoxides, aziridines are strained and reactive because the 60° bond angles of the three-membered ring deviate greatly from the theoretical tetrahedral bond angle. One step in the synthesis of the drug oseltamivir (trade name Tamiflu, Section 3.2) involves the conversion of amine X to diamine Y, a reaction that occurs by way of an intermediate aziridine. Draw a stepwise mechanism for the conversion of X to Y. Indicate the structure of the aziridine intermediate, and explain the trans stereochemistry of the two amines in Y.arrow_forwardConsider carbonyl compounds A– E attached below. Rank A–E in order of increasing amount of hydrate formed when treated with aqueous acid.arrow_forward
- Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict themajor products of the reactions of naphthalene with the following reagents.(a) HNO3, H2SO4 (b) Br2, FeBr3arrow_forward2) a) Complete the following scheme with needed reagents and Product A and Product B: OH Хон NaH Product A MS has an M* (100%) and M+2 (97%) or 1:1 Product B Product Carrow_forwardDevise concise syntheses for the following transformations. Clearly show the reagent andproduct for each step. All syntheses can be accomplished in two steps.arrow_forward
- A key step in a synthesis of the antimalarial drug quinine involves an intramolecular nucleophilic substitution that converts A to B. Draw the structure of B and give the reagents needed to convert B to quinine.arrow_forwardWhen (R)-6-bromo-2,6-dimethylnonane is dissolved in CH3OH, nucleophilic substitution yields an optically inactive solution. When the isomeric halide (R)-2-bromo-2,5-dimethylnonane is dissolved in CH3OH under the same conditions, nucleophilic substitution forms an optically active solution. Draw the products formed in each reaction, and explain why the difference in optical activity is observed.arrow_forwardWhat steps are needed to convert benzene into p-isobutylacetophenone, a synthetic intermediate used in the synthesis of the anti-inammatory agent ibuprofen.arrow_forward
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