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- 3A Complete the reactions below. H₂SO4/H₂O HgSO4 A NaBH4 EtOH B лH₂SO4 C1. Propose reasonable mechanisms for the following transformations: OH H+ 女 ΗH₂C ཏཱཏི 1 ནི OH 1. Br2, PBг3 2. H₂O H3C OH Br The a-bromination of carbonyl compounds by Br2 in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br2 reacts in an a-substitution reaction. Hydrolysis of the acid bromide completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions :0: H3C Br Br + :::OH2 Br H₂O H3C Br за
- 2. Provide a mechanism for the following transformation: OH O ملی OH H3O Δ لا + CO21. Give systematic names for the following substituted benzene derivatives. a) b) b) CI NH₂ 2. Give the type of effects the following substituents have on the benzene ring. Do they activate or deactivate the benzene ring? a) NH₂ OH OHNonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.
- Terpin, prepared commercially by the acid-catalyzed hydration of limonene, is used medicinally as an expectorant for coughs. (a) Propose a structural formula for terpin and a mechanism for its formation. (b) How many cis, trans isomers are possible for the structural formula you propose?Provide reagents/conditions to accomplish the following syntheses. Several steps are required in some cases. H2N NH2 Но TH. NH2 HOWhich set of starting materials could be used to prepare the following compound in one step? * Meo -CHO Meo сно CO,Me MeO Meo .CO,Me Meo Meo CO,Me CO,Me Meo. CO,Me Meo CO,Me RCO,H Meo `cO,Me Meo CO,Me
- Indicate the products A and B that are obtained in the following reactions: OH CH3 + HOCH2-CH₂OH + TSOH → A 1° NaH/THF A + →> B 2º C6H5-CH2Cl Briefly comment on each reaction.1. Predict the product and provide the mechanism for the following reversible nucleophilic addition. NaOH in H₂O 2. Predict the product and provide the mechanism for the following reversible nucleophilic addition. H2SO4 (cat) H EtOHWhich of the following structures and IUPAC names are incorrectly matched? * oe (A) Methyleyclohexanoate (В) `NH2 Br 4-Bromo-3-chlorohexanamide 2-Ethoxypentane (D) HOOC HOOC 3,5-Nonanedioic acid В A D