(a) (b) Briefly explain why the alpha hydrogens of carbonyl compounds are much more acidic than typical C-H bonds, such as those in methane. Predict the structure of the product formed in the following reaction. Explain your reasoning. or PPh3 O
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- (b) State the reagents needed to convert benzoic acid into the following compounds. (i) C6H§COCI (ii) C,H$CH2OH (iii) C6H$CONHCH3A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons.(a) Draw the resonance forms of a carboxylic acid that is protonated on the hydroxyoxygen atom.(b) Compare the resonance forms with those given previously for an acid protonated on thecarbonyl oxygen atom(a) Explain how NaBH, in CH;OH can reduce hemiacetal A to 1,4-butanediol (HOCH,CH,CH,CH,OH). (b) What product is formed when A is treated with Ph;P=CHCH,CH(CH),? (c) The drug isotretinoin is formed by reaction of X and Y. What is the structure of isotretinoin? Although isotretinoin (trade name Accutane or Roaccutane) is used for the treatment of severe acne, it is dispensed under strict controls because it also causes birth defects. PPha NaOCH,CH3 HO- isotretinoin HO A Br X Y
- Amphetamine is a powerful stimulant of the central nervous system.Draw the products formed (and show the flow of electrons) from the acid-base reaction of amphetamine with (a) HCl and with (b) NaH.Give reasons for the following :(i) Phenol is more acidic than methanol.(ii) The C—O—H bond angle in alcohols is slightly less than the tetrahedral angle (190°28′).(iii) (CH3)3C—O—CH3 on reaction with HI gives (CH3)3C—I and CH3—OH as the main products and not (CH3)3C—OH and CH3—I.A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons. (b) Compare the resonance forms with those given previously for an acid protonated on thecarbonyl oxygen atom.(c) Explain why the carbonyl oxygen atom of a carboxylic acid is more basic than thehydroxy oxygen.
- The hydrocarbon fluorene was treated with potassium t-butoxide in an acid-base reaction, giving the fluorenide anion and t-butyl alcohol. (a) Which way does the equilibrium lie, and by how much? b) What is the proportion of the fluorenide anion to fluorene? (c) Why is fluorene so highly acidic, considering the pKa of an average alkane is above 50?From 1 being the least acidic and 4 being the most acidic, arrange the following organic compounds in terms of increasing acidityDescribe the trends in the acidityand physical properties of carboxylicacids, and explain how their acidityvaries with their substituents.
- (c) Arrange the following compounds in order of increasing acidity, and explain the reasons for your choice of order: phenol, cyclohexanol, 2-fluorocyclohexanol, 2-fluorophenol.(c) Arrange the following compounds in order of increasing acidity, and explain the reasons fo your choice of order: phenol, cyclohexanol, 2-fluorocyclohexanol, 2-fluoronhenolArrange the following molecules in increasing order of acidity. Base it only on their structural differences and explain how it is so. 1. HF, CH3CH2CH2OH, CH3CH2COOH 2. Ethyl amine, Ethanol, Propane