Ch18 - 396(b S olutions XO I.~ C HAPTER 18 C I MeOH...

Info iconThis preview shows pages 1–3. Sign up to view the full content.

View Full Document Right Arrow Icon
397 BOH (c) Cyclobutyl butanoate (D '2-Arninopropanamide ~OH+ HCI CHAPTER 18 Solutions to the Problems Solutions + ~O (e) Diethyl adipate + NaHC0 3 (b),~ . OEt In order to dissolve in water, the phthalimide must be deprotonated to give the negatively-charged phthalimide anion. The question becomes whether sodium bicarbonate is a strong enough base to deprotonate phthalimide according to the following equilibrium: ~NH o pK a = 8.3 £roblem 18.2 Will phthalimide dissolve in aqueous sodium bicarbonate? (d) N-( I-Methylheptyl)succinarnide o . rZ N-?H(CH')5CH, ~ CH 3 o The pK a of phthalimide is 8.3, w"i1e the pK a of carbonic acid H2C03, which dissociates into H20 and CO 2, is 6.4. Because equilibria in acid-base reactions favor formation of the weaker acid (phthalimide), the equilibrium will be to the left and the phthalimide will not dissolve. Problem 18.3 Complete and balance equations for the hydrolysis of each ester in aqueous solution; show each product as it is ionized under the indicated experimental conditions. (al c:::e COOC :'2 NaOH H,O. c:::e coo - No'+ ? CH,O H ~ COOCH 3 . # COO· Na+ £rQble m 18.1 Draw a structural formula for each compound. (a) N_CycJohexylacetamide. (b) I-Methylpropyl met!}anoate Problem 18:4 Complete equations for the hydrolysis of the arnides in Example 18.4 in concentrated aqueous NaOH. Show all products as they exist in aqueous NaOH, and th.,e number of moles of NaOH required for hyd!olysis of each amide. . Each product is shown as it would exist in aqueous NaOH. o 0 II H 0 II (a) CH 3 C-N-CH 3 + NaOH 2 .. CH 3 CO-Na+ + (CH3hN H I . CH 3 , ~hapler 18: FUflctional Derivatives of CarboxyliC Acids OH OH OH 2. HCI .. Fexofenedine hydrochloride (racemic) OH Solutions °XOO CH3 CI. HO I ~ .' # 1, NaBH 4 NaOH,.H 2 9/EtOH , .. pH 7-8,35 hours o MeOH Ornate bunertlyfish Chae/u(/un omat;ss;mus Maui. Hawaii °XO OHC1 HO , I . ~ , # (b) 396 Problem 17.51 So fa.r, you have seen a number of reduci~g agents used in re?ctions. Functional groups react differently with of these ~eagen~s. WIth this III mllld, complete the followlIlg reaction, wh!ch IS the last step in a synthesis offexofenadine a nonsedatlllg antlhlstamme sold under the trade name of Allegra. " ' . Note that fexofenedine is -actually sold as ,the hydrochloride salt to aid solubility.
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
398 Solutions Chapter J8: Functional Derivatives of Carboxylic Acids .,' (b) + NaOH Problem 18.5 Synthesis of nitriles by nucleophilic displacement of halide from an alkyl halide is practical only with primary and secondary alkyl halides. It fails with tertiary alkyl halides. Why? What is the major product of the following reaction? s KCN 0-' .. ~ CH 3 + HCN + KCI O< CH CI ethanol, . water. Cyanide ion is both a base and a nucleophile. With a tertiary halide (a lot of steric hindrance to backside
Background image of page 2
Image of page 3
This is the end of the preview. Sign up to access the rest of the document.

{[ snackBarMessage ]}

Page1 / 22

Ch18 - 396(b S olutions XO I.~ C HAPTER 18 C I MeOH...

This preview shows document pages 1 - 3. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online