OH - NH, Br2/KOH →product; 1. (a-hydroxy amide) Product of this Hoffmann bromamide reaction is : OH (a) Ph – Ĉ-CH3 (Ъ) Ph — CHO (c) Ph- CH3 (d) Ph – CH2 -NH2 NO2
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- (b) State the reagents needed to convert benzoic acid into the following compounds. (i) C6H§COCI (ii) C,H$CH2OH (iii) C6H$CONHCH351. Which is NOT a valid resonance structure for the conjugate base of this molecule? (A) (C) S (A) OEt O :O: : OEt HBr ROOR OCH 3 (B) 52. What is the major product of this reaction sequence? O PPh3 (D) 11 Mg ether (B) de OEt :0 aom Сосно LOCH 3 53. Which reagent is necessary for this transformation? (D) H OEt H OEt CH31 PPh3 ACS 56.(a) (b) HO N N-H Catalytic H+ (-H₂O) ? (c) NH2 HO N (d)
- Determine whether each of the following syntheses requires a reaction that alters the carbon skeleton. (a) (b) OH (c) (d) OCH,CH3 CH3 (e) OH (f) H,CO он H;CO. (g) H3CO, (h) H3CO. NO2 NO2Determine product (A) of the reaction (1) NK + DMF CH2 – Br (A) (81%) (2) HO¯/H2O (Benzyl bromide) (a) Ph – NH2 (c) Ph – CH2 – NH – CO,H (b) Ph – CH2 – NH2 (d) Ph – CH, - NH – CHO(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
- Which ester can be easily condensed with NaOEt to produce B-keto ester salt? (A) Ph-C–OEt (B) СH, CH, ҫ OEt (C) CH;-CH-Ç-OEt (D) CH, 0 Ҫ Н CH; Ö6. Which of the following will not give Hoffmann bromamide reaction ? (а) CH3 - С-NH2 (Ъ) Ph — С-NH, || (с) CН3 - С-NH - Br (d) Ph – C– NH – Ph1. Give IUPAC names for the following carboxylic acids: (c) CH;CH-CHCH,CH2CH3 (а) (b) Br CH;CHCH,ČOH CH;CHCH2CH,čOH (d) (e) H HO,C Co,H CH2CH,COH
- (c) Reaction of acetanilide with bromine Br: CH3 (d) Hydrolysis of 4-bromo-2-chloroacetanilide with HCl and ethanol HCI CH,CH,OHWhich of the following reactions will synthesize phenol from benzene? 1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) warm H2SO4 and H2O 1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) CuCN; 5) dilute acid and heat 1) Acetyl chloride & AlCl3; 2) bleach 1) Ph-N2+ + KI; 2) BrMgCH=CH2 in ether, followed by H3O+; 3) warm, conc'd KMnO4 1) Cl-CH(CH3)-CH2CH2CH3 + FeBr3; 2) hot, conc'd KMnO4Predict the products of the following acid-base reactions. If the equilibrium would not result in the formation of appreciable amounts of products, you should so indicate. In each case label the stronger acid, the stronger base, the weaker acid, and the weaker base: (a) CH3CH=CH2 + NANH2 (d) CH3C=C: + CH;CH2OH → (e) CH3C=C:- + NH¾CI – | (b) CH;C=CH + NaNH2 (c) CH3CH2CH3 + NANH2 → | HAS