QI/ Arrange and give reason the following sets of compounds in order of: 1) Increasing acidity CH Ph CHCH, (a) (b) (c) (d) 2) Give more yield in cross Aldol condensation p-methyl benzaldehyde , p-methoxy benzaldehyde , benzaldehyde , p-nitro benzaldehyde 3) Stability of carbanion ion CH3 CN . CH3 C-OCH3 CH3-C-CH, . CH,NO2
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- Why do you suppose ketone halogenations in acidic media are referred to as being acid-catalyzed, whereas halogenations in basic media are base-promoted? In other words, why is a full equivalent of base required for halogenation?What compound is the major product of the reaction sequence shown below? (1) KCN ethanol Он (A) NH2 (B) (2) LIAIH, (xS)/ether (3) dil. H* H;O он NH2 OH (C) (D) Compound C Compound D )Compound A O Compound BQ1/A) Arrange the following sets of compounds in order of: 1) Increasing acidity H₂C CH₂ H₂C OCH₂CH₂ OCH₂CH3 Ph, изза паззакон показзаки здають 2) Increasing yield in cross Aldol condensation p-methyl benzaldehyde, p-methoxy benzaldehyde, benzaldehyde, p-nitro benzaldehyde 3) Stability of carbanion ion O 11 유 CH3-CN, CH3-C-OCH3. CH3-C-CH3, CH3NOz
- Nucleophilic addition to ketone - Match the reagent with the reaction. (each used once) OH H3CO OCH3 OH HO. OH (A) (B) PPh3=CHCH3 1) CH3MgBr 2) H3O+ (C) CH3-OH (D) NaBH4 (E) 1) NaCN (aq) 2) H3O+ (F) H₂O OH CO₂HA good Williamson synthesis of ethyl methyl ether would beCH3CH2¬O- Na+ + CH3I ¡ CH3CH2¬O¬CH3 + NaIsodium ethoxide methyl iodide ethyl methyl etherWhat is wrong with the following proposed synthesis of ethyl methyl ether? First, ethanolis treated with acid to protonate the hydroxy group (making it a good leaving group), andthen sodium methoxide is added to displace water.CH3CH2(incorrect synthesis of ethyl methyl ether)OH + H+ CH3CH2 OH2+CH3CH2 O CH3(c) With reference to the following reaction scheme: Met N Me Boc 20 OMe DIBAL, toluene, -78 °C then H₂O w/up Me+N Mé Boc 21 H Useful structure: DIBAL= H₂ Al Y Bary (i) Provide a curved arrow mechanism for the reduction of ester 20 to aldehyde 21. (ii) Explain why the reduction of ester 20 selectively affords aldehyde 21 in the presence of DIBAL, whereas treatment of 20 with LiAlH4 leads to over-reduction.
- Complete the following reactions by giving appropriate reagents: Zn(Hg) (1)? AICI HCI HNO₂ CI H₂SO4 (3)? (4)? NO₂ (2)?If anhydrides react like acid chlorides with the nucleophiles, draw the products formed when each of the following nucleophiles reacts with benzoic anhydride [(C6H5CO)2O]: (a) CH3MgBr (2 equiv), then H2O; (b) LiAlH4, then H2O; (c) LiAlH[OC(CH3)3]3, then H2O.Nonanal is an aldehyde used extensively in the perfume industry due to its rose-like smell. It can be synthesized from 1-nonene. What reagents are needed to accomplish this multistep synthetic transformation? ? 1) H₂SO4; 2) NaOCI/CH3CO₂H/0° C 1) a) BH3/THF, b) HO-, H₂O2, H₂O; 2) PCC/CH₂Cl2 1) a) BH3/THF, b) HO-, H₂O2, H₂O; 2) H₂CRO4 1) H₂SO4; 2) H₂CrO4 1) H₂SO4; 2) PCC/CH2Cl2
- (iii) Provide detailed reaction mechanisms for the intermolecular aldol reaction of D and subsequent dehydration to give E. D E (iv) Draw the structure of lithium diisopropylamide (LDA) and the structure of the product G, which will form from F under the following reaction conditions. F NaOH OEt i) LDA, -78 °C, THF ii) Mel, -78 °C to 0°C GWhat compounds will be a major product of the reaction sequence below (1) Brz, hv (2) Mg/ether он OH (A) (B) (3) (4) dil. H* /H2O OH (C) (D) он Compound C Compound D Compounds A and B Compounds B and D (6)Which of the following is a major product of the reaction shown? (CH3),CHCH;NH2 **** HN- H* (cat./H;0 (A) (B) N- (C) (D) Compound D OCompound C O Compound A Compound B