6) Give the structures of the compounds A-E in the synthetic sequences below. PBr3, Br2 NH3, excess LOH A B you 1) NaNH2 (1 equiv) H2O, HgSO4 Br2 excess HCECH C D E H2SO4 NaOH excess 2) BuCI (1 equiv)
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- The nucleophilic aromatic substitution reaction shown in the box proceeds via a benzyne intermediate and results in two organic products. What are structures of these products? CH3 NaNH2 CI liquid NH3 A) CH3 CH3 CH3 CH2NH2 B) + CI + -NH2 -NH2 NH2 C) CH3 D) CH3 CH3 CH3 -NH2 -NH2 -NH2 NH2 NH2 A ВWhich synthetic sequence will give the following overall transformation? how? (1) LDA / THF; (2) CH31; (3) H2 / Pd on C a. H2 / Pd on C b. (1) HBr; (2) CH3LI; (3) H2 / Pd on C C. (1) BH3 / THF; (2) H2O2: (3) CH3LI d. (1) Li / NH3liq): (2) CH3I Oe.What reagents are necessary to carry out the conversion shown? OH CH₂CH3 CH₂CH3 O Na₂Cr₂O7/H2SO4/H₂O; CH3CH₂CH₂CH₂MgBr; H₂O O Na2Cr₂O7/H2SO4/H2O; SOCI2; excess CH3CH₂CH₂CuLi; H₂O O Na₂Cr₂O7/H₂SO4; excess CH3CH₂MgBr; H3O+ O Na₂Cr₂O7/H₂SO4/H₂O; SOCI₂; excess CH3CH₂MgBr; H₂O O Na₂Cr₂O7; SOCI2; CH3CH₂MgBr; H₂O
- (i) () ВН3, THF B (ii) H202/HO (ii) Br SH Br2 C D (ii) POCI3 CH-CHз Рyridine HO' E (iv) (i) R2BH (ii) H2O2, HO LLBromide Bhas normal activity (for a secondary bromide) towards SN1 substitution, but A has much higher reactivity and Chas much lower reactivity.3) Please draw the structures that correspond to omitted structure for each of the following synthetic sequences. HO Cro3 Cro3 (a) Product `OH Product H,0 HO PCC Cl РСС (b) Product (e) Product OH HO РСС NABHA (f) Starting Material (c) Product OH ELOH
- Draw the structure of each molecule. (a) (E)-4-carbamoylbut-3-enoic acid; (b) 3-carbamoylpentanediamide; (c) 4,6-dioxohexanenitrile; (d) (1S,2S)-2-methoxycyclopent-3-ene-1-carbonitrile; (e) cyclohexa-3,6-diene-1,3-dicarboxylic acidWhat is an appropriate stepwise synthesis for the conversion shown? a-do O PBr3; PCC; H₂O O PBr3; H₂SO4; PCC; H₂O O KMnO4; CrO3; H₂O O KMnO4/NaOH/H₂O (hot); H₂O O KMnO4/NaOH/H₂O (cold); CrO3/H₂SO4/H₂O -OH OSelect the letters corresponding to the reagents, in the appropriate sequence, to synthesize the compound below from the starting material indicated. Assume that you can separate ortho and para disubstituted isomers if necessary. If less than four steps area wons necessary enter "none" in the last box(es). A) KMNO4, H2O D) CH3CH2CH,CI, AICI3 G) N-bromosuccinimide, (PHCO2)2 J) HNO3, H2SO4 M) BH3, THF; then H2O2, "OH P) CH3CH2CI, AICI3 B) H2, Pd E) CH3CH,COCI, AICI3 H) CH3CI, AICI3 K) CH3COCI, AICI3 N) Br2, FeBr3 Q) CH3CHCICH3, AICI3 C) C2, FeCl3 F) Br2, CH2CI2 I) KOH, ethanol L) Fe, H30*, then OH O) SO3, H2SO4 R) LIAIH4, then H3O* HO, Reagents used:
- Provide the complete mechanism using curved arrow formalism for the reaction of p-isopropxlbenzoic acid undergoing nitration. Tell how many peaks in the 'H and 13C NMR spectrum that would be observed for the final product.B) Rank the following species in order of increasing nucleophilicity. (A) CH3CH2S-, (B) CH3CH2O-, (C) (CH3)3CO-, (D) (CH3)3COH.Identify whether the following mechanism is SN1, SN2, E1, E2, or E1cB or a combination. a. b. C. d. Br benzyl bromide Br benzyl bromide NaOEt in dry alcohol water in formic acid solution 3-iodocyclohexan-1-one 1-iodo-2,2-dimethylbutane NaOEt in EtOH Aa NaSCH3 OH E
