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- Which of the following substances would undergo the haloform reaction? Explain. (c) CHỊCH,CHO (a) CH3COCH3 (d) CH3CO₂H (b) Acetophenone (e) CH3C=NHow will you synthesize cyclohexanecarboxaldehyde (cyclohexylmethanal) from the following reagents? (There are no restrictions on the reagents or the number of steps). (a) Cyclohexanone (b) Ethynylcyclohexane (c) Methyl cyclohexylformate (Remember: Formic acid is the IUPAC recognized name for Methanoic acid) (d) Cyclohexanecarboxylic acid (Cyclohexylmethanoic acid) (e) Vinylcyclohexanegas, Cl¬CH2CH2¬S¬CH2CH2¬Cl, was used as a poisonous chemical agentin World War I. Mustard gas is much more toxic than a typical primary alkyl chloride. Itstoxicity stems from its ability to alkylate amino groups on important metabolic enzymes,rendering the enzymes inactive.(a) Propose a mechanism to explain why mustard gas is an exceptionally potent alkylatingagent.(b) Bleach (sodium hypochlorite, NaOCl, a strong oxidizing agent) neutralizes and inactivates mustard gas. Bleach is also effective on organic stains because it oxidizes coloredcompounds to colorless compounds. Propose products that might be formed by thereaction of mustard gas with bleach.
- The following compound, 2-hydroxycycloheptatrienone, does not give all the usual carbonyl group reactions. (i) Explain this apparent anomaly. Furthermore, explain the significant difference between the relative stability of this compound and its 3- and 4-hydroxy isomers. (ii) What would you expect to be the influence of adding (a) a nitro group as a substituent on the 7-membered ring or (b) an alkyl group, on the degree of aromaticity of the above compound. (iii) Based on your understanding of the hydrogen bonding concept, which isomer would you expect to have a higher m.p, (assuming they are both solids) between 2- and 4- hydroxycycloheptatrienone? Explain your choice.Predict the product(s) and show the complete electron-pushing mecha- nism for each of the following dissolving metal reductions. (a) H3CC=CCH₂CH3 (b) (c) CECH 1844 Li NH3 ND3 C=C—CH3 NH32) Identify whether each of the following reaction performs a SN1, SN2, E1 or E2; Then, draw the appropriate products. Meo (a) NH2 (d) Br Br он (b) (e) ELOH HO Br (c) (f) Br
- Give the products for each of the following reactions. (a) (b) (c) + H₂cod OCH3 о || -COCH 3Show how you would convert hex-1-ene to each of the following compounds. You may use any additional reagents andsolvents you need.( (b) 1-methoxyhexaneConsider the tetracyclic aromatic compound drawn below, with rings labeled as A, B, C, and D. (a) Which of the four rings is most reactive in electrophilic aromatic substitution? (b) Which of the four rings is least reactive in electrophilic aromatic substitution? (c) What are the major product(s) formed when this compound is treated with one equivalent of Br2?
- Rewrite each of the following stereospecific transforms as a synthetic step in the forward direction, including reagents and any special reaction conditions. (a) (b) OH "CH3 CH3 H (Racemic) (c) OH (d) CN Br (Racemic) BrPredict the product(s) and provide the mechanism for each of the following reactions. (a) (b) LOCH₂CH3 HI HBr ? ?Provide the major organic product for each of the following transformations. 1) LIAIH4 2) H* -NH2 он но trace H* н" NH (CgHs)3P*-CH2 trace H*