CHM 206 Expt 17 Report

An organic chemistry experiment involves a nucleophilic substitution (SN2) reaction using 1-iodobutane and 2-naphthoxide ion. The 2-naphthoxide ion is generated from 2-naphthol and sodium hydroxide in an ethanol solvent. The experiment includes steps like generating the nucleophile, conducting the SN2 reaction, and analyzing the product using 1H NMR spectroscopy. Question: Write the structure of the undesired side product if CH3CH2O‾ (ethoxide) reacts with 1-iodobutane.

This is an organic chemistry question. PLEASE SHOW STEP BY STEP! ALSO PLEASE INCLUDE ALL ELECTRON LONE PAIRS AND CHARGES FOR STRUCTURES IF NECESSARY! Make sure you include a detailed explanation of your answer.

Topic: Organic Synthesis Involving Amines:  Propose an organic synthesis for 4-bromo-3-nitrophenol.  To achieve this, you can use any common reagents of your choosing, and your sole carbon source is 4-bromobenzoic acid.  Be sure to describe your process in the discussion text box and also attach a sketch of the stepwise progression of your synthesis process. Hint, this can be done in six major steps shown as reaction arrows. Six major reaction arrows would give one starting material, five intermediates, and one product.

H NH₂ ཡིནྣཾ ༥ ཨ ཨནྡྷ༥ ༠ ཨི་ཝཱ, ཙ ཨ་ར༩ H NH3+ the acidity of the amine ion drives the reaction to shift toward the conjugate base of the carboxylic acid product. the resulting carboxylic acid ion is a weaker base than an acetate ion. O aldehydes are more reactive toward nucleophiles than ketones. Onucleophilic attack occurs preferentially at the less hindered carbon of the formyl group.

20:32 hydroxide 2. Using curved arrows, show the deprotonation mechanism of phenol with (OH). Also, provide the structure of the product of this deprotonation. Start answering this question by drawing the structure of phenol. Then hydroxide ion. Find your most reactive electrons and draw the curved arrow that shows where they would go to deprotonate phenol. Then "make a bond break a bond" write they question 3. Provide valid resonance structures for the product of the previous arrow(s) charge moving onto the ortho- and para positions. Use curved to show how the charge resonates to the next structure in your scheme. all the proper notations for depicting resonance. that show the in the structures Be sure to use Send a chat C

Write a reaction that could be carried out to synthesize 1-(4-methylphenyl)ethanol (reactants will be a combination of Grignard reagent and carbonyl compound).

Estrogens are female sex hormones, the most potent of which is B-estradiol. OH AYA Но B-Estradiol In recent years, chemists have focused on designing and synthesizing molecules that bind to estrogen receptors. One target of this research has been nonsteroidal estrogen antagonists, compounds that interact with estrogen receptors and block the effects of both endogenous and exogenous estrogens. A feature common to one type of nonste- roidal estrogen antagonist is the presence of a 1,2-diphenylethylene with one of the benzene rings bearing a dialkylaminoethoxyl substituent. The first nonsteroidal estrogen antagonist of this type to achieve clinical importance was tamoxifen, now an important drug in the treatment of breast cancer. Tamoxifen has the Z configuration shown here. NMeg A B NMeg ? ОН Tamoxifen Propose reagents for the conversion of A to tamoxifen. Note: The final step in this synthesis gives a mixture of E and Z isomers.

6. The reaction between aniline and nitrous acid at low temperature yields A) an N-nitroso amine B) a diazonium salt C) a nitrile D) an amine nitrite salt 7. An organic nitrogen compound, X, gives ammonia on warming with dilute aqueous sodium hydroxide, X could be A) ethanamide B) ethylamine C) phenylamine D) amino ethanoic acid

Draw the principal organic product for the reaction of 2-bromohexane with lithium in diethyl ether, followed by formaldehyde in diethyl ether, and then followed by dilute acid. Click and drag to start drawing a structure. X A G P

Answer all three parts plz. You are starting with three aryl bromides. They undergo a typical grignard reaction with magnesium metal and anhydrous ether (diethyl ether). Dry ice is then added to it and it is then cooled. Draw and label the names of the aryl carboxylic acids that will form for each. Part a) bromobenzene Part b) para-bromoanisole Part c) meta-bromoanisole

Enanthotoxin is an extremely poisonous organic compound found in hemlock water drop- wart, which is reputed to be the most poisonous plant in England. It is believed that no British plant has been responsible for more fatal accidents. The most poisonous part of the plant is the roots, which resemble small white carrots, giving the plant the name"five finger death."Also poisonous are its leaves, which look like parsley. Enanthotoxin is thought to interfere with the Nat current in nerve cells, which leads to convulsions and death. он How many stereoisomers are possible for enanthotoxin?

Upon completion of a chemical reaction, you find you have a mixture of benzoic acid and ethyl benzoate. Propose a procedure to separate the ethyl benzoate from the mixture. You should look up the structures of benzoic acid and ethyl benzoate.

19. Propose an efficient synthesis of benzaldehye from toluene. Write complete equations showing the structure of all reactants and products for each step.

4) Write the reaction between cyclohexanecarboxylic acid and thionyl chloride showing all three products (two gaseous and one liquid). Take the liquid product and treat it with 2 moles of dimethylamine in benzene as the solvent. You get two products. What are they? Draw their formulae and write their names.

Black powder (see introduction) was the propellant used in rifles and pistols during the 1860’s.  Would it have been possible to use diphenylamine to detect gunshot residue on John Wilkes Booth after the assignation of President Lincoln?  Why or Why not?

POST-LABORATORY QUESTIONS 1. Effective mosquito repellents contain DEET (N,N-diethyl-3-methylbenzamide). If you were to synthesize this compound, with what carboxylic acid and amine would you start? Draw their structures. CH3 DEET O C-N CH₂CH3 CH₂CH3 H3C Metadone 2. Metadone, a narcotic analgesic (shown below as the amine), is dispensed as its hydrochloride salt. Explain the use of the salt rather than the amine. Use the structure shown and convert it to the hydrochloride salt. N-CH3 ogged

11) Synthesize 2-methyl-3-hydroxycyclohexone from cyclohexone, methyl iodide, and inorganic precursors.