11. 1) Consider the two halves of the naphthalene as separate-which is more reactive? 2) Which position in the more reactive ring is most reactive? (There is only one major pdt.) OMe ळ con HNO3 12. Assume the kinetic product for sulfonylation unless otherwise indicated. O₂N H2SO4 (fuming)
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- (a) 2-methyl-2-pentanol Draw the structure of the alkene that was used to prepare the alcohol in highest yield. 8 ? ChemDoodleⓇ Which process does this employ? 1. Hg(OAc)2, H₂O; 2. NaBH4 1. BH3; 2. H₂O2, NaOH OsO4, H₂O2 #[ ] در On1. Which compound is expected to have a higher melting point, 1-pentanol or 1-pentanal? Explain 2. Which compound is expected to be more soluble in water, propanal or butanal? Explain. 3. Why is acetyl chloride more reactive towards hydrolysis than ethyl acetate?Draw the products formed when p-methylaniline (p-CH3C6H4NH2) is treated with each reagent.a. HClb. CH3COClc. (CH3CO)2Od. excess CH3Ie. (CH3)2C = Of. CH3COCl, AlCl3g. CH3CO2Hh. NaNO2, HCli. Part (b), then CH3COCl, AlCl3j. CH3CHO, NaBH3CN
- When toluene is treated with sulfuric and nitric acids under special conditions, three nitro (NO2) groups are substituted for hydrogens at the 2, 4 and 6 positions on the ring (the next section discusses why the 2, 4, and 6 positions are substituted). The product is a highly explosive substance called 2,4,6-trinitrotoluene. This subastance is commonly known by a three letter name. What is it?Wittig reactions with the following -chloroethers can be used for the synthesis of aldehydes and ketones. (a) Draw the structure of the triphenylphosphonium salt and Wittig reagent formed from each chloroether. (b) Draw the structural formula of the product formed by treating each Wittig reagent with cyclopentanone. Note that the functional group is an enol ether or, alternatively, a vinyl ether. (c) Draw the structural formula of the product formed on acid-catalyzed hydrolysis of each enol ether from part (b).#6 Draw the structure of the principal organic product from the reaction of benzyl bromide with sodium thiomethozide (CH3NaS)
- A certain hydrocarbon had the molecular formula C16H26 and contained two triple bonds. Ozonolysis gave CH3(CH2), CO₂H and HO₂CCH2CH2CH2CH2CO₂H as the only products. Draw a reasonable structure for this hydrocarbon. Click and drag to start drawing a structure. D:9. Hydrates, in which two -OH groups are connected to the same carbon, are not favorable except in a few cases. One case is: a) acetaldehyde c) acetone b) formaldehyde d) chloroform 10. The Wolff-Kishner reaction, in which an aldehyde or ketone is treated with NH2NH2 and KOH, is: a) an oxidation c) an SN2 reaction b) a reduction d) a hydration 11. Which of these is most likely to dissolve in 5% NaOH? a) 1-decanol b) decanal c) decanoic acid d) 2-decanone bu itcolf Draw tbeDraw the line-angle formula of the enol formed in the following alkyne hydration reaction and then draw the structural formula of the carbonyl compound with which this enol is in equilibrium. -C=CH 1. (sia)2BH 2. NaOH/H₂O₂ an enol carbonyl compound • You do not have to consider stereochemistry. • Draw both the enol and the carbonyl forms. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures using the sign from the drop-down menu. ChemDoodleⓇ <
- 10. The Wolff-Kishner reaction, in which an aldehyde or ketone is treated with NH2NH2 and KOH, is: a) an oxidation c) an SN2 reaction b) a reduction d) a hydration 11. Which of these is most likely to dissolve in 5% NaOH? a) 1-decanol b) decanal c) decanoic acid d) 2-decanone 12. The following compound forms a cyclic hemiacetal all by itself. Draw the structure of that hemiacetal.11.7_7 Which of the following conversions is essentially irreversible? A) The reaction of an aldehyde with a Grignard reagent. B) The reaction of a ketone with an alcohol. C) The reaction of an aldehyde with a 1° amine. D) The reaction of an alkene with water in the presence of acid catalyst. AGive the IUPAC names (including E,Z and R,S designations).