ochem 2 lab final

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maleic anhydride + anthracene

"endo" diels-alder adduct

aldol reaction

-2 of C6H5CHO and 1 C5H8O -heat up with magnetic stirring bar

esters, synthesis of aspirin

-acetylsalicyclic acid (aspirin) -dont exceed temp (70-80C) in hot water bath twice.

anthracene

-aromatic hydrocarbon -diene when reacting maleic anhydride

dilantin step 1

-benzaldehyde to benzoin -just mix together and leave a week -NaOH to react with HCl and release thiamine

dilantin step 3

-benzil to dilantin -reflux

dilantin step 2

-benzoin to benzyl -reflux

polystyrene production

-heat in fume hood over metal block

polyurethane production

-just mix together -foam

nylon production

-mix together then grab out solid

which bromine in 1,2-dibromo-4-nitrobenzene would be substituted by a nucleophile

1-bromo would be substituted because it is in the para position and due to the movement of electrons it is the easiest way instead of the meta position

how to calculate the theoretical yield

1. take limiting reactant and both will be mol of limiting 2. add MW of both reactants together 3. multiply together to get grams

following progress of reaction by TLC in esterification

3 lanes would be spotted with different mixtures to help analyze the reaction. after some time you can observe under UV light how well the reaction worked by comparing it to others

phenol with Br reacts with aniline, EtOH/H2O

Br replaced by aniline attached at NH

phenol with Br reacts with CH3CH2NH2, EtOH/H2O

Br replaced with Nh2CH2CH3 at NH

phenol with Br reacts with KSCN, EtOH/H2O

Br replaced with SCN

how do you account for smell of vinegar when an old bottle of aspirin is opened

H2O enters eveytime you open bottle which begins hydrolysis reaction which creates acetic acid which smells like vinegar

source of acid that catalyzes esterification

H2SO4

HCl is as strong a mineral acid as H2SO4. why would it not be satisfactory catalyst for this reaction

H2SO4 is also a dehydrating agent, therefore, forces equilibrium to right and produces more products

purpose of washing ether solution of product with 5% NaHCO3 solution in esterification

NaHCO3 will remove the unreactive benzoic acid and help make the compound pure

chemical equation showing formation of aspirin from salicyclic acid and acetic anhydride

SA-Nu AA-E

saponification

The hydrolysis of an ester in the presence of a base. -irreversible

what is a meisenheimer complex

a 1:1 reaction between an arene carrying an electron withdrawing group and a nucleophile

esters made by

alcohols or phenols with organic or inorganic acids

what organic functional group do nylon and proteins have in common

amide

what does it mean to say that aspirin is an analgesic and an antipyretic

analgesic reduces pain and antipyretic lowers body temp. aspirin does both

rxn between urea and isocyanic acid strongly favors urea, why does it still go to completion?

because urea replenishes the isocyanic acid consumed

Cu2+ blue and Cu+ yellow, how do you account for color changes observed during oxidation of benzoin to benzil

copper used for oxidation starts out as Cu2+ and converted to Cu+ by NH4NO3

maleic anhydride

dienophile -limiting reactant based on MW into mmol

nucleophilic aromatic substitution

done in microwave -1980 -yellow to light yellow

common large scale use of both urea and ammonium nitrate

fertilizer

what causes solution to foam and expand in volume during polyurethane production

formation of gas

reflux

heating the chemical reaction for a specific amount of time, while continually cooling the vapour produced back into liquid form, using a condenser. -diels-alder reaction uses

advantage of generating a reagent in situ

in situ allows slow release of reagent and can control rate of reaction

2 things you could do to improve yield of esterification

increase conc of alcohol or CA to shift equilibrium to the right

why is 2,5-dibenzalcyclopentanone yellow?

it is highly conjugated, therefore energy state is in the range where molecule can absorb visible color and leaves yellow for us to see

would methanol or hexane be a better solvent when using microwaves to heat a reaction mixture

methanol is polar which works well with microwaves, therefore, the substance would heat quicker and better. Hexane is nonpolar and doesnt heat well

purpose of Na2CO3 in synthesis of nylon

neutralizes HCl allowing further bonding to take place

what types of reactants are needed for successful crossed aldo reaction

one molecule needs to be able to form an enolate ion and the other should be able to form alpha bonds and have no alpha hydrogens

synthesis of dulcin

p-phenetidine (p-ethoxyaniline) with isocyanic acid (by urea) -reflux

closer melting point is to theoretical melting point

purer the product

methyl benzoate by fischer esterification

reflux

hydrolysis of esters

reversed reaction of making esters -ester reacts with water

dulcin is artificial sweetener but can be toxic in large amounts because

starts converting to p-aminophenol in the body

why styrene soluble in toluene but not ethanol

styrene and toluene both non-polar. ethanol is polar

why do you need to grease joint between condensor and flask in dilantin synthesis

they become stuck after reflux and hard to separate

explain why the two sets of nitrogen protons in the H NMR spectrum of dulcin have such different chemical shifts

theyre connected to different atoms. one is amide and other is connected to two C's. gives a difference in shielding factors.

why is cold solvent used to wash product rather than room temp or hot solvent in Nu subs rxn

to prevent the exothermic or endothermic reaction from happening with 2 or more reactants

following progress of reaction by IR spectroscopy in esterification

use pure reactant and reactant mixture then obtain graphs and analyze

why is water detrimental to acid catalyzed esterification

water reacts with product of ester to hydrolyze it back to acid and alcohol. ensures reversibility

why does the initial yellow color of the reaction fade during the diels-alder reaction?

when the substance is heated, conjugated bonds are broken up which causes the color to fade


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