Essay on Che113 Exam 1 Review 1 1

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Chemistry 113
Exam 1 Review

Starting with benzene, determine what product(s) you would form using the following reagents: You may need one, two or three different combinations to obtain a product.

KMnO4, H3O+

ClCO(CH2)2CH3, AlCl3

Br2, FeBr3

CH3CH2CH2CH2Cl, AlCl3

Cl2, FeCl3

H2/Pd

CH3Cl, AlCl3

NBS, peroxides

HNO3, H2SO4

(CH3)3CCH2Cl

Be prepared to identify all aromatic activators and deactivators, in addition to the ring positions each affects.
Various substances discussed in lecture have acidic characteristics. Given a list of substances, be prepared to determine which is most or least acidic.
Various substances discussed in lecture have characteristics that affect the boiling point. Given a list of substances, be prepared to determine which has the highest or lowest boiling point.
Given a monosubstituted benzene ring and a reagent, be prepared to determine what the product(s) will be, based on your knowledge of activators and deactivators. For example: If you start with halogenated toluene, what will be produced by treatment with a mixture of nitric and sulfuric acid? Note: this is one example. Go through the lecture slides and know all examples given.
You should be able to organize benzene and a variety of monosubstituted benzene derivatives into order of increasing reactivity to electrophilic aromatic substitution.
Be prepared to analyze the reactants and products associated with Friedel-Crafts alkylation and acylation.
What reagent would you use to produce a ketone from cyclohexanol?
What reagent would you use to produce 1-methylcyclohexene from 1-methylcyclohexanol?
What reagent would you use to produce an epoxide from 1-methylcyclohexene?
How would you convert the above epoxide into a compound that contains both a hydroxyl and an ether?
Cr(VI) species are oxidizing agents. What products are produced with these reagents when the starting materials are alcohols? (Recall that there are different classifications of alcohols).
Be prepared to analyze the Williamson ether synthesis and intramolecular Williamson synthesis.
Can an aldehyde be prepared from an alcohol? If so, can you write the structure of the reactant and product? Is there a reagent that will work for this reaction?
Given…