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Organic Chemistry 328 SI
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When reacting aniline with Br2 / FeBr3, what product forms?
Both I and III
Rank the following in order of increasing activation. (Deactivators first)
II < III < I < IV
IV < I < III < II
II < I < III < IV
II < IV < I < II
Which compound is most reactive for electrophilic aromatic substitution?
Similar to table 16.1
Nucleophilic Aromatic Substitution
Classify this reaction
Electrophilic Aromatic Substitution
Both B and C
What is a reactive intermediate of addition-elimination?
None of these form
Occurs with strong nucleophiles and some weak
Ex: -OH, -OR, -NH2, -SR, NH3, RNH2
Which compound is most reactive for addition-elimination?
None are reactive
-OH, -OR, -NH2, -SR and some neutral (NH3 and RNH2)
Addition of a nucleophile
Elimination of a leaving group
Strong electron-withdrawing groups (-NO2)
Ortho or para position to the halogen
Increasing the electronegativity of the leaving group
Aryl fluorides (ArF)
Which compound is most reactive for an addition-elimination reaction?
Both II and IV
WHICH STATEMENT IS FALSE REGARDING ELIMINATION-ADDITION NUCLEOPHILIC AROMATIC SUBSTITUTIONS?
These reactions require very harsh conditions (300˙c, 170 atm)
A very unstable benzyne intermediate is formed during this reaction
The first step of this mechanism involves the elimination a hydrogen and a halogen on two adjacent carbons
This substitution reaction mechanism parallels a SN1 reaction mechanism
A mixture of products can occur
1. NaOH, 300˚C, 170 atm 2. H3O+ (Aryl halide => phenol)
NaNH2 / NH3+ (Aryl halide => aniline)
Formation of a benzyne (an intermediate)
Substitution on carbon bonded to halide or adjacent carbon
What’s the product?
II and III
When reacting m-chlorotoluene with KOH at 300˙C would yield what?
I and II
All of these would form.
What is the product?
None of these.
Oxidation of Substituted Rings
KMnO4 or O2 / Co(III)
Oxidizes benzylic carbon to carboxyl group
Thus forms benzoic acid
Only on primary, secondary, or tertiary carbons
No reaction for quandary carbons –C(CH3)3
Halogenation of Alkyl Benzenes
Adds a Bromine to the benzylic carbon
Br2 / hv or ∆
NBS / hv or ROOR
Reactive intermediate: resonance stabilized benzylic radical
Product: Benzylic halide
Benzene is reacted with: 1. ClCOH / AlCl3 2. H2 / Pd-C What is the product?
Reduction of Substituted Rings
Substituent Reduction Reagents:
Zn (or Hg) + HCl (Strong acid) / ∆
Replaces C–O bonds with C–H bonds on benzylic carbon
KOH (strong base) / ∆
H2 / Pd
Reduction of benzene to cyclopentane:
H2 / Rh/C catalyst
1. Fe, H3O+ 2. –OH
Reduction of Nitro Groups
Converts Nitrobenzene => aniline
1. Fe, H3O+ 2. -OH
Which step contains a flaw or would not occur?
Fe, H3O+ / -OH
All work just fine!
What forms from a benzene mixed with this reagent sequence?
CH3CH2CH2Cl / AlCl3
HNO3 / H2SO4
Fe / HCl
NBS / ROOR
III and IV
Starting with a benzene, generate a reagent scheme to produce styrene.
Many different ways.
1. CH3CH2Cl / AlCl3 2. NBS / (BzO)2CCl4 3. Potassium tert-butyloxide
Name this molecule.
What is the IUPAC name?
Which step contains a flaw or would not occur