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Chemistry Advanced Level Notes

The document covers advanced organic chemistry topics including reaction mechanisms such as electrophilic aromatic substitution and nucleophilic aliphatic substitution. It also discusses stereochemistry concepts like chirality and stereoisomerism, along with advanced synthesis techniques like cross-coupling reactions and olefin metathesis. Additionally, it highlights key concepts such as regioselectivity and chemoselectivity, as well as advanced topics like click chemistry and green chemistry.

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Shaheer Mujtaba
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12 views3 pages

Chemistry Advanced Level Notes

The document covers advanced organic chemistry topics including reaction mechanisms such as electrophilic aromatic substitution and nucleophilic aliphatic substitution. It also discusses stereochemistry concepts like chirality and stereoisomerism, along with advanced synthesis techniques like cross-coupling reactions and olefin metathesis. Additionally, it highlights key concepts such as regioselectivity and chemoselectivity, as well as advanced topics like click chemistry and green chemistry.

Uploaded by

Shaheer Mujtaba
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as RTF, PDF, TXT or read online on Scribd
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Advanced Organic Chemistry Notes

Reaction Mechanisms

- Electrophilic Aromatic Substitution: Electrophilic aromatic substitution is a


reaction mechanism that involves the substitution of an electrophile for a
substituent on an aromatic ring. For example, the nitration of benzene involves
the substitution of a nitro group (-NO2) for a hydrogen atom on the benzene ring.

C6H6 + HNO3 → C6H5NO2 + H2O

- Nucleophilic Aliphatic Substitution: Nucleophilic aliphatic substitution is a


reaction mechanism that involves the substitution of a nucleophile for a leaving
group on an aliphatic carbon. For example, the reaction of 1-bromopropane with
sodium hydroxide involves the substitution of a hydroxide ion (-OH) for the
bromine atom.

CH3CH2CH2Br + NaOH → CH3CH2CH2OH + NaBr

Stereochemistry

- Chirality: Chirality is the property of a molecule that makes it non-


superimposable on its mirror image. For example, the molecule 2-butanol is chiral
because it has a stereocenter (the carbon atom bonded to the -OH group) and its
mirror image is not superimposable.

CH3CH(OH)CH2CH3
- Stereoisomerism: Stereoisomerism is the phenomenon where molecules with
the same molecular formula and bond sequence have different three-dimensional
arrangements of atoms. For example, the molecule 1,2-dichlorocyclohexane has
two stereoisomers: cis-1,2-dichlorocyclohexane and trans-1,2-
dichlorocyclohexane.

Advanced Synthesis

- Cross-Coupling Reactions: Cross-coupling reactions are a class of reactions that


involve the formation of a carbon-carbon bond between two organic molecules.
For example, the Suzuki-Miyaura reaction involves the coupling of an aryl halide
with an aryl boronic acid.

C6H5Br + C6H5B(OH)2 → C6H5-C6H5 + B(OH)3

- Olefin Metathesis: Olefin metathesis is a reaction that involves the exchange of


alkylidene fragments between two alkenes. For example, the reaction of 1-hexene
with a ruthenium catalyst involves the formation of a new alkene and a new
alkylidene fragment.

CH2=CH(CH2)4CH3 → CH2=CH(CH2)3CH3 + CH2=CHCH3

Key Concepts

- Regioselectivity: Regioselectivity is the preference for a reaction to occur at one


location in a molecule over another. For example, the reaction of 1-
methylcyclohexene with HCl can result in two different products, depending on
which carbon atom the hydrogen atom adds to.
- Chemoselectivity: Chemoselectivity is the preference for a reaction to occur with
one functional group over another. For example, the reaction of a molecule
containing both an alkene and an alkyne with a reducing agent can result in the
selective reduction of one functional group over the other.

Advanced Topics

- Click Chemistry: Click chemistry is a modular approach to synthesizing complex


molecules using simple, efficient reactions. For example, the Huisgen
cycloaddition reaction involves the coupling of an alkyne with an azide to form a
triazole ring.

RC≡CH + R'N3 → R-C=N-N(R')-N

- Green Chemistry: Green chemistry is a field of chemistry that focuses on the


design of products and processes that minimize environmental impact. For
example, the use of supercritical carbon dioxide as a solvent in chemical reactions
can reduce the amount of organic solvent waste generated.

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