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Lecture 9. Alkyl Halides

Alkyl halides are compounds with halogen atoms bonded to saturated sp3-hybridized carbon atoms, characterized by their general structure Rx. The document outlines the steps for naming alkyl halides, their preparation methods from alcohols, and various reactions including nucleophilic substitution (SN1 and SN2) and elimination reactions (E1 and E2). Key concepts such as bond length and strength variations, as well as the Zaitsev rule, are also discussed.

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112 views10 pages

Lecture 9. Alkyl Halides

Alkyl halides are compounds with halogen atoms bonded to saturated sp3-hybridized carbon atoms, characterized by their general structure Rx. The document outlines the steps for naming alkyl halides, their preparation methods from alcohols, and various reactions including nucleophilic substitution (SN1 and SN2) and elimination reactions (E1 and E2). Key concepts such as bond length and strength variations, as well as the Zaitsev rule, are also discussed.

Uploaded by

Aira Mae Poquiz
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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ALKYL HALIDES

OLFU | College of Medical Laboratory Science


ALKYL HALIDES
➢ Compounds containing halogen bonded to a saturated sp3-hybridized carbon atom
➢ General structure = Rx (R=alkyl group, and may have multiple bonds and cyclic structure;
x=any halides or halogens, and can have multiple halogens)

➢The halides is
connected single
bonded to the carbon
Steps in Naming Alkyl Halides STEPS:
1. Find the Parent Hydrocarbon
✓Include the multiple bond/s if present

2. Number the atoms in the parent chain


✓Substituents must have the lowest possible number
✓Use prefixes applicable
✓Put the substituents in alphabetical order
➢May have halogens as substituents
3. Write the name
Structure of Alkyl Halides
❖As you go down the periodic table,
❖R-X bond length is ___________
increasing
❖R-X bond strength is ___________
decreasing
(Making, creating, or synthesizing)
Preparation of Alkyl Halides
is the product

Preparing Alkyl Halides


❖Synthesis of alkyl halides from alcohols
➢A. Reaction of tertiary alcohol with HX
➢B. Reaction of primary and secondary alcohol with PBr3 and SOCl2
Reactions of Alkyl halides
is the reactant

I. Formation and protonation of Grignard reagents


❖Grignard Reagents
✓ Alkyl halides react with Magnesium metal in ether solvent to yield organo-
magnesium halides.

Alkyl halide (RX) is the starting point


II. Nucleophilic Substitution Reaction
❖SN2 reaction
✓ The entering nucleophile attacks the substrate from a direction 180º away from the
leaving group, resulting in an umbrella-like inversion of configuration at the C atom.
✓ Fast replacement
✓ 2 means that the substrate (alkyl halide) and the reagent directly affects the product

❖SN1 reaction
✓ Occurs by spontaneous loss of the leaving group before the incoming nucleophile
approaches. Loss of the leaving group gives a carbocation intermediate, which then
reacts with nucleophile in a second step to yield the substitution product.
✓ slow replacement
✓ Only the substrate (alkyl halide) will affect the product
III. Eliminations
❖E2 reaction
✓ Base abstracts a proton at the same time that the leaving group departs.
✓ Remove the x (halide)
✓ Produces double bond
✓ 2 means that the substrate (alkyl halide) and the reagent directly affects the product

❖E1 reaction
✓ the substrates spontaneously dissociates to form a carbocation, which can subsequently lose H+ from a neighboring
carbon.
✓ Only the substrate (alkyl halide) will affect the product

❑ Zaitsev rule – the more balanced


carbon you have, the better

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