How can you form a haloalkane from an alkene (4)?
From an alkyne (2)?
From an alkane (1)?
From an alcohol (3)?
From an ether (1)?
From an alkene:
1. addition of HX to alkene
2. addition of Br2 and Cl2
3. Allylic Bromination using NBS
4. (Non-Mark)- addition of HBr using peroxides
From an alkyne:
1. Bromination (2mol)
2. Addition of HX (2mol)
From an alkane:
1. radical bromination using heat or UV light
From an alcohol:
1. react with HBr (excess acid)
2. react with PBr3 (SN2 mechanism)
3. React with SOCl2 or SOBr2
From an ether:
1. acid catalyzed cleavage of dialkyl ethers (excess acid)
How do you form a hydroperoxide from an alkene?
autoxidation (peroxide and Br2)
How do you form an Markovnikov alcohol from an alkene?
1. Addition of HOCl and HOBr
2. Oxymercuration reduction
3. acid catalyzed hydration
How do you form an anti-Markovnikov alcohol from an alkene?
Hydroboration oxidation
What 2 ways can you use to form a diol?
1. acid catalyzed hydrolysis of an epoxide
2. oxidation of an alkene using osmium tetroxide
How can you form carboxylic acid?
oxidation of a primary alcohol using PCC
What are the 2 ways to form an epoxide?
1. intramolecular SN2 reaction with halohydrin
2. oxidation through MCPBA
What are 3 ways to make an ether?
1. Williamson ether synthesis
2. acid catalyzed dehydration of two alcohols
3. acid catalyzed addition of alcohols to alkenes
How can you make a cis-alkene vs. a trans alkene?
cis-hydrogenation of alkyne using Lindlar catalyst
trans-reduction using Na and NH3(l)
How can you extend the C-C chain?
1. use acetylide ion for SN2 reaction with alkyl halide
2. Organomag/lith- open up epoxide rings (extended by 2 carbons)
3. organocopper- can react with other alkyl halides like acetyides
How do you make an alkyne?
bromination of an alkene to yield tetrahaloalkane; then dehydrohalogenation using strong base
How do you make an alkane from an alkyne?
from an alkene?
From an alkyne:
1. hydrogenation using Pd/Pt/Ni
From an alkene:
1. hydrogenation using Pd/Pt/Ni
2. Enantioselective reduction using Ru-Cl3
How can you form carbonyl groups? (encompasses aldehydes/ketones)
1. keto-enol tautomerism
2.hydroboration-oxidation of alkyne (yields aldehyde)
3. ozonolysis of an alkene
4. acid catalyzed hydration of an alkyne (yields ketone)
5. Pinacol rearrangement
6. Oxidation of diols using periodic acid
How do you form an alkene?
acid catalyzed dehydration