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This is because 2-chlorobutane possesses two different sets of β-hydrogens at the first and third carbons respectively, resulting in 1-butene or 2-butene. It is important to note that as a secondary alkyl halide, both E2 and Sn2 reactions are equally likely when reacting with a substance that can act as both a base and a nucleophile.
1-Chloro-2-butene, 1-chlorobut-2-ene, 2-butenyl chloride, gamma-methylallyl chloride. Identifiers CAS Number. 591-97-9 ...
In the similar substitution of 1-chloro-3-methyl-2-butene, the secondary 2-methyl-3-buten-2-ol is produced in a yield of 85%, while that for the primary 3-methyl-2-buten-1-ol is 15%. Allylic shifts occur because the transition state is an allyl intermediate.
The first step is the liquid- or vapour-phase chlorination of butadiene to a mixture of 3,4-dichlorobut-1-ene and 1,4-dichlorobut-2-ene (both isomers). In the second step, the mixture of 1,4-dichlorobut-2-ene and 3,4-dichlorobut-1-ene is isomerized to 3,4-dichlorobut-1-ene by heating to temperatures of 60–120 °C in the presence of a catalyst.
Very often, cis–trans stereoisomers contain double bonds or ring structures. In both cases the rotation of bonds is restricted or prevented. [4] When the substituent groups are oriented in the same direction, the diastereomer is referred to as cis, whereas when the substituents are oriented in opposing directions, the diastereomer is referred to as trans.
[2] The haloform reaction, using chlorine and sodium hydroxide, is also able to generate alkyl halides from methyl ketones, and related compounds. Chloroform was formerly produced thus. Chlorine adds to the multiple bonds on alkenes and alkynes as well, giving di- or tetra-chloro compounds.
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This may be seen in the reaction of 1-chloro-2-butene with sodium hydroxide to give a mixture of 2-buten-1-ol and 1-buten-3-ol: = = + = The Sn1CB mechanism appears in inorganic chemistry. Competing mechanisms exist. [7] [8]