
Interpretation:
To explain why (CH3)2CHCH(Br) CH2CH3 reacts faster than (CH3)2CHCH2CH(Br) CH3 in an E2 reaction.
Concept introduction:
The most common mechanism for dehydrohalogenation is the E2 mechanism. An E2 reaction exhibits a second-order kinetics, in which the reaction is bimolecular and both the
The transition state of an E2 reaction consists of four atoms from the alkyl halide-one hydrogen atom, two carbon atoms, and the leaving group (X)-all aligned in the same plane. There are two ways for the C-H and C-x bonds to be coplanar. When the H and X atoms oriented on the same side of the molecule. This geometry is called syn periplanar. While the H and X atoms oriented on opposite sides of the molecule. This geometry is called anti periplanar. The dihedral angle for the C-H and C-X bonds equals 0° for the syn periplanar arrangement and 180° for the anti periplanar arrangement.

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Chapter 8 Solutions
Organic Chemistry
- Determine if the following salt is neutral, acidic or basic. If acidic or basic, write the appropriate equilibrium equation for the acid or base that exists when the salt is dissolved in aqueous solution. If neutral, simply write only NR. Be sure to include the proper phases for all species within the reaction LiNO3arrow_forwardAn unknown weak acid with a concentration of 0.410 M has a pH of 5.600. What is the Ka of the weak acid?arrow_forward(racemic) 19.84 Using your reaction roadmaps as a guide, show how to convert 2-oxepanone and ethanol into 1-cyclopentenecarbaldehyde. You must use 2-oxepanone as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way. & + EtOH H 2-Oxepanone 1-Cyclopentenecarbaldehydearrow_forward
- R₂ R₁ R₁ a R Rg Nu R₂ Rg R₁ R R₁₂ R3 R R Nu enolate forming R₁ R B-Alkylated carbonyl species or amines Cyclic B-Ketoester R₁₁ HOB R R₁B R R₁₂ B-Hydroxy carbonyl R diester R2 R3 R₁ RB OR R₂ 0 aB-Unsaturated carbonyl NaOR Aldol HOR reaction 1) LDA 2) R-X 3) H₂O/H₂O ketone, aldehyde 1) 2°-amine 2) acid chloride 3) H₂O'/H₂O 0 O R₁ R₁ R R₁ R₁₂ Alkylated a-carbon R₁ H.C R₁ H.C Alkylated methyl ketone acetoacetic ester B-Ketoester ester R₁ HO R₂ R B-Dicarbonyl HO Alkylated carboxylic acid malonic ester Write the reagents required to bring about each reaction next to the arrows shown. Next, record any regiochemistry or stereochemistry considerations relevant to the reaction. You should also record any key aspects of the mechanism, such as forma- tion of an important intermediate, as a helpful reminder. You may want to keep track of all reactions that make carbon-carbon bonds, because these help you build large molecules from smaller fragments. This especially applies to the reactions in…arrow_forwardProvide the reasonable steps to achieve the following synthesis.arrow_forwardIdentify which compound is more acidic. Justify your choice.arrow_forward
- Provide the reasonable steps to achieve the following synthesis.arrow_forwardWhen anisole is treated with excess bromine, the reaction gives a product which shows two singlets in 1H NMR. Draw the product.arrow_forward(ii) Draw a reasonable mechanism for the following reaction: CI NaOH heat OH (hint: SNAr Reaction) :arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
