(a)
Interpretation:
Major elimination product for given reaction if the product exists as stereoisomers is to be identified.
Concept Introduction:
Zaitsev’s Rule: States that the more substituted
(b)
Interpretation:
Major elimination product for given reaction if the product exists as stereoisomers is to be identified.
Concept Introduction:
Zaitsev’s Rule: States that the more substituted alkene is obtained when a hydrogen from is removed from the
(c)
Interpretation:
Major elimination product for given reaction if the product exists as stereoisomers is to be identified.
Concept Introduction:
Zaitsev’s Rule: States that the more substituted alkene is obtained when a hydrogen from is removed from the
(d)
Interpretation:
Major elimination product for given reaction if the product exists as stereoisomers is to be identified.
Concept Introduction:
Zaitsev’s Rule: States that the more substituted alkene is obtained when a hydrogen from is removed from the
(e)
Interpretation:
Major elimination product for given reaction if the product exists as stereoisomers is to be identified.
Concept Introduction:
Zaitsev’s Rule: States that the more substituted alkene is obtained when a hydrogen from is removed from the
(f)
Interpretation:
Major elimination product for given reaction if the product exists as stereoisomers is to be identified.
Concept Introduction:
Zaitsev’s Rule: States that the more substituted alkene is obtained when a hydrogen from is removed from the
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Chapter 9 Solutions
EBK ORGANIC CHEMISTRY
- 4. Give the starting alkene and any other reagents needed to selectively make the following compounds (with no organic byproducts!): OH L Eto OH all OH Br Br Brarrow_forward5. Subjection of 1-bromo-1-methylcyclopentane to the hydrolytic conditions shown leads to a mixture of products. Br -CH3 H₂O heat -CH3 OH -CH3 =CH₂ + H3O+ + Br A B с a. Which alkene do you expect to be most abundant in the product mixture? b. Provide a stepwise mechanism to explain how the alkene labeled C is formed. c. The reaction above is shown with hydronium ion (pK₂~-1.7) and bromide as products rather than HBr (pKa ~ -9). Use acid-base concepts to explain why HBr does not exist when there is an abundance of water.arrow_forwarda. What is the major monobromination product of the following reaction? Disregard stereoisomers. b. What is the anticipated percent yield of the major product (as a percentage of all the monobrominated products)?arrow_forward
- Pick the reactant or solvent in each part that gives the faster elimination reaction.a. reaction of -OH with 1-chloro-1-methylcyclohexane or 1-chloro-3-methylcyclohexaneb. reaction of H2O with CH3CH(Cl)CH2CH3 or (CH3)2C(Cl)CH2CH3c. reaction of (CH3)3CCl with -OH in H2O or DMSOarrow_forwardOH 1. Hg(OAc)2, H20 2. NaBH4 .CH3 CH3 H2C H3C Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H* adds to the sp2 carbon with the most hydrogens to yield the most stable carbocation intermediate, which then adds water to give the product alcohol. Because a carbocation intermediate is formed, rearrangements can occur prior to the addition of water. To avoid the possibility of rearrangement and still give a Markovnikov alcohol, alkenes can instead be treated with mercury(II) acetate in aqueous THF and then subsequently reduced with sodium borohydride. This reaction proceeds through a cyclic mercurinium ion intermediate which cannot rearrange. Water adds to the cyclic intermediate at the most substituted carbon to give an organomercury alcohol. The reduction step with sodium borohydride is complex and involves radicals. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing…arrow_forward9. Which compound will be converted more rapidly on treatment with H-Br : 1-butanol, 2-butanol, 2-methyl-1-butanol, or-2- methyl-2-butanol Please explain your answer.arrow_forward
- The following reaction can potentially produce three different cyclized products. 1. NaOMe, MeOH MeO cyclization products 2. acidic workup Provide the structures of the three cyclization products. Label the products as A, B, and C. Circle the major product. Five and six membered rings form preferentially over smaller and larger rings.arrow_forwardSelect the possible major product in the given reaction. 41. Dehydration of alcohols 42. Elimination of H-X in alkylhalides 43. Reaction of alcohols and carboxylic acids 44. Reduction of aldehydes 45. Substitution of reaction between ROH and SOCI, Choices: (A) 1 ROH (B) 2 ROH (C) 3 ROH (D) Alkene RCHO (E) (AB) RCOOH (AC) RCOR' (AD) RX Which of the following reagent (s) are needed in the following reactions? 46. Reduction of carboxylic acids to primary alcohols 47. Oxidation of primary alcohols to aldehydes 48. Reduction of ketones to secondary alcohols 49. Saponification of esters 50. Dehydration of alcohols Choices: aqueous NAOH and heat (B) Hạ in Pt (C) (A) H;O, H;SO, (D) H,SO, with heat (E) K,Cr,O, and H,So, (АB) LIAIH, (AC) PCC (AD) Tollens' reagentarrow_forwardWhich alkyl bromide(s) can form the alkene under E2 elimination conditions. Na CH,Br CH;CH,OH Br Br, Br в A C These molecules are unreactive B.arrow_forward