a)
Interpretation:
The product formed during the SN2 reaction of 1-bromobutane with
NaI
Concept introduction:
In SN2 reaction the nucleophile plays a major role in the product formation. If a nucleophile is negatively charged then the product will be neutral. If a nucleophile is neutral then it results in the positively charge product.
b)
Interpretation:
The product formed during the SN2 reaction of 1-bromobutane with
KOH
Concept introduction:
In SN2 reaction the nucleophile plays a major role in the product formation. If a nucleophile is negatively charged then the product will be neutral. If a nucleophile is neutral then it results in the positively charge product.
c)
Interpretation:
The product formed during the SN2 reaction of 1-bromobutane with
CH≡CLi
Concept introduction:
In SN2 reaction the nucleophile plays a major role in the product formation. If a nucleophile is negatively charged then the product will be neutral. If a nucleophile is neutral then it results in the positively charge product.
d)
Interpretation:
The product formed during the SN2 reaction of 1-bromobutane with
NH3 is to be stated.
Concept introduction:
In SN2 reaction the nucleophile plays a major role in the product formation. If a nucleophile is negatively charged then the product will be neutral. If a nucleophile is neutral then it results in the positively charge product.
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Chapter 11 Solutions
Organic Chemistry
- Amines are converted into alkenes by a two-step process called Hofmann elimination. SN2 reaction of the amine with an excess of CH3I in the first step yields an intermediate that undergoes E2 reaction when treated with silver oxide as base. Pentylamine, for example, yields 1-pentene. Propose a structure for the intermediate, and explain why it readily undergoes elimination.arrow_forward1. Provide a mechanism for reaction below. 2. Why doesn't the reaction in either case, go through an SN2 mechanism.arrow_forwardv) What products would you expect if 2-butyne were treated with ozone in the presence ofacetic acidvi) What products would you expect if 1-butyne were treated with ozone in the presence ofacetic acidvii) What products would you expect if 2-butyne were treated with KMnO4 in the presenceof KOH in water?viii) What products would you expect if 1-butyne were treated with KMnO4 in the presence of KOH in waterarrow_forward
- What alkene would yield 2,2-dimethoxycyclopentane-1,3-dicarbaldehyde on treatment with O3 followed by (CH3)2S?arrow_forwardDeduce the structure of each compound from the information given. All unknowns in this problem have molecularformula C8H12.(a) Upon catalytic hydrogenation, unknown W gives cyclooctane. Ozonolysis of W, followed by reduction with dimethylsulfide, gives octanedioic acid, HOOC¬(CH2)6¬COOH. Draw the structure of Warrow_forwardA certain hydrocarbon, C7H10, yields the two products shown below upon oxidative cleavage with KMnO4/H3O+ . Deduce the structure of the hydrocarbon.arrow_forward
- A certain hydrocarbon, C5H6, yields the two products shown below upon ozonolysis with 1. O3/CH2Cl2 2. Zn/H3O . Deduce the structure of the hydrocarbon.arrow_forward-Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of -ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: (a) How many double bonds does -ocimene have? (b) Is -ocimene conjugated or nonconjugated? (c) Propose a structure for -ocimene. (d) Write the reactions, showing starting material and products.arrow_forwardWrite the mechanism of the hydrolysis of cis-5, 6-epoxydecane by reaction with aqueous acid. What is the stereochemistry of the product, assuming normal backside SN2 attack?arrow_forward
- When 5-bromo-1-pentanol is treated with sodium hydride in diethyl ether, the product is analyzed to be C5H10O. Propose a likely structure for this product, suggesting a reasonable mechanistic pathway for its formationarrow_forward1-Bromobutane would react with HS- via _______ reactiona.) SN1 b.) SN2 c.) E1 d.) E2arrow_forwardWrite out all the isomers of the compound with molecular formula C4H10O . Select the normal/ primaryisomer and treat it with conc. H2SO4 and heat. Identify the reaction and give the product ‘A’ from it. 2. When ‘A’ is treated with HBr in the presence of a peroxide, give the name and structure of the product.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning