a)
Interpretation:
The product formed when 2-hexyne reacts with 2 equivalents of bromine.
Concept introduction:
In addition reactions,
To give:
The product formed when 2-hexyne reacts with two molar equivalents of bromine.
b)
Interpretation:
The product formed when 2-hexyne reacts with 1 equivalent of HBr is to be predicted.
Concept introduction:
In addition reactions, alkynes when treated with two molar equivalents of a reagent yield the derivatives of the corresponding alkane as the product. With one molar equivalent of a reagent they yield a derivative of the corresponding alkene as the product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.
To predict:
The product formed when 2-hexyne reacts with 1 equivalent of HBr.
c)
Interpretation:
The product formed when 2-hexyne reacts with 1 equivalent of HBr is to be predicted.
Concept introduction:
In addition reactions, alkynes when treated with excess amount of a reagent yield the derivatives of the corresponding alkane as the product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.
To predict:
The product formed when 2-hexyne reacts with excess of HBr.
d)
Interpretation:
The product formed when 2-hexyne reacts with Li in ammonia.
Concept introduction:
Alkynes can be reduced by treatment with hydrogen in the presence of a catalyst. The hydrogenation occurs with anti stereochemistry to give a trans- alkene as product if Li in ammonia is used.
To predict:
The product formed when 2-hexyne reacts with Li in ammonia.
e)
Interpretation:
The product formed when 2-hexyne reacts with H2O, H2SO4 in the presence of HgSO4 is to be given.
Concept introduction:
When treated with H2O, H2SO4 in the presence of HgSO4 alkynes get hydrated to produce enols. The addition of water to unsymmetrical alkynes follows Markonikov regiochemistry while it cannot be applied in the case of symmetrical alkynes. The enols produced then undergo tautomerization to give a
To predict:
The product formed when 2-hexyne reacts with H2O, H2SO4 in the presence of HgSO4.
Trending nowThis is a popular solution!
Chapter 9 Solutions
ORGANIC CHEMISTRY-EBOOK>I<
- 4 Predict the products of reactions of ethers and epoxides, including the following:(a) Cleavage and autoxidation of ethers(b) Acid- and base-promoted opening of epoxides(c) Reactions of epoxides with organometallic reagents(d) Cleavage of silyl ethersarrow_forwardWhat product will be formed? Hg(OAc), NaBH4, HO- -? TsCl, pyridine KCN IH ICN (a) (b) CN IOTS (a) (b)arrow_forwardElectrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict themajor products of the reactions of naphthalene with the following reagents.(a) HNO3, H2SO4 (b) Br2, FeBr3 (c) CH3CH2COCl, AlCl3arrow_forward
- Devise a synthesis of (E)-tetradec-11-enal, a sex pheromone of the spruce budworm, a pest that destroys fir and spruce forests, from acetylene, Br(CH2)10OH, and any needed organic compounds or inorganic reagents.arrow_forwardWhat reagents would you use to carry out the following reaction? (A) H₂ / Pt (B) (C) (D) H₂/Lindlar's ??? Li, EtNH₂ followed by NH4Cl H₂O₂ / NaOHarrow_forwardWhich of the following compounds are generated by the reaction below? он (1) Hg(OAc)2, H20 но. (2) NaBHalethanol OH (A) (B) (C) (D) Compounds A, C and D O Compound B Compounds B and D O Compounds A and D (0)arrow_forward
- If anhydrides react like acid chlorides with the nucleophiles, draw the products formed when each of the following nucleophiles reacts with benzoic anhydride [(C6H5CO)2O]: (a) CH3MgBr (2 equiv), then H2O; (b) LiAlH4, then H2O; (c) LiAlH[OC(CH3)3]3, then H2O.arrow_forwardDraw the main organic product formed in each of the following reactions: (a) (b) (c) + HNO3 / H₂SO4 O CI CI AICI 3 AICI3arrow_forwardPredict the products of the following reaction HBr (1 equiv.)arrow_forward
- Devise a synthesis of (E)-tetradec-11-enal, a sex pheromone of the spruce budworm, a pest that destroys r and spruce forests, from acetylene, Br(CH2)10OH, and any needed organic compounds or inorganic reagents.arrow_forwardон Mẹ 4. HSO4 → Product and name of the reaction is : NH – C – Me NH – C – Me (Hoffmann bromamide reaction) (Beckmann rearrangement) (а) (b) CN (c) (Curtius reaction) (d) None of thesearrow_forwardCH3 NH3, H* H3C H3C CH: Substituted pyrroles are often prepared by treatment of a 1,4-diketone with ammonia in the presence of catalytic H*. The mechanism involves the following steps: 1) Protonation of the carbonyl oxygen and nucleophilic attack by ammonia form tetrahedral intermediate 1; 2) Proton transfer leads to protonated carbinolamine 2; 3) B-elimination leads to enamine 3; 4) Protonation of the carbonyl oxygen and nucleophilic attack by the amine form tetrahedral intermediate 4; 5) Proton transfer leads to protonated carbinolamine 5; 6) B-elimination leads to the final product. Write out the reaction mechanism on a separate sheet of paper, and then draw the structure of tetrahedral intermediate 4. • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. Do not include lone pairs in your answer. ZIarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning