Interpretation:
Looking at the possible catrbocation intermediates produced during the addition of HCl to 1,3-pentadiene, which adduct 1,2- or 1,4- will be formed as the predominant product is to be stated.
Concept introduction:
Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of bromide ion on each of these forms leads to the formation of a mixture of 1,2- and 1,4-addition products. The more stable form of the allyl cation will yield the major product.
To state:
Which adduct, 1,2- or 1,4-, will be formed as the predominant product during the addition of HCl to 1,3-pentadiene, by looking at the possible catrbocation intermediates in the reaction.
Trending nowThis is a popular solution!
Chapter 14 Solutions
Organic Chemistry
- In light of the fact that tertiary alkyl halides undergo spontaneous dissociation to yield a carbocation plus halide ion (see Problem 10-45), propose a mechanism for the following reaction.arrow_forwardBr Brz CH3 CH3 H3C CH2CI2 H3C Br Electrophilic addition of bromine, Br2; to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl). In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br: :Br: .CH3 H3C H3C CH3 Br:arrow_forward13:22 4G O The following scheme shown will lead to formation of which major product from benzene? HNO, Br Product H,So. FeCl, OAP-Bromonitrobenzene O B. Meta-Bromonitrobenzene OC Meta-Bromoaniline O D. None of the above options is correct Add a caption... > Status (Custom) +arrow_forward
- Please fill in the blanks!! Which set of reagents (given below) would produce the products given in the following reaction? A Br₂, hv F NBS K heat B Br₂, DCM G H₂, Pd Br ? с HBr, DCM H LDA L Grubb's D HBr, H₂O I KMnO4 M CH₂l₂, Zn E HBr, H₂O₂ 1. Li, 2. Cul Brarrow_forwardDevise a synthesis of (1Z,3E)-1-phenyl-1,3-octadiene from 1-hexyne and (Z)-2-bromostyrene using a Suzuki coupling. Br + -C C-H 1-hexyne (Z)-2-bromostyrene (12,3E)-1-phenyl-1,3-octadienearrow_forwardThis is a multistep syntheses. More than one reagent/reaction will be necessary to produce the product. Provide all necessary reaction conditions (HBr, HgSO4, etc.) and the products produced after each step of the synthesis.arrow_forward
- 8-) following reactions. Predict the major and minor products of the EtO CH;CH,CHCH, BuO, Brarrow_forwardPlease fill in the blanks!! Which set of reagents (given below) would produce the products given in the following reaction? A Br₂, hv F NBS K heat B Br₂, DCM G H₂, Pd C HBr, DCM H Br₂, H₂O L Grubb's D HBr, H₂O I KMnO4 M CH₂l₂, Zn E HBr, H₂O₂ J 1. Li, 2. Cularrow_forwardQuestion 11 Propose best Williamson ether syntheses for the following compounds. Select all applicable options (multiple answers can be possible). Note: Some compounds cannot be made using Williamson synthesis reaction. A: Хон OH ΚΗ مر OK Br SN2 KH B: OH OK SN1 C: Α ABC ☐ C 1000 Br Cannot be synthesized using Williamson ether syntheses.arrow_forward
- Please fill in the blanks!! Which set of reagents (given below) would produce the products given in the following reaction? OH OH ? A E В C D Br2, H20 Br2, DCM HBr, DCM HBr, H20 HBr, H2O2 G H I J F NBS H2, Pd 03, DMS KMNO4 1. Li, 2. Cul K L M heat Grubb's CH212, Znarrow_forward14-22 In light of your answer to Problem 14-21 propose mechanisms for the reactions below. (a) ÇO2CH3 .CO2CH3 Heat + CO2 + `CO2CH3 ČO2CH3 (b) CH3 CH3 N' N. Heat + C=CH + N2 N. N' CH3 CH3arrow_forwardHO NH2 CO₂Me PG! A NH HO PG² HO CO₂Me PG! NH `PG³ PG! `NH PG3 PG! `NH B PG2 CO₂Me C PG20 LiBH4 strong reducing agent, strong nucleophile PG! NH OHarrow_forward