Interpretation:
It is to be identified that the compound in each of the given pair reacts at a faster rate in an
Concept introduction:
The nucleophilic substitution reaction of methyl and primary
The nucleophilic substitution reaction of secondary and tertiary alkyl halide proceeds through
The
The
The formation of carbocation is the rate determining step in
The nucleophileattacks on the electrophilic carbon from opposite side of leaving group (i.e. backside attack) in
The nucleophilecan attacks from either face of planar carbocation in
The order of rate of alkyl halide toward substitution by nucleophiles on the basis of better leaving group is
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Organic Chemistry - Standalone book
- The reaction of methylpropene with HBr in ether gives one of the two products below as the major product. Br HBr Br ether Product A Product B Product would have a higher energy transition state for the formation of the intermediate leading to it. O A O B O Both products would have the same transition state.arrow_forwardThe reaction of 1-bromobutane with which of the following nucleophiles is a carbon chain-lengthening reaction? sodium acetylide (NaC=CH) sodium hydroxide (NaOH) O ammonia (NH3) potassium iodide (KI)arrow_forwardWrite out the mechanism (intermediate/transition state) for this reaction; Br CH3 NaOCH₂ E₂arrow_forward
- Which of the following reagents is best to achieve the given transformation? H3C, C CH3OH C N2OH C TSCI, Py C KOtBuarrow_forwardWhat is the product of the reaction of ethyl bromide with each of the following nucleophiles? CH3CH2CH2O- CH3C≡C- (CH3)3Narrow_forwardAnswer the question below the reaction. OH tom ta + H₂O In the second step of the reaction mechanism, which of the following is formed? H3C H3C H3C H3C + Excess NH4C1 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 H₂SO4arrow_forward
- The expected major product from the treatment of 1-pentyne with 1 equivalent of HBr is: 1,2-dibromopentane 1-bromo-1-pentene 2-bromo-1-pentene 1,1-dibromopentane 2,2-dibromopentanearrow_forwardIn hydrobromination of 3-hexene, which of the following pairs of species act as nucleophiles? 3-hexene, Br– 3-hexene, HBr HBr, Br– HBr, Br2arrow_forwardWhat is the product of the following sequence of reactions? Сно NaCN H,Ot, heat HCI OH OH CO2H CN Co,H CN OH OH II II IVarrow_forward
- Treatment of 1,3-dichloropropane with potassium cyanide results in the formation of pentanedinitrile. The rate of this reaction is about 1000 times greater in DMSO than in ethanol. Account for this difference in rate. CI + 2 KCN NC + 2 KCI CN 1,3-Dichloropropane Pentanedinitrilearrow_forwardDraw the most stable resonance form for the intermediate in the following electrophilic substitution reaction. OCH3 CH3CI / AICI 3 H3C OCH 3arrow_forwardThe following nucleophilic substitution reaction has been reported in the chemical literature. Using what you know about nucleophilic substitution in simple systems, predict the major product of the reaction. NE Cl H₂O HO Click and drag to start drawing a structure. 0 D 0arrow_forward