Question

Substitution Problems I. In each of the problems below, label the alkyl halide as primary, secondary, or tertiary. Label the nucleophile as strong or weak. Decide whether an SN2 or an Sy1 reaction occurs. After, show the mechanism and product or products. Indicate stereochemistry where appropriate. a. Reaction of 1-bromopropane and sodium methoxide in methanol CH3 Na CH,Oн Br b. Reaction of 2-bromopropane in ethanol CH3CH2OH Br c. Reaction of (R) 3-chloro-3-methyl heptane in acetic acid Ci Cн CH,COOH но d. Reaction of the molecule shown with sodium methoxide in aprotic solvent CH3 oO.. Na CH3 acetone Br

Answer 1

SN2 Transition State OCH₃7 Nao-chz Chow IV-By J strong muceophile |_ NaBr - ů Br + inalkyl halide CH₂OH V oreiz The above reaction alkyl kalite r i-alkylkalide The nucleophile is strong nuclophile This is sxl2 reaction. There is no strochemistry because it is substituted on terminal position. But SND reaction the stereochemistry í inversion. stercochemistry - by Reaction of 2-bromopropane in ethanol - Yor + CH₃CHO SNA, yah ets of Hby 2-alkyl halide weare nucleophile The above reaction the alkyl halide i d-alkyl kalede - The nulophile ù weare nulophile The reaction i i sN1 reaction storochemistry ů recimie mixture [501150%) because carbocation informdate having planas geometry Stage year are yo step-21 Letretroit has o chretroit -HBK

- a Reaction of (R) 3-chloro-3-methel hugtame in aetic old С +HO CH₂ SNA - wt 3-alkyl halide CH₂COOH wears nucleophile ✓ + HCL Mechanism? stop-1} - We + c Stop-2 - / WI Veren er + Hör CH₂ V sro والا hero t HU Alkyl halide is 30-alkyl holide Nectophile is weare nuloph't The reaction is SN 1 reaction product is recimic mixture

CH₂ SN2 Y H + Nao CH₂ - Acetoni - rill & -alkyl halice CH₃ SN2 Locha - CH₂ H + Na O-CH, Acetone By Inversion Storochenishow off zlos o alkyl halide Mechanisms- CH3 String ö- H + NaCH₃ -CH₃ l acctoni L CH3 Alkyl halide in d e H Inversion storochemistry Nucleophile is strong nedophile The reaction is sna stewchemistry is inversion stone Stenochemistry tel