Question

1. Draw the line structures and arrange the following substrates in order of increasing SN2 reactivity with NaCN: Bromoethane, 1-chloro-3,3-dimethylpentane, 1-chloro-2,2-dimethylpentane, and 2-bromo-2- methylpentane. (1 pt) 2. Design a synthetic route for the following conversion of methylcylohexane into compound A using retrosynthesis analysis. You may use any other reagents that you need. (1 pt) 3. Predict which of the following two compounds will undergo an E2 reaction more rapidly in presence of EtONa/EtOH. Draw the reaction product(s) and the mechanism for the faster reaction using the correct chair conformation for the substrate (starting material). (1 pt) 4. Identify and draw the mechanism involved in each of the following two reactions in order to explain the product formed. (1 pt) M . Bere

Answer 1

In SN2 Rathway backside attack on the Electrophile by nucleophile. So les hindered Alkanes react quite fastly lie they are more reactive towards SN2) by SN? mechanism. CH₃ CH₂ Br Bromo ethane CH₂ CH₂ CH₂ - ( - Cty Che. 1- chloro-3, 3-dimethyl pentine (Hz CH₂ CH₂ - CH₂ - (- Chell f-chloro-2,2-dimethyl pentane علاج سرط) - وط) حوط) Hy Zecarbon 2- bromo-2-methylpentane Bromo ethane is the simplest of them all with no stev hindrance & Brono ethane reacts fastest 2- bromo-2-methylpentane contains 3° carbon atom on which leaving group (- Berd is attached. Here storic hindrance for coming nucleophile (N) į more than any of the others. So, it reacts . most

Out of 1-chloro-3,3-dimethyl pentane and 1 chloro-2, 2- dimethyl pentane , both of them contains primary Carbon on which leaving group is cettaned but steric hindrance is more near to the Electrophides centre (carson of (Hg (1) i I-chloro-g, 2-dimethyl pentane do it reacts slowly than 1-chloro-3, 3-dimethylpentane & Increasing order of SN2 reactivity is a 2-610 mo-4 methylpentane<1-chl06-22-dimethylpentane {t-chloro- 3,3-dimethyl pentane a Promoethane
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