How many of the following responses are true? 1. A primary alkyl halide will tend to...

How many of the following responses are true?

1. A primary alkyl halide will tend to react through an SN2 mechanism because there is little hindrance to backside attack and a primary carbocation is not very stable
2. 3-bromo-3-methylpentane will undergo substitution through an SN2 mechanism
3. If R-2-bromopentane is allowed to react with OH- the product will be S-2-pentanol
4. SN1 leads to a racemization of sterechemistry due to the nucleophile attacking from the backside and the leaving group leaving
5. SN2 leads to a racemization of sterechemistry due to the nucleophile attacking from the backside and the leaving group leaving

I thought 1, 3, and 4 were right, but my answer was wrong! Please help!

Expert Solution

1. A primary alkyl halide will tend to react through an SN2 mechanism because there is little hindrance to backside attack and a primary carbocation is not very stable (True)
2. 3-bromo-3-methylpentane will undergo substitution through an SN2 mechanism. (False, it is a tertiary halide, it will preffer SN1 reaction as it will form stable carbocation intermediate).
3. If R-2-bromopentane is allowed to react with OH- the product will be S-2-pentanol. (True, through SN2 reaction)
4. SN1 leads to a racemization of sterechemistry due to the nucleophile attacking from the backside and the leaving group leaving. (False, in SN1 reaction, a plainer carbocation intermediate is formed due to sp2 hybridization of positively charged carbon and this allow the attack of nucleophile either from top or bottom of plaine carbocation which causes the racenization).
5. SN2 leads to a racemization of sterechemistry due to the nucleophile attacking from the backside and the leaving group leaving. (False, SN2 causes inversion of configuration called as Walden inversion not racemization).

queen_honey_blossom answered 1 year ago

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