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Complete the following and state the rel...

Complete the following and state the relations between configurations of the reactant and products.
(i) `._L-MeCH(OH)Et + HBr rarr` ?
(ii) `._L-MeCH(OAc)Et + 2 NaOH rarr` ?
(iii) `._L-MeEtPrCOMe + HI rarr` ?

Text Solution

Verified by Experts

(a) If no bond to the asymmetric `C` atom is broken, no inversion takes place.
(b) If it breaks, then for `SN^2` reaction inversion takes place , and for `SN^1`, reaction and racemisation take place.
(Sign for inversion `rArr rarr`)
(i) `SN^1`, retention, and racemisation

No change in configuration and hence retention.
(iii) `SN^2`, retention, and racemisation (`3^@` ether) :
.
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Knowledge Check

  • Consider the following sequence of reaction and identify the final product (Z). CH_3-CH=CH_2overset(HBr)rarr(X)overset(Aq.NaOH)rarr(Y)overset(NaOH+l_2)rarr(Z)

    A
    `CH_3CHICH_3`
    B
    `CH_3CH_2CH_2I`
    C
    `CHI_3`
    D
    `CH_3COCH_3`

  • Consider the following reactions PhBr underset(Et_(2)O,"heat")overset(Mg)rarr A The product (C ) is

    A
    `PhCHOHCH_(3)`
    B
    `PhCH_(2)CH_(2)OH`
    C
    `PhCH_(2)CHO`
    D
    `PhOCH_(2)CH_(3)`

  • Consider the following sequence of reactions PhBroverset(Mg)underset(Et_(2)O,heat)(rarr)A The major product formed (C ) is

    A
    `PhCH_(2)CHOHCH_(3)`
    B
    `PHCH_(2)COCH_(3)`
    C
    `Phoverset(CH_(3))(C )HCH_(2)OH`
    D
    `Phoverset(CH_(3))overset(|)(C )HCH_(2)OH`