$HOOC-COOH + HO^{18}CH_2-CH_2^{18}OH \xrightarrow[H^+]{\Delta} (A)$; Product $(A)$ is:

  • A
    Cyclic ester with oxygen atoms from the acid
  • B
    Cyclic ester with $^{18}O$ atoms from the alcohol in the ring
  • C
    Cyclic ester with $^{18}O$ atoms in the carbonyl group
  • D
    Linear monoester

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Match the reaction in Column-$I$ with the mechanism in Column-$II$.
Column-$I$ (Reaction)Column-$II$ (Mechanism)
$A$. $CH_3OCH_2CH_3 + HI \to CH_3I + CH_3CH_2OH$$i$. $S_{E}2$ Aromatic
$B$. $(CH_3)_3COCH_3 + HI \to CH_3OH + (CH_3)_3CI$$ii$. $S_{N}1$
$C$. $C_6H_5OCH_3 + Br_2(CH_3COOH) \to p$-Bromoanisole$iii$. Elimination $(\beta)$
$D$. $CH_3CH_2OH + H_2SO_4 (443 \ K) \to CH_2=CH_2$$iv$. $S_{N}2$

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Arrange the following sets of compounds in order of their increasing boiling points:
$(a)$ Pentan$-1-$ol,butan$-1-$ol,butan$-2-$ol,ethanol,propan$-1-$ol,methanol.
$(b)$ Pentan$-1-$ol,$n-$butane,pentanal,ethoxyethane.

Match the following column:
Column-$I$ (Reaction) Column-$II$ (Electrophile)
$A$. $C_6H_6 + CH_3Cl \xrightarrow{AlCl_3} C_6H_5CH_3$ $P$. $CO_2$
$B$. $C_6H_5OH + CO_2 \xrightarrow[H^+]{NaOH} \text{Salicylic acid}$ $Q$. $:CCl_2$
$C$. $C_6H_5OH + CHCl_3 \xrightarrow{KOH} \text{Salicylaldehyde}$ $R$. $\stackrel{+}{C}H_3$
$D$. $C_6H_6 + SO_3 \xrightarrow{H_2SO_4} C_6H_5SO_3H$ $S$. $\stackrel{+}{S}O_3H$
$T$. $SO_3$

Match the columns:
Column-$I$Column-$II$
$A$. Methanol$p$. Conversion of phenol to salicylic acid
$B$. Kolbe's reaction$q$. Wood spirit
$C$. Williamson's reaction$r$. Vapours are passed over heated copper at $573 \ K$
$D$. Conversion of $2^\circ$ alcohol to ketone$s$. Reaction of alkyl halide with sodium alkoxide

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Consider the following methods $:$
$I$: Hydration of olefins
$II$: Hydrolysis of alkyl halide
$III$: Reduction of carbonyl compounds
Which of these can be used to prepare alcohols ?

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