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Q.Write IUPAC name of the following compounds:

(i) CH3−CH(CH3)−CH(OH)−C(CH3)2−CH3CH_3-CH(CH_3)-CH(OH)-C(CH_3)_2-CH_3
(ii) HO−CH2−CH(OH)−CH2OHHO-CH_2-CH(OH)-CH_2OH
(iii) H3C−CH2−O−CH(CH3)−CH2−CH3H_3C-CH_2-O-CH(CH_3)-CH_2-CH_3
(iv) 2,6-dimethylphenol (a benzene ring bearing an −OH-OH group with a −CH3-CH_3 group at each of the two ortho positions)
(v) H3C−CH(Cl)−CH(CH3)−CH(CH3)−CH2OHH_3C-CH(Cl)-CH(CH_3)-CH(CH_3)-CH_2OH OR Predict the products obtained in the following reactions:
(i) C6H5−OC2H5C_6H_5-OC_2H_5 (ethoxybenzene) +HBr⟶+ HBr \longrightarrow
(ii) C6H5−OC2H5C_6H_5-OC_2H_5 (ethoxybenzene) →conc. H2SO4/conc. HNO3\xrightarrow{\text{conc. } H_2SO_4 / \text{conc. } HNO_3}
(iii) H3C−CH=CH2→H2O/H+H_3C-CH=CH_2 \xrightarrow{H_2O/H^+}
(iv) H3C−CH2−CH(CH3)−CHO→NaBH4H_3C-CH_2-CH(CH_3)-CHO \xrightarrow{NaBH_4}
(v) benzene-1,2-dicarboxylic acid, o-C6H4(COOH)2o\text{-}C_6H_4(COOH)_2 →SOCl2, Temp.\xrightarrow{SOCl_2,\ \text{Temp.}}
Uttar Pradesh UpmspUP Board (UPMSP) Intermediate 2024Subjective· 5mImportance★★★★★
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Number each parent chain to give the –OH (or –ol) the lowest locant, name substituents alphabetically: (i) 2,2,4-trimethylpentan-3-ol, (ii) propane-1,2,3-triol, (iii) 2-ethoxybutane, (iv) 2,6-dimethylphenol, (v) 4-chloro-2,3-dimethylpentan-1-ol.

(i) CH3−CH(CH3)−CH(OH)−C(CH3)2−CH3CH_3{-}CH(CH_3){-}CH(OH){-}C(CH_3)_2{-}CH_3. Longest chain through the –OH carbon is 5 C (pentan-3-ol). Numbering to give –OH the lowest locant places two methyls at C2 and one at C4:

⇒2,2,4-trimethylpentan-3-ol\Rightarrow \textbf{2,2,4-trimethylpentan-3-ol}

(ii) HO−CH2−CH(OH)−CH2OHHO{-}CH_2{-}CH(OH){-}CH_2OH. A 3-carbon chain with –OH on all three carbons (glycerol):

⇒propane-1,2,3-triol\Rightarrow \textbf{propane-1,2,3-triol}

(iii) H3C−CH2−O−CH(CH3)−CH2−CH3H_3C{-}CH_2{-}O{-}CH(CH_3){-}CH_2{-}CH_3. This is an ether: the larger group is the butan-2-yl chain, the smaller is ethoxy at C2:

⇒2-ethoxybutane\Rightarrow \textbf{2-ethoxybutane}

(iv) A benzene ring with –OH and a –CH3_3 at each ortho (2 and 6) position:

⇒2,6-dimethylphenol\Rightarrow \textbf{2,6-dimethylphenol}

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