Chemical Properties of Alcohol

Q.

Why the ease of dehydration of alcohols follows a sequence, tertiary $>$ secondary $>$primary?

Q.

The compound which will not give iodoform test on treatment with alkali and iodine is:

1. Isopropyl alcohol

2. Acetone

3. Diethyl ketone

4. Ethanol

Q. The reaction of t-butyl chloride and sodium ethoxide gives mainly

1. t-butyl ethyl ether
2. 2, 2-Dimethyl butane
3. 2-methylprop-1-ene
4. Isopropyl-n-propyl ether

Q.

What is the correct order of reactivity of alcohols in the following reaction?
$R-OH+HCl\stackrel{ZnC{l}_2}{\to }R-Cl+H_{2}O$
(a) $1^{\circ }>2^{\circ }>3^{\circ }$
(b) $1^{\circ }<2^{\circ }>3^{\circ }$
(c) $3^{\circ }>2^{\circ }>1^{\circ }$
(d) $3^{\circ }>1^{\circ }>2^{\circ }$

Q.

What is the major product formed by HI on reaction with

1. 
2. 
3. 
   
4. 

Q. Alkyl iodides are often prepared by the reaction of alkyl chlorides/ bromides with $NaI$ in dry acetone. This reaction is known as

1. Sandmayer's reaction
2. Finkelstein reaction
3. Markovnikov’s reaction
4. Swarts reaction

Q.

Which alcohol reacts faster with $\mathrm{HCl}/{\mathrm{ZnCl}}_2$ ?

Q.

Give a chemical test to distinguish between the following pair of compounds

1: n-propyl alcohol and isopropyl alcohol

2: methanol and ethanol

3: cyclohexanol and phenol

4: propan-2-ol and 2 methylpropan-2-ol

5: phenol and anisole

6: ethanol and diethyl Ether

Q. An alcohol $X\left(C_7{H}_{16}O\right)$ shows immediate turbidity with $HCl/ZnC{l}_2$ and can be resolved into enantiomers. Also, X has tertiary carbon. How many $C{H}_3$ - groups are present in X?

Q. In the presence of peroxide, $HCl$ and $HI$ do not give anti-Markownikoff's addition of alkenes because:

1. One of the step is endothermic in both $HCl$ and $HI$
2. Both $HCl$ and $HI$ are strong acids
3. $HCl$ is oxidising and $HI$ is reducing
4. All the steps are exothermic in case of $HCl$ and $HI$

Q. On nitration, the major product that chlorobenzene gives is:

1. 1-chloro-4-nitrobenzene
2. 1-chloro-3-nitrobenzene
3. 1, 4-dinitrobenzene
4. 2, 4, 6-trinitrobenzene

Q. Which among the following is Jones reagent?

1. $Cr{O}_{3}inaqueousacetone$
2. $Tert-amylalcohol$
3. $AlkalineKMn{O}_4$
4. $Conc.H_{2}S{O}_4$

Q.

Which one of the following has the lowest boiling point?

1. ${\mathrm{CH}}_3\mathrm{I}$

2. ${\mathrm{CH}}_3\mathrm{CI}$

3. ${\mathrm{C}}_2{\mathrm{H}}_5\mathrm{CI}$

4. ${\mathrm{C}}_2{\mathrm{H}}_5\mathrm{Br}$

Q. Among the following, which is the most reactive towards alcoholic KOH

1. $C{H}_{3}C{H}_{2}C{H}_{2}Br$
2. $C{H}_{3}COC{H}_{2}C{H}_{2}Br$
3. $C{H}_2=CHBr$
4. $C{H}_{3}C{H}_{2}Br$

Q.

Name the reagents used in the following reactions
Oxidation of a primary alcohol to carboxylic acid.

Oxidation of a primary alcohol to aldehyde

Bromination of phenol to 2, 4, 6 - tribromophenol

Benzyl alcohol to benzoic acid

Dehydration of propan-2-ol to propene

Butan-2-one to butan-2-ol

Q.

113. Alcohol can act as an acid as well as a base. Justify the statement.

Q. When ethylene glycol is heated with oxalic acid in the presence of conc. $H_{2}S{O}_4$, the product formed is:

1. 
2. 
3. 
4. 

Q. Arrange the following in increasing order of boiling point:
(i) $C{H}_3-C{H}_2-C{H}_2-C{H}_2-Br$
(ii) $(C{H}_3{)}_2-CH-C{H}_2-Br$
(iii) $(C{H}_3{)}_2-CH-Br$

1. $i>ii>iii$
2. $ii>i>iii$
3. $i>iii>ii$
4. $iii>ii>i$

Q. $C_2{H}_{5}Cl+AgF\to C_2{H}_{5}F+AgCl$
The above reactioin is called-

1. Finkelstein
2. Swartz
3. Stephen
4. Wurtz

Q. The reaction of toluene with chlorine in presence of ferric chloride gives predominantly :

1. benzoyl chloride
2. m-chlorotoluene
3. benzyl chloride
4. o- and p-chlorotoluene

Q. Reaction of Grignard reagent, $C_2{H}_{5}MgBr$ with $C_8{H}_{8}O$ followed by hydrolysis gives compound ''A'' which reacts instantly with Lucas reagent to give compound B, $C_{10}{H}_{13}Cl$.
Compound (B) is

1. 
2. 
3. 
4. 

Q. Which of the following compound shows instant turbidity with $HCl+ZnC{l}_2$?

1. Isopropyl alcohol
2. Ethyl alcohol
3. Benzyl alcohol
4. Neopentyl alcohol

Q. Write the structures of the main products in the following reactions :

Q. In which of the following conversions, phosphorus pentachloride is used as the reagent?

1. $C{H}_{3}C{H}_{2}OH\to C{H}_{3}C{H}_{2}Cl$
2. $H_{2}C=C{H}_2\to C{H}_{3}C{H}_{2}Cl$
3. $CH\equiv CH\to C{H}_2=CHCl$
4. None of the above

Q. How many of the following structure can undergo ring expansion ?
a)


b)

c)

1. 1
2. 4
3. \N
4. 2

Q. The major product in the following reaction is $Ph-Cl+B{r}_2\stackrel{\text{Anhydrous}FeB{r}_3}{\to }$ Product

1. o-bromochlorobenzene
2. p-bromochlorobenzene
3. m-bromochlorobenzene
4. 2, 4, 6-tribromochloro benzene

Q. Chlorobenzene can be prepared by reacting aniline with

1. Hydrochloric acid
2. Cuprous chloride
3. Chlorine in the presence of anhyd $AlC{l}_3$
4. Nitrous acid followed by heating with cuprous chloride

Q. Which one of the following cannot give friedel craft's reaction?

1. Toluene
2. Benzene
3. Benzoic acid
4. Benzaldehyde

Q.

Among the following, one which reacts most readily with ethanol is:

1. p-nitrobenzyl bromide

2. p-chlorobenzyl chloride

3. p-methoxybenzyl bromide

4. p-methoxybenzyl chloride

Q. Give the decreasing order of the reaction rates of the following benzyl alcohol with $HBr$.

1. $I>II>III>IV$
2. $IV>I>III>I$
3. $II>I>III>IV$
4. $IV>III>I>II$