Alcohols, Phenols and Ethers

Consider the following sequence of reactions [figure] The major product P is:

1. [figure]
2. [figure]
3. [figure]
4. [figure]

4.7 g of phenol is heated with Zn to give product X. If this reaction goes to 60% completion then the number of moles of compound X formed will be 10-2. (Nearest Integer) (Given molar mass in g mol-1 : H:1, C:12, O:16)

Consider the following reaction. [figure] In the light of the above statements, choose the correct answer from the options given below :

1. Both Statement I and Statement II are true
2. Both Statement I and Statement II are false
3. Statement I is true but Statement II is false
4. Statement I is false but Statement II is true

Consider compounds A, B and C with following structural formulae A = CH3-CH2-CH2-CH2-CH2-OH B = CH2=CH-CH2-CH2-CH3 C = HO-CH2-CH2-CH(OH)-CH3 For the conversion of B from A , reagent (D) required is and structural formula of product (E) obtained when C undergoes same reaction using excess reagent (D) is .

1. D: Conc. H2SO4; E: CH2=CH-CH(OH)CH3
2. D: PCC; E: HO-CH2-CH2-CH=CH2
3. D: PCC; E: CH2=CH-CH=CH2
4. D: Conc. H2SO4 or H3PO4; E: CH2=CH-CH=CH2

One mole of phenol is treated with dilute HNO3 at 298 K to give a mixture of products. The mixture is separated by steam distillation. The steam volatile compound (X) is separated. The increase in percentage of oxygen in (X) with respect to phenol is 10-1% (Given molar mass in g mol-1 H : 1, C : 12, N : 14, O : 16)

Amongst the following, the total number of compounds soluble in aqueous NaOH at room temperature is: [figure]

1. 5
2. 4
3. 6
4. 3

Consider the following reaction sequence : [figure] Compound (y) develops characteristic colour with neutral FeCl3 solution. Identify the INCORRECT statement from the following for the above sequence.

1. Compound y will dissolve in NaHCO3 and evolve a gas.
2. Compound x is more acidic than compound y.
3. Both compounds x and y will dissolve in NaOH.
4. Both compounds x and y will burn with sooty flame.

Consider the following two reactions A and B. [figure] Numerical value of [molar mass of x + molar mass of y] is

1. 46
2. 160
3. 88
4. 4

A hydroxy compound (X) with molar mass 122 g mol-1 is acetylated with acetic anhydride, using a large excess of the reagent ensuring complete acetylation of all hydroxyl groups. The product obtained has a molar mass of 290 g mol-1. The number of hydroxyl groups present in compound (X) is:

1. 2
2. 4
3. 3
4. 5

From the following, how many compounds contain at least one secondary alcohol? [figure] Choose the correct answer from the options given below :

1. Three
2. Two
3. Four
4. Five

A mixed ether (P), when heated with excess of hot concentrated hydrogen iodide produces two different alkyl iodides which when treated with aq. NaOH give compounds (Q) and (R). Both (Q) and (R) give yellow precipitate with NaOI. Identify the mixed ether (P) :

1. [figure]
2. [figure]
3. [figure]
4. [figure]

Given below are two statements : In the light of the above statements, choose the correct answer from the options given below

1. Statement I is true but Statement II is false
2. Both Statement I and Statement II are true
3. Both Statement I and Statement II are false
4. Statement I is false but Statement II is true

3,3-Dimethyl-2-butanol cannot be prepared by : Choose the correct answer from the options given below :

1. B and E Only
2. B, C and E Only
3. B and C Only
4. B Only

Which one of the following reactions will not lead to the desired ether formation in major proportion? (iso-Bu isobutyl, sec-Bu sec-butyl, n-Pr n-propyl, tBu tert-butyl, Et ethyl)

1. [figure]
2. iso-Bu O Na + sec-BuBr sec-Bu–O–iso-Bu
3. [figure]
4. tBu O Na + EtBr tBu-O-Et

Given below are two statements : In the light of given statements, choose the correct answer from the options given below

1. Statement I is false but Statement II is true
2. Statement I is true but Statement II is false
3. Both Statement I and Statement II are true
4. Both Statement I and Statement II are false

Benzene is treated with oleum to produce compound (X) which when further heated with molten sodium hydroxide followed by acidification produces compound (Y). The compound Y is treated with zinc metal to produce compound (Z). Identify the structure of compound (Z) from the following options.

1. [figure]
2. [figure]
3. [figure]
4. [figure]

An organic compound (X) with molecular formula C3H6O is not readily oxidised. On reduction it gives C3H8O (Y) which reacts with HBr to give a bromide (Z) which is converted to Grignard reagent. This Grignard reagent on reaction with (X) followed by hydrolysis gives 2,3-dimethylbutan-2-ol. Compounds (X), (Y) and (Z) respectively are:

1. CH3CH2CHO, CH3CH2CH2OH, CH3CH2CH2Br
2. CH3COCH3, CH3CH(OH)CH3, CH3CH(Br)CH3
3. CH3COCH3, CH3CH2CH2OH, CH3CH(Br)CH3
4. CH3CH2CHO, CH3CH=CH2, CH3CH(Br)CH3

A toxic compound "A" when reacted with NaCN in aqueous acidic medium yields an edible cooking component and food preservative "B". "B" is converted to "C" by diborane and can be used as an additive to petrol to reduce emission. "C" upon reaction with oleum at 140 C yields an inhalable anesthetic "D". Identify "A", "B", "C" & "D", respectively :

1. Methanol; acetic acid; ethanol; diethyl ether
2. Ethanol; acetonitrile; ethylamine; ethylene
3. Methanol; formaldehyde; methyl chloride; chloroform
4. Acetaldehyde; 2-hydroxypropanoic acid; propanoic acid; dipropyl ether

Which one of the following, with HBr will give a phenol?

1. [figure]
2. [figure]
3. [figure]
4. [figure]

Given below are two statements : In the light of the above statements, choose the correct answer from the options given below :

1. Statement I is false but Statement II is true
2. Both Statement I and Statement II are true
3. Statement I is true but Statement II is false
4. Both Statement I and Statement II are false

Identify the products [A] and [B], respectively in the following reaction: [figure]

1. [figure]
2. [figure]
3. [figure]
4. [figure]