Alcohols, Phenols, and Ethers - Class 12

3,3-dimethylbut-1-ene is treated with excess $D_2O$ in the presence of a catalytic amount of $D_2SO_4$ at 298 K to yield a major product $P$. Assuming the reaction proceeds via the most stable carbocation intermediate and no reversible alkene formation occurs, determine the number of hyperconjugable $\alpha$-hydrogens (excluding $\alpha$-deuterium) in the most stable carbocation intermediate, and the number of chiral centers in $P$.

Consider the following reaction sequence:

$\text{6-methylhept-5-en-2-one} \xrightarrow{\text{1. } \ce{NaBH4}, \text{ EtOH}, 298\text{ K}} \text{Intermediate A}$

$\text{Intermediate A} \xrightarrow{\text{2. } \ce{H2SO4} \text{ (aq, } 10\%), 298\text{ K}} \text{Major Product B}$

Identify the structure of the Major Product B.

Consider the acid-catalyzed hydration of an optically pure sample of (3S)-3-methylhex-1-ene using dilute $\ce{H2SO4}$ at 298 K. Considering only the alcohol products formed, let $x$ be the total number of fractions obtained upon careful fractional distillation of the product mixture. Let $y$ be the number of these fractions that are optically active. What is the value of $x \times y$?

Consider the acid-catalyzed hydration of 2-(1,1-dimethylethyl)-3,3-dimethylbut-1-ene using dilute aqueous $\ce{H2SO4}$ at 298 K. The reaction yields a major product $P$. Which of the following represents the correct IUPAC name of $P$ and the primary kinetic/thermodynamic driving force for its formation?

An unknown alkene $X$ ($C_6H_{12}$) undergoes reductive ozonolysis to yield formaldehyde and 2,2-dimethylpropanal. When $X$ is subjected to acid-catalyzed hydration using dilute $H_2SO_4$ at 298 K, it forms compound $P$ as the major product. Conversely, when $X$ is treated with $BH_3 \cdot THF$ followed by oxidation with alkaline $H_2O_2$, it yields compound $Q$ as the major product. Identify the correct IUPAC names for $P$ and $Q$.

Consider the enantiomerically pure compound \textbf{X}, $(R)$-5-bromo-4-methylpent-1-ene. Compound \textbf{X} is subjected to the following reaction sequence:

1. $\ce{BH3 \cdot THF}$, followed by $\ce{H2O2 / NaOH (aq)}$
2. $\ce{Mg}$ turnings, dry ether
3. $\ce{CO2 (s)}$, followed by acidic workup ($\ce{H3O+}$)

Identify the major organic product \textbf{Y} and its stereochemical nature.

Consider the organic substrate 6-hepten-2-one. It is subjected to two independent reaction sequences to yield major products $\textbf{X}$ and $\textbf{Y}$.

Sequence I: $\ce{6-hepten-2-one ->[1. LiAlH_4 (excess), Et_2O][2. H_3O^+] \textbf{X}}$

Sequence II: $\ce{6-hepten-2-one ->[1. BH_3 \cdot THF (excess)][2. H_2O_2, NaOH, H_2O] \textbf{Y}}$

Which of the following correctly identifies the structures of the major products $\textbf{X}$ and $\textbf{Y}$?

1-Methylcyclohex-1-ene is treated with $BD_3 \cdot THF$ followed by oxidation with $H_2O_2 / NaOH$ at $298\text{ K}$. Which of the following accurately describes the major product formed?

Consider the following reaction sequence starting from 2-methylbut-2-ene (Compound $\textbf{A}$):

$\textbf{A} \xrightarrow[\text{2. } \ce{H2O2, NaOH}]{\text{1. } \ce{BH3 \cdot THF}} \textbf{B} \xrightarrow{\ce{TsCl, Pyridine}} \textbf{C}$

Compound $\textbf{C}$ is subjected to elimination under two different conditions: Condition I: $\ce{t-BuOK / t-BuOH}, \Delta \rightarrow \textbf{D} \text{ (Major)}$ Condition II: $\ce{EtONa / EtOH}, \Delta \rightarrow \textbf{E} \text{ (Major)}$

Identify the major products $\textbf{D}$ and $\textbf{E}$.

Consider the following reaction sequence: $\ce{CH3-C(CH3)2-CH=CH2 \xrightarrow[(ii) NaBH4, OH^-]{(i) Hg(OAc)2, H2O/THF} P}$ $\ce{P \xrightarrow{POCl3, pyridine, 0^\circ C} Q (Major)}$ $\ce{Q \xrightarrow[(ii) Zn, H2O]{(i) O3, CH2Cl2, 195 K} R + S}$ Identify the major products R and S.

An alkene $\textbf{X}$ is synthesized by the Wittig reaction of 1-methylcyclopentane-1-carbaldehyde with methylenetriphenylphosphorane. $\textbf{X}$ is then subjected to three distinct hydration protocols to yield major products $\textbf{P}$, $\textbf{Q}$, and $\textbf{R}$:

$\textbf{Path A:}$ $\ce{H2O / H2SO4}$ (cat.), $\Delta \rightarrow \textbf{P}$

$\textbf{Path B:}$ (i) $\ce{Hg(OAc)2, H2O, THF}$ (ii) $\ce{NaBH4, NaOH} \rightarrow \textbf{Q}$

$\textbf{Path C:}$ (i) $\ce{BH3 \cdot THF}$ (ii) $\ce{H2O2, NaOH} \rightarrow \textbf{R}$

Identify the correct IUPAC names for the major products $\textbf{P}$, $\textbf{Q}$, and $\textbf{R}$.

1,2-Dimethylcyclopentene is subjected to oxymercuration using $\ce{Hg(OAc)2}$ in an aqueous medium at 298 K to form an organomercurial intermediate $X$ (prior to demercuration). Which of the following statements correctly describes the relative stereochemistry of the substituents in the major product $X$?

An alkene, \ce{3,3-dimethyl-1-butene}, is subjected to an alkoxymercuration-demercuration sequence. It is first reacted with \ce{Hg(OAc)2} in excess \ce{CH3OD}. The resulting organomercury intermediate is subsequently reduced using \ce{NaBD4} in aqueous \ce{NaOH}. Which of the following represents the major organic product formed?

Consider the reaction of 2-hydroxy-5-methyl-1-phenylhex-5-en-1-one with mercuric acetate in aqueous THF, followed by reduction with sodium borohydride in aqueous sodium hydroxide at $0^\circ\text{C}$.

$\text{2-hydroxy-5-methyl-1-phenylhex-5-en-1-one} \xrightarrow[2. \ce{NaBH4}, \ce{NaOH(aq)}, 0^\circ\text{C}]{1. \ce{Hg(OAc)2}, \ce{H2O/THF}} \text{Major Product (P)}$

Identify the major product (P).

Consider the isomeric substrates 1-fluoro-2-nitrobenzene ($\textbf{I}$) and 1-fluoro-4-nitrobenzene ($\textbf{II}$).\n\n\textbf{Reaction A:} $\textbf{I}$ and $\textbf{II}$ undergo $S_NAr$ with \ce{NaOCH3} in \ce{CH3OH} at 298 K with second-order rate constants $k_{ortho}$ and $k_{para}$, respectively.\n\n\textbf{Reaction B:} $\textbf{I}$ and $\textbf{II}$ are hydrolyzed using aqueous \ce{NaOH} at 400 K, followed by acidification, yielding phenols $\textbf{P}$ and $\textbf{Q}$, respectively, with acid dissociation constants $K_{a,ortho}$ and $K_{a,para}$ in water at 298 K.\n\nGiven that the Mesomeric ($-M$) effect of the \ce{-NO2} group is approximately equal at the ortho and para positions, select the correct relationship between the kinetic and thermodynamic parameters along with the primary governing factors.

Consider 2,6-di-tert-butylphenol ($\textbf{X}$) and phenol ($\textbf{Y}$) at $298\text{ K}$. Which of the following statements correctly identifies the thermodynamic and kinetic behavior of $\textbf{X}$ compared to $\textbf{Y}$, along with the correct underlying mechanistic rationale?

Consider the following aromatic carboxylic acids (typical products of Kolbe-Schmitt type reactions): I. \ce{2-Hydroxybenzoic acid} II. \ce{2,4-Dihydroxybenzoic acid} III. \ce{2,4,6-Trihydroxybenzoic acid} IV. \ce{2,6-Dihydroxybenzoic acid} V. \ce{3-Hydroxybenzoic acid}

These acids undergo acid-catalyzed decarboxylation via an $S_E2$ mechanism (electrophilic attack of $H^+$ at the ipso-carbon). Let $N$ be the rank of \ce{2,4-Dihydroxybenzoic acid} when the above acids are arranged in decreasing order of their decarboxylation rate (i.e., Rank 1 = fastest). Let $M$ be the total number of oxygen atoms in the most reactive acid among the given list. Let $P$ be the number of $\pi$ electrons delocalized in the arenium ion (Wheland intermediate) formed during the rate-determining step of this decarboxylation. Calculate the value of $(N \times P) + M$.

Consider the acid dissociation of $o$-nitrophenol (I) and $p$-nitrophenol (II) at $298\text{ K}$. Let $K_a(\text{I})$ and $K_a(\text{II})$ represent their respective acid dissociation constants. Which of the following correctly identifies the relative acidity order in water (polar protic solvent) versus benzene (non-polar aprotic solvent)?

Consider the azo coupling reactions of 3-aminophenol ($\textbf{X}$) with benzenediazonium chloride under two different pH conditions at $273 - 278\text{ K}$:

Reaction I: $\textbf{X} + \ce{PhN2+Cl-} \xrightarrow{\text{pH } 9-10} \textbf{P}$ (Major Product)

Reaction II: $\textbf{X} + \ce{PhN2+Cl-} \xrightarrow{\text{pH } 4-5} \textbf{Q}$ (Major Product)

Identify the correct IUPAC names for the major products $\textbf{P}$ and $\textbf{Q}$.

Consider the following reaction sequence:

$\ce{2-Nitrophenol ->[Br_2 (1 \text{ eq}), CS_2][273 \text{ K}] P (Major)}$ $\ce{P ->[\text{conc. } HNO_3, \text{ conc. } H_2SO_4][333 \text{ K}] Q (Major)}$ $\ce{Q ->[PCl_5][\Delta] R (Major)}$ $\ce{R ->[NaSCH_3 (1 \text{ eq})][\text{DMF, 298 K}] S (Major)}$

Identify the major product \textbf{S}.

Consider the bifunctional aromatic compound 4-(4-aminobenzyl)phenol. It is subjected to two separate electrophilic aromatic substitution reactions:

Reaction 1: Treatment with 1 equivalent of $Br_2$ in $CH_3COOH$ at 298 K yields major product P.

Reaction 2: Treatment with 1 equivalent of conc. $HNO_3$ and conc. $H_2SO_4$ at 288 K, followed by mild basic neutralization, yields major product Q.

Identify the major products P and Q.

Consider the following reaction sequence starting from 2,6-dimethylphenol: $\text{2,6-Dimethylphenol} \xrightarrow[\text{298 K}]{\ce{CrO2Cl2} \text{ (2 eq), } \ce{CS2}} \mathbf{A}$ $\mathbf{A} \xrightarrow{\ce{NaBH4}, \text{ EtOH}} \mathbf{B}$ $\mathbf{B} \xrightarrow{\ce{NaH} \text{ (excess), } \ce{CH3I} \text{ (excess), THF}} \mathbf{C}$ $\mathbf{C} \xrightarrow[\text{h}\nu]{\ce{NBS} \text{ (1 eq), } \ce{CCl4}} \mathbf{D} \text{ (Major Product)}$ Identify the correct IUPAC name of the final major product $\mathbf{D}$.

Consider the following reaction sequence starting from 4-hydroxybenzoic acid: \begin{enumerate} \item \ce{NaHCO3} (1 eq), \ce{CH3I} (1 eq), DMF, 298 K $\rightarrow$ \textbf{P} \item (i) \ce{NaH} (1 eq), THF, 298 K; (ii) \ce{(CH3)3C-Br}, 350 K; (iii) \ce{H3O+} workup $\rightarrow$ \textbf{Q} (Major organic product) \item Dilute \ce{HNO3}, 298 K $\rightarrow$ \textbf{R} (Major product) \end{enumerate} Identify the correct IUPAC name for the final major product \textbf{R}.

Consider the following two independent reaction sequences:

\textbf{Sequence 1:} 3-Methoxyphenol is treated with aqueous \ce{NaOH}. The mixture is evaporated to dryness, and the resulting solid is heated at $125^\circ\mathrm{C}$ under $5\text{ atm}$ of \ce{CO2} gas. Subsequent acidification with dilute \ce{HCl} yields \textbf{X} as the major product.

\textbf{Sequence 2:} 4-Nitrophenol is treated with aqueous \ce{NaOH}. The mixture is evaporated to dryness, and the resulting solid is heated at $125^\circ\mathrm{C}$ under $5\text{ atm}$ of \ce{CO2} gas. Subsequent acidification with dilute \ce{HCl} yields \textbf{Y} as the major product.

Identify the major products \textbf{X} and \textbf{Y}.

Consider the organic compound \textbf{P}, 3-\textit{tert}-butyl-5-methoxyphenol. \textbf{P} undergoes the following reaction sequence:\ 1. \ce{NaOH} (aq), followed by evaporation to dryness.\ 2. \ce{CO2} (g) at $125^\circ\text{C}$ and $5\text{ atm}$ pressure.\ 3. Dilute \ce{H3O+}, yielding major product \textbf{X}.\ 4. \textbf{X} is treated with \ce{(CH3CO)2O} in the presence of catalytic \ce{H2SO4} to yield major product \textbf{Y}.\ Identify the IUPAC name of product \textbf{Y}.

Sodium phenoxide is treated with \ce{CO2} at 400 K and 4-7 atm pressure, followed by acid hydrolysis to yield the major product $P$. Consider the following compounds: (I) Product $P$ (II) 3-Hydroxybenzoic acid (III) 4-Hydroxybenzoic acid (IV) Benzoic acid Identify the correct decreasing order of their acid dissociation constants ($K_a$) in aqueous medium at 298 K.

Consider the following reaction sequence starting from Phenol ($\ce{P}$):

$\ce{P ->[ (i) NaOH, CO2, 400 K, 5 atm ][ (ii) H3O^+ ] Q (Major)}$

$\ce{Q + CH3OH (excess) ->[ H2SO4 (cat.) ][ \Delta ] R}$

Let $v_R$ be the initial rate of formation of $\ce{R}$. An isomer of $\ce{Q}$, 4-hydroxybenzoic acid ($\ce{S}$), is subjected to identical Fischer esterification conditions to form product $\ce{T}$ with an initial rate $v_T$. Which of the following correctly compares $v_R$ and $v_T$, and identifies the primary mechanistic rationale?

Consider the following reaction sequences starting from phenol:

Reaction I: Phenol $\xrightarrow[125^\circ\text{C, 5 atm}]{\text{1. } NaOH, CO_2} \xrightarrow{\text{2. } H_3O^+} \mathbf{P}$ (Major Product)

Reaction II: Phenol $\xrightarrow[150^\circ\text{C, 5 atm}]{\text{1. } KOH, CO_2} \xrightarrow{\text{2. } H_3O^+} \mathbf{Q}$ (Major Product)

Let $c$ and $d$ be the position numbers of the carbon atoms attached to the $-COOH$ group in the aromatic rings of $\mathbf{P}$ and $\mathbf{Q}$ respectively, strictly assigning the carbon attached to the $-OH$ group as position 1.

When $\mathbf{P}$ and $\mathbf{Q}$ are treated separately with excess aqueous bromine ($Br_2/H_2O$), they undergo electrophilic aromatic substitution to form products $\mathbf{X}$ and $\mathbf{Y}$ respectively. Let $a$ and $b$ be the total number of bromine atoms present in one molecule of $\mathbf{X}$ and $\mathbf{Y}$ respectively.

Calculate the value of the expression: $(c \times d) + (a \times b)$.

Consider four phenolic compounds: Phenol (I), 4-Chlorophenol (II), 4-Methylphenol (III), and 4-Nitrophenol (IV). These compounds are subjected to the Reimer-Tiemann reaction conditions using $CHCl_3$ and aqueous $NaOH$ at $340\text{ K}$. Determine the correct decreasing order of their initial reaction rates and the exact nature of the attacking electrophile in the rate-determining step.

Phenol is treated with $\ce{CHCl3}$ and aqueous $\ce{NaOH}$ at $340\text{ K}$ to form an intermediate mixture containing compound $\textbf{P}$ as the major organic species. Without isolating $\textbf{P}$, an excess of acetone is added to the strongly basic reaction mixture and heated. Subsequent careful acidification of the mixture yields compound $\textbf{Q}$ as the major product.

Identify the IUPAC name and stereochemistry of compound $\textbf{Q}$.

Compound \textbf{X} (3-hydroxybenzoic acid) is subjected to two parallel reaction pathways:

Pathway I: \textbf{X} is treated with $\ce{CHCl3}$ and aqueous $\ce{NaOH}$ at $340\text{ K}$, followed by careful acidification to yield the major product \textbf{P}.

Pathway II: \textbf{X} is treated with $\ce{CH3COCl}$ (1 eq.) and excess anhydrous $\ce{AlCl3}$ at $298\text{ K}$, followed by acidic workup to yield the major product \textbf{Q}.

Based on the principles of electrophilic aromatic substitution and functional group reactivity, identify \textbf{P} and \textbf{Q}.

Phenol is treated with $CHCl_3$ and excess aqueous $NaOH$ at $340\text{ K}$. After complete consumption of $CHCl_3$, the resulting reaction mixture containing the sodium salt of the major product $P$ is divided into two equal aliquots, $X$ and $Y$. Aliquot $X$ is directly treated with aniline ($\ce{C6H5NH2}$) at $298\text{ K}$. Aliquot $Y$ is first adjusted to a pH of $4.5$ using dilute $HCl$, and then treated with aniline at $298\text{ K}$. Both mixtures are subsequently subjected to a standard mild aqueous workup. Identify the major organic products isolated from aliquots $X$ and $Y$, respectively.

Consider the following reaction sequence starting from 1-chloro-1-methylcyclopentane:

$\text{1-chloro-1-methylcyclopentane} \xrightarrow[\Delta]{\ce{NaOEt / EtOH}} \text{Major Product (B)}$

$\text{(B)} \xrightarrow[2. \ce{Me2S}]{1. \ce{O3}, 195\text{ K}} \text{(C)}$

$\text{(C)} \xrightarrow[2. \ce{H3O+}]{1. \ce{I2} \text{ (excess)}, \ce{NaOH}, \Delta} \text{Yellow precipitate} + \text{(D)}$

Identify the IUPAC name of the final organic product (D).

An organic chemist aims to synthesize the diaryl ether 1-methoxy-4-(4-nitrophenoxy)benzene (Compound $\textbf{W}$) and the benzyl aryl ether 1-fluoro-4-((4-nitrophenoxy)methyl)benzene (Compound $\textbf{Z}$).

The following synthetic pathways are evaluated: \textbf{Path I:} \ce{1-chloro-4-methoxybenzene} + sodium 4-nitrophenoxide $\xrightarrow{\text{DMF, } 150^\circ\text{C}}$ \textbf{Path II:} \ce{1-chloro-4-nitrobenzene} + sodium 4-methoxyphenoxide $\xrightarrow{\text{DMF, } 150^\circ\text{C}}$ \textbf{Path III:} \ce{1-(chloromethyl)-4-fluorobenzene} + sodium 4-nitrophenoxide $\xrightarrow{\text{DMF, } 25^\circ\text{C}}$

Which of the following statements correctly identifies the successful pathways and their corresponding mechanisms?

An optically pure alcohol, $(S)$-3-methylhexan-3-ol (Compound P), is treated with sodium metal to form an intermediate Q. Q is subsequently reacted with excess methyl iodide to yield an ether, R. Compound R is then treated with one equivalent of anhydrous HI at 298 K to produce an alkyl halide S and an alcohol T. Which of the following correctly identifies the major products S and T, and the stereochemical nature of S?

An organic salt, $N$-(2-bromoethyl)anilinium bromide (1.0 equivalent), is treated with exactly 1.0 equivalent of sodium ethoxide (\ce{NaOEt}) in absolute ethanol (\ce{EtOH}) at 298 K. The reaction mixture is stirred for a short duration. Which of the following represents the major organic species present in the reaction mixture?

Consider the reaction of 1-chloro-1,1-diphenylpropan-2-one with an excess of sodium methoxide in methanol at 298 K. What is the major organic product formed?

Consider the reaction of phenyl neopentyl ether ($\ce{Ph-O-CH2-C(CH3)3}$) with excess concentrated $\ce{HI}$ at $373\text{ K}$. Identify the major organic products formed.

An optically active haloalkane $\textbf{X}$, \ce{CH3CH(Br)C(CH3)3}, is treated with potassium \textit{tert}-butoxide in \textit{tert}-butanol at $350\text{ K}$ to yield a major organic product $\textbf{Y}$. Subsequent treatment of $\textbf{Y}$ with anhydrous \ce{HI} yields compound $\textbf{Z}$ as the major product. Which of the following correctly identifies $\textbf{Y}$ and $\textbf{Z}$?

Consider the cleavage of diethyl ether ($\ce{Et2O}$) at 298 K using sodium halide salts in pure carboxylic acid solvents. The cleavage proceeds via the initial protonation of the ether followed by a bimolecular nucleophilic attack ($S_N2$) by the halide ion ($\ce{X-}$):

Step 1: $\ce{Et2O + HA \rightleftharpoons Et2OH+ + A-}$ (fast equilibrium, constant $K_{eq}$) Step 2: $\ce{Et2OH+ + X- \rightarrow EtX + EtOH}$ (rate-determining step, rate constant $k_X$)

Reaction 1: 1.0 M $\ce{NaI}$ and 1.0 M $\ce{Et2O}$ dissolved in pure Chloroacetic acid (CAA). Reaction 2: 1.0 M $\ce{NaBr}$ and 1.0 M $\ce{Et2O}$ dissolved in pure Trichloroacetic acid (TCA).

Given the following parameters:

• $pK_a$ of $\ce{Et2OH+} = -3.5$
• $pK_a$ of TCA $= 0.5$
• $pK_a$ of CAA $= 2.5$
• The nucleophilic rate constant ratio $k_I / k_{Br} = 40$.

Assume the given $pK_a$ values accurately reflect the relative thermodynamic acidities in these solvent systems. Furthermore, assume the molar concentration of the solvent $[\ce{HA}]$ is identical in both reactions, autoionization of the solvents is negligible, complete dissociation of the sodium salts, and $\ce{Et2O}$ is the only significant base present (its concentration remains approximately 1.0 M).

What is the ratio of the initial rates of cleavage ($r_1 / r_2$) for Reaction 1 compared to Reaction 2?

An optically pure sample of $(R)\text{-2-methoxybutane}$ is heated with excess concentrated $\ce{HI}$ at $373\text{ K}$. The reaction yields methyl iodide and a chiral alkyl halide $\mathbf{X}$. Which of the following best describes the stereochemical composition of $\mathbf{X}$?

Consider the acid-catalyzed rearrangement of \ce{2,2-dimethyl-1-phenylpropane-1,3-diol} under heating with catalytic \ce{H2SO4}. Assuming the reaction is driven by thermodynamic control to its most stable final product, identify the major organic product formed.

Consider the specific stereoisomer of 2-amino-5-(tert-butyl)-1-phenylcyclohexan-1-ol where, in its most stable chair conformation, the \textit{tert}-butyl, phenyl, and amino groups are all equatorial, and the hydroxyl group is axial. This compound is treated with \ce{NaNO2} and aqueous \ce{HCl} at $273\text{ K}$. Identify the major organic product formed.

Compound \textbf{P}, 2-methyl-1,1-diphenylpropane-1,2-diol, is treated with a catalytic amount of anhydrous $p$-toluenesulfonic acid (TsOH) in excess ethanol at 298 K. What is the major organic product formed?

Compound \textbf{X} is 1-(1-hydroxycyclobutyl)-1-phenylethan-1-ol. It undergoes two separate reactions: Reaction 1: \textbf{X} $\xrightarrow{\text{cat. } H_2SO_4, \Delta}$ \textbf{P} (Major Product) Reaction 2: \textbf{X} $\xrightarrow{HIO_4, 298\text{ K}}$ \textbf{Q} + \textbf{R} Identify \textbf{P}, and the mixture of \textbf{Q} + \textbf{R}.

An organic compound \textbf{X}, 1,1-bis(4-nitrophenyl)-2-methylpropane-1,2-diol, is heated with concentrated $H_2SO_4$. Assuming standard Pinacol-Pinacolone rearrangement conditions, identify the major product formed.

Let $t_i$ represent the kinetic classification of alcohol $i$ in the Lucas test (conc. \ce{HCl} + anhydrous \ce{ZnCl2}) at 298 K: $t_i = 1$ if turbidity appears immediately. $t_i = 2$ if turbidity appears after 5-10 minutes. $t_i = 3$ if no turbidity appears at 298 K.

Let $h_i$ represent the number of $\beta$-hydrogen atoms in the major alkyl chloride product formed when alcohol $i$ is heated with Lucas reagent for a prolonged period.

Consider the following three alcohols: \textbf{P}: 3-Methylbutan-2-ol \textbf{Q}: 2,2-Dimethylpropan-1-ol \textbf{R}: 1-Methylcyclopentan-1-ol

Calculate the value of the expression: $\Sigma (t_i \times h_i) = (t_P \times h_P) + (t_Q \times h_Q) + (t_R \times h_R)$.

Compound \textbf{P} is methyl 4,5-epoxy-5-methylhexanoate. \textbf{P} undergoes the following reaction sequence:

1. \textbf{P} is treated with excess \ce{LiAlH4} in dry THF followed by acidic workup to yield compound \textbf{Q}.
2. \textbf{Q} is reacted with 1 equivalent of acetyl chloride (\ce{CH3COCl}) in the presence of pyridine at $0^\circ\text{C}$ to yield the major product \textbf{R}.
3. \textbf{R} is treated with Lucas reagent (\ce{ZnCl2} / conc. \ce{HCl}) at $25^\circ\text{C}$ to yield compound \textbf{S}.

Identify the IUPAC name of compound \textbf{S}.

Consider the organic compound $\mathbf{X}$, which is 5-chloro-2-(hydroxymethyl)-4-nitrophenol. $\mathbf{X}$ undergoes the following reaction sequence:

Step 1: $\mathbf{X}$ is treated with Lucas reagent (anhydrous $\ce{ZnCl2}$ and conc. $\ce{HCl}$) at $298\text{ K}$ to yield the major product $\mathbf{Y}$.

Step 2: $\mathbf{Y}$ is reacted with excess $\ce{NaOCH3}$ in $\ce{CH3OH}$ at $330\text{ K}$, followed by mild acidification with dilute $\ce{HCl}$, to yield the major product $\mathbf{Z}$.

Identify the correct IUPAC name for the final product $\mathbf{Z}$.

Consider the compound \textbf{X}, 5-hydroxyhexan-2-one. It is subjected to three different reducing conditions to yield major organic products \textbf{P}, \textbf{Q}, and \textbf{R}:

Reaction 1: \textbf{X} $\xrightarrow{Zn(Hg),\text{ conc. } HCl,\ \Delta}$ \textbf{P}

Reaction 2: \textbf{X} $\xrightarrow{NH_2NH_2,\ KOH,\ \text{ethylene glycol},\ \Delta}$ \textbf{Q}

Reaction 3: \textbf{X} $\xrightarrow{1.\ LiAlH_4,\ \text{dry ether} \quad 2.\ H_3O^+}$ \textbf{R}

Identify the major products \textbf{P}, \textbf{Q}, and \textbf{R}.