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Multiple Choice Questions
1. Which of the following reactants on reaction with conc. $\text{NaOH}$ followed by acidification gives the following lactone as the only product? [JEE Main 2006]
(a) 
(b) 
(c) $\text{CHO-CH}_2\text{-CH}_2\text{-CH}_2\text{-CHO}$
(d) 
Answer: (c)
Explanation: $\text{CHO-CH}_2\text{-CH}_2\text{-CH}_2\text{-CHO} \xrightarrow{\text{conc. KOH}} \text{HO-CH}_2\text{-CH}_2\text{-CH}_2\text{-CH}_2\text{-COOK} \xrightarrow{\text{H}^+} \text{Lactone (F)}$
2. The smallest ketone and its next homologue are reacted with $\text{NH}_2\text{OH}$ to form oxime. [JEE Main 2006]
(a) Two different oximes are formed
(b) Three different oximes are formed
(c) Two oximes are optically active
(d) All oximes are optically active
Answer: (b)
Explanation: Smallest ketone is acetone ($\text{CH}_3\text{COCH}_3$) which forms 1 oxime ($\text{CH}_3\text{-C(}=\text{NOH)-CH}_3$). Next homologue is $\text{CH}_3\text{COCH}_2\text{CH}_3$ which forms 2 syn and anti oximes (geometrical isomers). Total = 3 oximes.
3. Cyclohexene on ozonolysis followed by reaction with zinc dust and water gives compound E. Compound E on further treatment with aqueous $\text{KOH}$ yields compound F. Compound F is [JEE 2007 P-II]
(a) 
(b) 
(c) 
(d) 
Answer: (a)
Explanation: Cyclohexene $\xrightarrow{\text{O}_3, \text{Zn/H}_2\text{O}} \text{OHC-(CH}_2\text{)}_4\text{-CHO} \text{ (E)} \xrightarrow{\text{aq. KOH}} \text{1-cyclopentenecarbaldehyde (F)}$.
4. The number of aldol reaction(s) that occurs in the given transformation is [JEE 2012 P-I]
$$\text{K}_2\text{CO}_3 + \text{HCHO} + \text{CH}_3\text{CHO} \longrightarrow \text{C(CH}_2\text{OH)}_4$$
(a) 1
(b) 2
(c) 3
(d) 4
Answer: (c)
Explanation: 1, 2, 3 are aldol reactions (3 acidic $\alpha\text{-H}$ atoms of acetaldehyde undergo cross-aldol with formaldehyde) while the 4th step is a Cannizzaro reaction.
5. The major product H of the given reaction sequence is [JEE 2012 P-II]
$$\text{CN}^- \xrightarrow{\text{95\% H}_2\text{SO}_4, \text{ Heat}} \text{G} \xrightarrow{\text{CH}_3\text{-CH}=\text{C(CH}_3\text{)-CO-CH}_3} \text{H}$$
(a) $\text{CH}_3\text{-CH}=\text{C(CH}_3\text{)-COOH}$
(b) $\text{CH}_3\text{-CH}=\text{C(CH}_3\text{)-CN}$
(c) $\text{CH}_3\text{-CH}_2\text{-C(OH)(CH}_3\text{)-COOH}$
(d) $\text{CH}_3\text{-CH}=\text{C(CH}_3\text{)-CO-NH}_2$
Answer: (a)
Explanation: Hydrolysis of ester/nitrile precursor yields $\text{CH}_3\text{-CH}=\text{C(CH}_3\text{)-COOH}$.
6. After completion of the reactions (I and II), the organic compound(s) in the reaction mixtures is (are) [JEE Adv. 2013 P-II]
Reaction I: $\text{CH}_3\text{COCH}_3 + \text{Br}_2 (1.0\text{ mol}) \xrightarrow{\text{CH}_3\text{COOH}}$
Reaction II: $\text{CH}_3\text{COCH}_3 + \text{Br}_2 (1.0\text{ mol}) \xrightarrow{\text{aqueous NaOH}}$
(a) Reaction I: P and Reaction II: P
(b) Reaction I: U, acetone and Reaction II: Q, acetone
(c) Reaction I: T, U, acetone and Reaction II: P
(d) Reaction I: R, acetone and Reaction II: S, acetone
Answer: (c)
Explanation: Solve as per law of limiting reagent. Monobromination in acid medium gives mono, di-bromo acetone mixture (T, U, acetone left). Base-promoted haloform reaction converts 1 mole of acetone into haloform P ($\text{CHBr}_3$).
7. The major product in the following reaction is [JEE Adv. 2014 P-II]
$$\text{C}_6\text{H}_5\text{CHO} + \text{CH}_3\text{-MgBr} \xrightarrow{\text{1. dry ether, 0}^\circ\text{C}} \xrightarrow{\text{2. aqueous acid}} \text{Product}$$
(a) 
(b) 
(c) 
(d) 
Answer: (d)
Explanation: Nucleophilic addition of Grignard reagent to benzaldehyde followed by hydrolysis yields 1-phenylethanol.
8. Positive Tollen's test is observed for [JEE Adv. 2016 P-I]
(a) $\text{HO-CH}_2\text{-CH(OH)-CHO}$
(b) $\text{C}_6\text{H}_5\text{-CO-CH(OH)-C}_6\text{H}_5$
(c) $\text{C}_6\text{H}_5\text{-CHO}$
(d) $\text{CH}_3\text{-CO-CH}_3$
Answer: (a, b, c)
Explanation: Aldehydes and $\alpha$-hydroxyketones reduce Tollen's reagent to give a positive silver mirror test.
9. The major product obtained in the following reaction is [JEE Adv. 2016 P-I]
$$\text{Substituted Lactone} \xrightarrow{\text{DIBAL-H, Toluene, -78}^\circ\text{C}} \xrightarrow{\text{H}_2\text{O}}$$
(a) 
(b) 
(c) 
(d) 
Answer: (c)
Explanation: DIBAL-H is an electrophilic reducing agent that reduces lactones partially to hydroxy-aldehydes (hemiacetal intermediate).
10. The correct sequence of reagents for the following conversion will be [JEE Adv. 2016 P-I]
$$\text{Keto-aldehyde} \longrightarrow \text{Keto-ester / Hydroxy-ester derivative}$$
(a) $[\text{Ag(NH}_3)_2]^+\text{OH}^-$, $\text{CH}_3\text{MgBr}$, $\text{H}^+/\text{CH}_3\text{OH}$
(b) $[\text{Ag(NH}_3)_2]^+\text{OH}^-$, $\text{H}^+/\text{CH}_3\text{OH}$, $\text{CH}_3\text{MgBr}$
(c) $\text{CH}_3\text{MgBr}$, $\text{H}^+/\text{CH}_3\text{OH}$, $[\text{Ag(NH}_3)_2]^+\text{OH}^-$
(d) $\text{CH}_3\text{MgBr}$, $[\text{Ag(NH}_3)_2]^+\text{OH}^-$, $\text{H}^+/\text{CH}_3\text{OH}$
Answer: (b)
Explanation: Selective oxidation of $-\text{CHO}$ with Tollen's reagent to $-\text{COOH}$, followed by esterification $\text{H}^+/\text{CH}_3\text{OH}$, and then selective Grignard addition to ester/keto group.
11. The compound R is [JEE Adv. 2018 P-I]
(a) 
(b) 
(c) 
(d) 
Answer: (a)
Explanation: Ozonolysis of compound P ($\text{C}_{11}\text{H}_{12}\text{O}_2$) yields ketone and oxidized products, leading to intermediate Q and final compound R upon treatment with $\text{Mg, Et}_2\text{O}$ followed by $\text{CO}_2$ and acid hydrolysis.
12. The major product of the following reaction is: [JEE Main 2019]
$$\text{4-bromo-cyclohexanone} \xrightarrow{\text{NaBH}_4, \text{MeOH, 25}^\circ\text{C}}$$
(a) 
(b) 
(c) 
(d) 
Answer: (d)
Explanation: $\text{NaBH}_4$ selectively reduces the carbonyl group to a secondary alcohol without affecting the halogen substituent.
13. The major product of the following reactions: [JEE Main 2019]
$$\text{Alkoxy-alkene compound} \xrightarrow{\text{Conc. HBr (excess), Heat}}$$
(a) 
(b) 
(c) 
(d) 
Answer: (d)
Explanation: Ether cleavage with excess conc. $\text{HBr}$ gives phenol/alcohol and alkyl bromide, followed by electrophilic addition of $\text{HBr}$ across the double bond.
14. The major product of the following reaction is: [JEE Main 2019]
$$\text{Halo-carbonyl compound} \xrightarrow{(i)\text{ }t\text{-BuOK}} \xrightarrow{(ii)\text{ Conc. H}_2\text{SO}_4 / \Delta}$$
(a) 
(b) 
(c) 
(d) 
Answer: (d)
Explanation: Dehydrohalogenation via $E_2$ reaction using $t\text{-BuOK}$ followed by acid-catalyzed dehydration gives the conjugated dienone product.
15. Which of the following compounds will show the maximum enol content? [JEE Main 2019]
(a) $\text{CH}_3\text{COCH}_2\text{COCH}_3$
(b) $\text{CH}_3\text{COCH}_3$
(c) $\text{CH}_3\text{COCH}_2\text{CONH}_2$
(d) $\text{CH}_3\text{COCH}_2\text{COOC}_2\text{H}_5$
Answer: (a)
Explanation: Acetylacetone ($\text{CH}_3\text{COCH}_2\text{COCH}_3$) forms a highly stable enol tautomer stabilized by intramolecular hydrogen bonding and a conjugated six-membered ring system.
16. The major product obtained in the following reaction is [JEE Main 2019]
$$\text{Dicarbonyl compound} \xrightarrow{\text{NaOH}, \Delta}$$
(a) 
(b) 
(c) 
(d) 
Answer: (d)
Explanation: Intramolecular aldol condensation of the dicarbonyl compound under basic conditions yields the stable conjugated cyclic ketone.
17. The major of the following reaction is: [JEE Main 2019]
$$\text{Aromatic compound} \xrightarrow{\text{AlCl}_3, \Delta}$$
(a) 
(b) 
(c) 
(d) 
Answer: (d)
Explanation: Intramolecular Friedel-Crafts acylation catalyzed by $\text{AlCl}_3$ leads to ring closure giving a fused bicyclic/polycyclic ketone.
18. The major product formed in the following: [JEE Main 2019]
$$\text{Keto-aldehyde compound} \xrightarrow{\text{dil. NaOH}}$$
(a) 
(b) 
(c) 
(d) 
Answer: (a)
Explanation: Aldehyde group reacts at a faster rate than ketone during aldol condensation, and steric factors direct enolate addition to form the major self/cross aldol product.
19. The major product of the following reaction is: [JEE Main 2019]
$$\text{Aryl ether} \xrightarrow{(i)\text{ AlCl}_3\text{ (anhyd)}} \xrightarrow{(ii)\text{ H}_2\text{O}}$$
(a) 
(b) 
(c) 
(d) 
Answer: (b)
Explanation: Electrophilic aromatic substitution followed by 1,2-hydride shift and intramolecular Friedel-Crafts alkylation/acylation.
20. The major product of the following reaction is [JEE Main 2019]
$$\text{Cyclic hydroxy-ketone} \xrightarrow{(i)\text{ aq. NaOH}} \xrightarrow{(ii)\text{ CH}_3\text{I}}$$
(a) 
(b) 
(c) 
(d) 
Answer: (d)
Explanation: Deprotonation by $\text{NaOH}$ forms the acidic enolate, which undergoes alkylation ($S_N2$) with $\text{CH}_3\text{I}$ at the $\alpha$-carbon.
Integer and Subjective
21. The major product obtained in the following reaction is: [JEE Main 2019]
$\longrightarrow \xrightarrow{\text{NaOEt} / \Delta}$
(a) Product A
(b) Product B
(c) Product C
(d) Product D
Answer: (d)
Explanation: Reaction proceeds via intramolecular condensation under basic conditions ($\text{NaOEt} / \Delta$) to yield the conjugated cyclic ketone as the major product.
22. The major product of the following reaction is: [JEE Main 2019]
$\xrightarrow[\text{(ii) alc KOH}]{\text{(i) HBr}}$
(a) Product A
(b) Product B
(c) Product C
(d) Product D
Answer: (a)
Explanation:
$$\xrightarrow{\text{HBr}} \text{Brominated intermediate} \xrightarrow{\text{alc. KOH}} \text{Elimination product} \rightleftharpoons \text{Tautomer}$$
23. The major product of the following reaction is: [JEE Main 2019]
$$\xrightarrow[\text{(ii) } \text{H}_2\text{SO}_4\text{ (dil)}]{\text{(i) } \text{KMnO}_4 / \text{KOH}, \Delta}$$
(a) Product A
(b) Product B
(c) Product C
(d) Product D
Answer: (b)
Explanation: Alkaline $\text{KMnO}_4$ oxidation of alkyl/acyl side chains followed by acidification yields dicarboxylic acid product.
24. The major product of the following reaction is: [JEE Main 2019]
$$\xrightarrow[\text{(2) } \text{AlCl}_3\text{ (anhyd.)}]{\text{(1) } \text{Cl}_2 / \text{CCl}_4}$$
(a) Product A
(b) Product B
(c) Product C
(d) Product D
Answer: (b)
Explanation: Chlorination followed by intramolecular electrophilic aromatic substitution ($\text{AlCl}_3$) gives the cyclized chloro ketone product.
25. In the following reactions, products A and B are: [JEE Main 2019]
$$\text{Reactant} \xrightarrow{\text{dil NaOH}} [\text{A}] \xrightarrow[\Delta]{\text{H}_3\text{O}^+} [\text{B}]$$
(a) A and B option a
(b) A and B option b
(c) A and B option c
(d) A and B option d
Answer: (d)
Explanation: Dilute $\text{NaOH}$ induces aldol reaction to give aldol adduct $[\text{A}]$, which undergoes dehydration upon heating in acidic medium to yield $\alpha,\beta$-unsaturated ketone $[\text{B}]$.
26. In the following reaction: $\text{Aldehyde} + \text{Alcohol} \xrightarrow{\text{HCl}} \text{Acetal}$ [JEE Main 2019]
The best combination is:
(a) $\text{HCHO}$ and $\text{MeOH}$
(b) $\text{HCHO}$ and $t\text{BuOH}$
(c) $\text{CH}_3\text{CHO}$ and $\text{MeOH}$
(d) $\text{CH}_3\text{CHO}$ and $t\text{BuOH}$
Answer: (a)
Explanation: Rate of acetal formation is inversely proportional to steric crowding of aldehyde ($\text{Rate} \propto \frac{1}{\text{steric crowding}}$). $\text{HCHO}$ is least hindered, and $\text{MeOH}$ is unhindered primary alcohol.
27. The major product of the following reaction is: $\xrightarrow{\text{NaBH}_4 / \text{EtOH}}$ [JEE Main 2019]
(a) Product A
(b) Product B
(c) Product C
(d) Product D
Answer: (d)
Explanation: $\text{NaBH}_4$ cannot reduce $\text{C}=\text{C}$ double bonds, but selectively reduces carbonyl group ($-\text{C}=\text{O}$) to alcohol ($-\text{OH}$).
28. The aldehydes which will not form Grignard product with one equivalent Grignard reagents are: [JEE Main 2019]
(a) (B), (C), (D)
(b) (B), (D)
(c) (B), (C)
(d) (C), (D)
Answer: (b)
Explanation: Compounds containing acidic hydrogens (like $-\text{OH}$ or $-\text{COOH}$) undergo fast acid-base proton transfer with Grignard reagent ($\text{RMgX} + \text{H}^+ \longrightarrow \text{RH}$) rather than nucleophilic addition to carbonyl.
29. $$\text{Starting material} \xrightarrow[\text{(2) } \text{AgNO}_3/\text{NH}_4\text{OH}]{\text{(1) } \text{HgSO}_4 / \text{dil H}_2\text{SO}_4} \text{'Q'} \xrightarrow[\text{(2) } \text{AlCl}_3]{\text{(1) } \text{SOCl}_2 / \text{Py}} \text{R} \xrightarrow{\text{ZnHg / HCl}} \text{S}$$ [JEE Adv. 2019 P-II]
(a) Option a
(b) Option b
(c) Option c
(d) Option d
Answer: (a, b)
Explanation: Hydration of terminal alkyne gives aldehyde/ketone, oxidation with Tollen's gives carboxylic acid $Q$, chlorination and Friedel-Crafts acylation gives cyclic ketone $R$, and Clemmensen reduction ($\text{ZnHg/HCl}$) reduces ketone to hydrocarbon $S$.
Matrix Match/Column Match
30. Match the compounds/ions in Column I with their properties/reactions in Column II [JEE 2007 P-II]
(a) A$\rightarrow$1, 2, 3; B$\rightarrow$1, 2; C$\rightarrow$1, 3; D$\rightarrow$2, 3
(b) A$\rightarrow$1, 3; B$\rightarrow$1; C$\rightarrow$1, 2, 4; D$\rightarrow$2, 3
(c) A$\rightarrow$1, 2, 3; B$\rightarrow$3; C$\rightarrow$1, 2, 4; D$\rightarrow$2, 3
(d) A$\rightarrow$1, 2, 3; B$\rightarrow$2; C$\rightarrow$1, 3, 4; D$\rightarrow$2, 3
Answer: (d)
Explanation: A$\rightarrow$1, 2, 3; B$\rightarrow$2; C$\rightarrow$1, 3, 4; D$\rightarrow$2, 3.
Terminal alkynes give precipitate with ammoniacal $\text{AgNO}_3$ ($\text{Ag}^+$ precipitate). Aldehydes give 2,4-DNP precipitate and undergo cyanohydrin formation with $\text{CN}^-$.
31. Match the reactions in Column I with appropriate options in Column II. [JEE 2010 P-II]
(a) A$\rightarrow$1, 4, 5; B$\rightarrow$1; C$\rightarrow$1, 3; D$\rightarrow$3
(b) A$\rightarrow$2, 4, 5; B$\rightarrow$2; C$\rightarrow$1, 3; D$\rightarrow$5
(c) A$\rightarrow$3, 4, 5; B$\rightarrow$5; C$\rightarrow$1, 2; D$\rightarrow$3
(d) A$\rightarrow$3, 4, 1; B$\rightarrow$2; C$\rightarrow$1, 5; D$\rightarrow$1, 3
Answer: (c)
Explanation: A$\rightarrow$3, 4, 5; B$\rightarrow$5; C$\rightarrow$1, 2; D$\rightarrow$3.
(A) Electrophilic substitution and coupling reaction via carbocation.
(B) Pinacol-pinacolone rearrangement involving carbocation intermediate.
(C) Nucleophilic addition to carbonyl forming racemic mixture of enantiomers.
(D) Nucleophilic substitution reaction.
32. The correct match between Column - I and Column - II is: [JEE Main 2019]
(a) A$\rightarrow$2; B$\rightarrow$3; C$\rightarrow$1
(b) A$\rightarrow$2; B$\rightarrow$1; C$\rightarrow$3
(c) A$\rightarrow$3; B$\rightarrow$1; C$\rightarrow$2
(d) A$\rightarrow$3; B$\rightarrow$2; C$\rightarrow$1
Answer: (d)
Explanation: Benzaldehyde is adsorbate (3), Alumina is adsorbent (2), Acetonitrile is mobile phase (1).
Paragraph
Paragraph for Question Nos. 33 to 35
33. The structure of the product I is [JEE 2008 P-I]
(a) Structure A
(b) Structure B
(c) Structure C
(d) Structure D
Answer: (d)
Explanation: $\text{CH}_3\text{CH}_2\text{C}\equiv\text{CCH}_2\text{CHO} \xrightarrow[\text{2. PBr}_3]{\text{1. NaBH}_4} \text{CH}_3\text{CH}_2\text{C}\equiv\text{CCH}_2\text{CH}_2\text{Br}$ (I).
34. The structure of compounds J and K respectively are [JEE 2008 P-I]
(a) Structure J and K option a
(b) Structure J and K option b
(c) Structure J and K option c
(d) Structure J and K option d
Answer: (a)
Explanation: Compound I $\xrightarrow[\text{3. H}_3\text{O}^+]{\text{1. Mg/Ether, 2. CO}_2} \text{CH}_3\text{CH}_2\text{C}\equiv\text{CCH}_2\text{CH}_2\text{COOH}$ (J), $K = \text{SOCl}_2$.
35. The structure of product L is [JEE 2008 P-I]
(a) Structure A
(b) Structure B
(c) Structure C
(d) Structure D
Answer: (c)
Explanation: Partial hydrogenation of alkyne gives cis-alkene structure L.
Paragraph for Question Nos. 36 to 38
36. The structure of the carbonyl compound P is [JEE 2009 P-I]
(a) Structure A
(b) Structure B
(c) Structure C
(d) Structure D
Answer: (b)
Explanation: Methyl ketone P gives positive iodoform test.
37. The structure of the products Q and R, respectively, are [JEE 2009 P-I]
(a) Option a
(b) Option b
(c) Option c
(d) Option d
Answer: (a)
Explanation: Reaction of P with $\text{MeMgBr}$ followed by dehydration gives alkene Q. Ozonolysis ($\text{O}_3/\text{Zn, H}_2\text{O}$) of Q yields dicarbonyl compound R.
38. The structure of the product S is [JEE 2009 P-I]
(a) Structure A
(b) Structure B
(c) Structure C
(d) Structure D
Answer: (b)
Explanation: Intramolecular aldol condensation of dicarbonyl R in basic medium gives cyclic $\alpha,\beta$-unsaturated ketone product S.
Paragraph for Question Nos. 39 to 40
39. The compound K is [JEE 2012 P-II]
(a) Structure A
(b) Structure B
(c) Structure C
(d) Structure D
Answer: (c)
Explanation: Acid chloride undergoes Friedel-Crafts acylation ($\text{AlCl}_3$) to give tricyclic ketone K.
40. The compound I is [JEE 2012 P-II]
(a) Structure A
(b) Structure B
(c) Structure C
(d) Structure D
Answer: (a)
Explanation: Compound I is phthalic anhydride derivative which reacts with $(\text{CH}_3\text{CO})_2\text{O} / \text{CH}_3\text{COONa}$ via Perkin-type condensation to yield intermediate J.
Integer and Subjective
41. In the scheme given below, the total number of intramolecular aldol condensation products formed from 'Y' is [JEE 2010 P-I]
Answer: 1
Explanation: Intramolecular aldol condensation of Y leads selectively to 1 stable 6-membered enone product.
42. Consider all possible isomeric ketones, including stereoisomers of $\text{C}_5\text{H}_{10}\text{O}$. All these isomers are independently reacted with $\text{NaBH}_4$. The total number of ketones that give a racemic product(s) is/are [JEE Adv. 2014 P-I]
Answer: 5
Explanation: The possible isomeric ketones of $\text{C}_5\text{H}_{10}\text{O}$ are:
(1) $\text{CH}_3-\text{CH}_2-\text{CH}_2-\text{CO}-\text{CH}_3$ (gives racemic mixture on reduction with $\text{NaBH}_4$)
(2) $\text{CH}_3-\text{CH}_2-\text{CO}-\text{CH}_2-\text{CH}_3$ (achiral alcohol formed, no racemic mixture)
(3) $(\text{CH}_3)_2\text{CH}-\text{CO}-\text{CH}_3$ (gives racemic mixture on reduction with $\text{NaBH}_4$)
(4) $\text{CH}_3-\text{CH}(\text{CH}_3)-\text{CH}_2-\text{CO}-\text{CH}_3$ (gives racemic mixture)
(5) $\text{CH}_3-\text{CH}_2-\text{CH}(\text{CH}_3)-\text{CO}-\text{CH}_3$ (gives racemic mixture)
(6) Chiral ketone giving pair of diastereomers/racemic mixture.
Total number of ketones giving racemic product = 5.
43. Among the following, the number of reaction(s) that produce(s) benzaldehyde is [JEE Adv. 2015 P-II]
I. $\text{Ph-COCl} \xrightarrow{\text{H}_2, \text{Pd-BaSO}_4}$
II. $\text{Ph-CHCl}_2 \xrightarrow{\text{H}_2\text{O}, 100^\circ\text{C}}$
III. $\text{Ph-CN} \xrightarrow[\text{(ii) H}_3\text{O}^+]{\text{(i) DIBAL-H, Toluene, }-78^\circ\text{C}}$
IV. $\text{Ph-COOCH}_3 \xrightarrow[\text{(ii) H}_3\text{O}^+]{\text{(i) DIBAL-H, Toluene, }-78^\circ\text{C}}$
Answer: 4
Explanation: All 4 reactions yield benzaldehyde ($\text{PhCHO}$):
I. Rosenmund reduction of benzoyl chloride gives $\text{PhCHO}$.
II. Hydrolysis of benzal chloride gives $\text{PhCHO}$.
III. DIBAL-H reduction of benzonitrile gives $\text{PhCHO}$.
IV. DIBAL-H reduction of methyl benzoate at $-78^\circ\text{C}$ gives $\text{PhCHO}$.
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