1. Which substance is NOT an aldehyde? D (B) NH (C) 2. Which substance produced
ID: 1029989 • Letter: 1
Question
1. Which substance is NOT an aldehyde? D (B) NH (C) 2. Which substance produced the following infrared spectrum BELOW, LEFT)? (A) benzoic acid (B) benzaldehyde (C) dipherylketone --(D)benzyl alcohol 9.96 a) 7.78Hd. J-84 Ho 34 28d J-84 3073 3. Which compound is consistent with the H1-NMR spectrum shown (ABOVE, RIGHT)? (A) o-ethyl benzaldehyde (B) m-ethyl benzaldehyde (C) p-cthyl benzaldehyde (D) p-cthyl benzoic acid 4. Which compound is least likely to form an alcohol upon reaction with one equivalent of phenylithium? H (D) H (C) 5. Which ether is least likely to undergo acidic cleavage with H-1? (B) O *6. Which compound is the strongest acid? 0 0 Eto OOH (B) () OH (D) Eto 7. Which compound will react with acetone the fastest? (A) HC 8. Which compound has the strongest C-O bond? IR frequencies (em') are provided with each compound? (C) 1717 0 1747 1783 1702 9. Which compound is unlikely to form a cyclic product. 0 #10, which nd is the most reactive toward cyanohydrin formation? 0 H (B) H (C) MeOExplanation / Answer
1. Option B, it is an amide. Aldehyde has H-C=O group.
2. Option A, benzoic acid since it has peaks at 3073, 2564 and 1689 for =CH, OH and C=O stretches.
3. Option C, since it since it has signal at 9.96 for aldehyde proton and signals at aromatic region are for Para substitution
4. Option C, since it is less Electrophilic and PhLi is Nucleophilic reagent and it needs more electrophilic reagent.
5. Option B, since it is not an ether. It is an Acetal.
6. Option D, OEt groups at meta position acts as EWG, hence they increase the acidity.
7. Option C, since it is more Nucleophilic
8. Option A, since it has more IR value. Greater the IR value greater the strength of C-O bond.
9. Option C, it won't form cyclic product, remaining all forms A-lactone, B- Imine, D-Lactam
10. Option D, since it has EWG, It increases the electrophilicity. Formation of caynohydrin is Nucleophilic Addition and it needs more electrophilic center. Hence D.
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