Draw the product formed when pentanal (CH3CH2CH2CH2CHO) is treated with each reagent. With some reagents, no reaction occurs.
a. NaBH4, CH3OH
b. [1] LiAIH4; [2] H2O
c. H2, Pd-C
d. PCC
e. Na2Cr2O7, H2SO4, H2O
f. Ag2O, NH4OH
g. [1] CH3MgBr; [2] H2O
h. [1] C6H5Li; [2] H2O
i. [1] (CH3)2CuLi; [2] H2O
j. [1] HC ≡ CNa; [2] H2O
k. [1] CH ≡ CLi; [2] H2O
l. The product in (a), then TBDMS-CI, imidazole
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