Draw the product formed when pentanal (CH;CH,CH2CH;CHO) is treated with each reagent. With some reagents, no reaction occurs. a. NaBH4, CH,OH b. [1] LIAIH4; (2] H20 c. H2, Pd-C d. PCC e. NazCr,07, H2SO4, H2O f. Ag,0, NH,OH g. [1) CH,MgBr; (2] H2O h. [1] CęH,Li; [2] H20 i. [1] (CH3),CuLi; (2] H2O j. [1] HC=CNa; [2] H2O k. [1] CH;C=CLi; [2] H2O I. The product in (a), then TBDMS-CI, imidazole

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Draw the product formed when pentanal (CH;CH,CH2CH;CHO) is treated with each reagent. With some reagents, no reaction
occurs.
a. NaBH4, CH,OH
b. [1] LIAIH4; (2] H20
c. H2, Pd-C
d. PCC
e. NazCr,07, H2SO4, H2O
f. Ag,0, NH,OH
g. [1) CH,MgBr; (2] H2O
h. [1] CęH,Li; [2] H20
i. [1] (CH3),CuLi; (2] H2O
j. [1] HC=CNa; [2] H2O
k. [1] CH;C=CLi; [2] H2O
I. The product in (a), then TBDMS-CI, imidazole
Transcribed Image Text:Draw the product formed when pentanal (CH;CH,CH2CH;CHO) is treated with each reagent. With some reagents, no reaction occurs. a. NaBH4, CH,OH b. [1] LIAIH4; (2] H20 c. H2, Pd-C d. PCC e. NazCr,07, H2SO4, H2O f. Ag,0, NH,OH g. [1) CH,MgBr; (2] H2O h. [1] CęH,Li; [2] H20 i. [1] (CH3),CuLi; (2] H2O j. [1] HC=CNa; [2] H2O k. [1] CH;C=CLi; [2] H2O I. The product in (a), then TBDMS-CI, imidazole
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