Identify the reagents necessary to accomplish the following transformations: Cho

Question

Identify the reagents necessary to accomplish the following transformations:

Choose from the following list of reagents:

Enter the correct letter for each step of the reaction in the boxes below.
(Reagents cannot be used more than once.)

Step A:

Step B:

Step C:

a
1) EtMgBr
2) H2O b
H2, Pt c
PCC, CH2Cl2 d
1) TsCl, pyridine
2) t-BuOK e
1) 9-BBN
2) H2O2, NaOH f
1) MeMgBr
2) H2O g
Na2Cr2O7, H2SO4, H2O h
TsCl, pyridine i
1) BH3THF
2) H2O2, NaOH j
H2, Lindlar's catalyst k
Na2Cr2O7 l
1) t-BuOK
2) TsCl, pyridine

Explanation / Answer

Reagent for step A: i) 1) BH3, THF 2) H2O2, NaOH

Explanation: Hydroboration - oxidation of alkyne with BH3, THF and H2O2, NaOH produces aldehyde as product.

Reagent for step B: f) 1) MeMgBr 2) H2O

Explanation: Reaction of aldehyde with MeMgBr produces alcohol as product.

Reagent for step C: c) PCC, CH2Cl2

Explanation; oxidaiton of secondary alcohol with PCC, CH2Cl2 produces ketone as product.

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