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1) What type of intermediate forms when a solvated electron adds to an alkyne? a

ID: 1035390 • Letter: 1

Question

1) What type of intermediate forms when a solvated electron adds to an alkyne? a. Neutral radical b. Radical cation c. Cation d. Anion e. Radical anion 2) Which of the following sequences of reactions will convert an internal alkene into an alkyne? a. 1. mCPBA; 2. NaNH2 (2 eq.); 3. NH4CI b. 1. Br2; 2. NaNH2 (2 eq); 3. NH4CI c. 1. NaOH; 2. HCI d. 1. 03: 2. Zn. AcOH: 3. Na NH2 (2 eq.); 4. NHaci e. 1. HCI (cat.), H20; 2. NaNH2 (2 eq.); 3. NH4CI ) Which of the following reactions is syn stereospecific? a. Halogenation of an alkyne b. lonic hydrohalogenation of an alkyne c. Lindlar hydrogenation d. Radical hydrohalogenation of an alkyne e. Ozonolysis of an alkyne

Explanation / Answer

1. Option E, radical anion since it is an example for Birch reduction of alkyne with Na/liquid NH3

2. Option B, bromination of alkene gives trans vicinal dibromo alkane followed by with NaNH2, and NH4Cl results elimination to yield internal alkyne.

3. Option C, Lindlar's catalyst reduces the internal alkyne into cis alkene stereospecifically.