Question

• 11.2 Practice Draw and name the product(s) [or just assign configuration if it's a FG we haven't yet covered] of the following reactions. Identify the nucleophile and electrophile in each reaction. Include the mechanisms. Describe the spectroscopic changes that occur (IR and NMRs). Assume all reactions below are SN2 (this will not remain true as you learn more later in this chapter). a. (S)-2-iodobutane + cyanide ion I b. (R)-2-bromopentane + hydroxide ion c. (S)-2-chloropentane + an acetylide ion of your choice 0 ?• Spectroscopic changes • reactant ? product F • IR: what disappears in the product IR that was there in the reactant IR? what appears in the product IR that was NOT there in the reactant IR? • $^{13}C$ NMR: ppm changes, # peaks changes • $^1H$ NMR: ppm changes, integration changes, splitting changes, # signals changes CN nitr ??

          • 11.2 Practice
Draw and name the product(s) [or just assign configuration if it's a FG we haven't yet
covered] of the following reactions. Identify the nucleophile and electrophile in each
reaction. Include the mechanisms. Describe the spectroscopic changes that occur (IR
and NMRs). Assume all reactions below are SN2 (this will not remain true as you learn
more later in this chapter).
a. (S)-2-iodobutane + cyanide ion
I
b. (R)-2-bromopentane + hydroxide ion
c. (S)-2-chloropentane + an acetylide ion of your choice
0
?• Spectroscopic changes
• reactant ? product
F
• IR: what disappears in the product IR that was there in the reactant IR?
what appears in the product IR that was NOT there in the reactant IR?
• $^{13}C$ NMR: ppm changes, # peaks changes
• $^1H$ NMR: ppm changes, integration changes, splitting changes, # signals
changes
CN
nitr
??

• 11.2 Practice
Draw and name the product(s) [or just assign configuration if it's a FG we haven't yet
covered] of the following reactions. Identify the nucleophile and electrophile in each
reaction. Include the mechanisms. Describe the spectroscopic changes that occur (IR
and NMRs). Assume all reactions below are SN2 (this will not remain true as you learn
more later in this chapter).
a. (S)-2-iodobutane + cyanide ion
I
b. (R)-2-bromopentane + hydroxide ion
c. (S)-2-chloropentane + an acetylide ion of your choice
0
?• Spectroscopic changes
• reactant ? product
F
• IR: what disappears in the product IR that was there in the reactant IR?
what appears in the product IR that was NOT there in the reactant IR?
• ^13C NMR: ppm changes, # peaks changes
• ^1H NMR: ppm changes, integration changes, splitting changes, # signals
changes
CN
nitr
??

Added by Robert C.

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