Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Problem 2.3
For each compound below, identify the most reactive pair of electrons (either a bond
or a lone pair) and specify the corresponding type of frontier orbital (namely n, t
or ơ).
NH2
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Transcribed Image Text:Problem 2.3 For each compound below, identify the most reactive pair of electrons (either a bond or a lone pair) and specify the corresponding type of frontier orbital (namely n, t or ơ). NH2
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  • Below is the SN2 reaction between iodocyclohexane and cyanide (CN–). Draw the missing curved arrow notation in the first box to reflect electron movements. In both boxes, add lone pairs of electrons and nonzero formal charges.
    Problem (#2.) For each ion below, draw all reasonable resonance structures (linked by resonance arrows “↔”). Include curved arrows that indicate the movement of electrons between each resonance structure. Assign non-zero formal charges to each atom for each resonance structure. (a.) NO3–  (nitrate) (b.) CH3COO– (acetate) (c.) N3– (azide) (d.) NCO– (isocyanate) Problem (#3.) For each ion in question 2, draw a resonance hybrid, assigning non-zero formal and/or partial charges (δ+, δ–) as needed. Problem (#4.) For each skeletal structure below, satisfy the valences (or octets) of all of the atoms by filling in double and triple bonds as well as unshared electron pairs. Assign non-zero formal charges and show the overall charge if the structure is an ion. See photo attached for Problem number 4.   Problem (#5.) For each structure in question 4, draw a resonance hybrid (if it has one) and assign non-zero formal and/or partial charges as needed.
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