Problem

(a) Compare the bond enthalpies (Table) of the carbon– carbon single, double, and triple b...

(a) Compare the bond enthalpies (Table) of the carbon– carbon single, double, and triple bonds to deduce an average π-bond contribution to the enthalpy. What fraction of a single bond does this quantity represent?

Table Average Bond Enthalpies(kJ/mol)

Single Bonds

C—H

413

N—H

391

463

O—H

F—F

155

C—C

348

N—N

163

O—O

146

 

 

C—N

293

N—O

201

O—F

190

Cl—F

253

C—O

358

N—F

272

O—Cl

203

Cl—Cl

242

C—F

485

N—Cl

200

O—l

234

 

 

C—Cl

328

N—Br

243

 

 

Br—F

237

C—Br

276

 

 

S—H

339

Br—Cl

218

C—l

240

H—H

436

S—F

327

Br—Br

193

C—S

259

H—F

567

S—Cl

253

 

 

 

 

H—Cl

431

S—Br

218

I—Cl

208

Si—H

323

H—Br

366

S—S

266

I—Br

175

Si—Si

226

H—l

299

 

 

I—l

151

Si—C

301

 

 

 

 

 

 

Si—O

368

 

 

 

 

 

 

Si—Cl

464

 

 

 

 

 

 

Multiple Bonds

C═C

614

N═N

418

O═O

495

 

 

C≡C

839

N≡N

941

 

 

 

 

C═N

615

N═O

607

S═O

523

 

 

C≡N

891

 

 

S═S

418

 

 

C═O

799

 

 

 

 

 

 

C≡O

1072

 

 

 

 

 

 

, (b) Make a similar comparison of nitrogen–nitrogen bonds. What do you observe? (c) Write Lewis structures of N2H4, N2H2, and N2, and determine the hybridization around nitrogen in each case., (d) Propose a reason for the large difference in your observations of parts (a) and (b).

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