Schaum's Outline of Organic Chemistry

George Hademenos, George Hademenos

Chapter 2 BONDING AND MOLECULAR STRUCTURE - all with Video Answers

Educators

Chapter Questions

03:25

Problem 1

Show the distribution of electrons in the atomic orbitals of $(a)$ carbon and $(b)$ oxygen.

Shahina -

Numerade Educator

01:15

Problem 2

What type of $\mathrm{MO}$ results from side-to-side overlap of an $s$ and a $p$ orbital?

Sima Sarker

Numerade Educator

02:25

Problem 3

List the differences between a $\sigma$ bond and a $\pi$ bond.

Lottie Adams

Numerade Educator

03:11

Problem 4

Show the electron distribution in MO's of $($ a $) \mathrm{H}_2$, (b) $\mathrm{H}_2^{+}$, (c) $\mathrm{H}_2^{-},($d $) \mathrm{He}_2$. Predict which are unstable.

Adriano Chikande

Numerade Educator

00:35

Problem 5

Since the $\sigma$ MO formed from $2 s$ AO's has a higher energy than the $\sigma^*$ MO formed from is AO's, predict whether $(a) \mathrm{Li}_2,(b) \mathrm{Be}_2$ can exist.

Hunza Gilgit

Numerade Educator

04:21

The MO's formed when the two sets of the three $2 p$ orbitals overlap are
$$
\pi_{2 p_1} \pi_{2 p_z} \sigma_{2 p_{\mathrm{s}}} \pi_{2 p_r}^* \pi_{2 p_z}^* \sigma_{2 p_1}^*
$$
(the $\pi$ and $\pi^*$ pairs are degenerate). (a) Show how MO theory predicts the paramagnetism of $\mathrm{O}_2$. (b) What is the bond order in $\mathrm{O}_2$ ?

Adriano Chikande

Numerade Educator

01:18

Problem 7

The $\mathrm{H}_2 \mathrm{O}$ molecule has a bond angle of 105 . (a) What type of $\mathrm{AO}$ 's does $\mathrm{O}$ use to form the two equivalent $\sigma$ bonds with $\mathrm{H}$ ? $(b)$ Why is this bond angle less than $109.5^{\circ}$ ?

Meera Devi

Numerade Educator

01:25

Problem 8

Each $\mathrm{H}-\mathrm{N}-\mathrm{H}$ bond angle in : $\mathrm{NH}_3$ is $107^{\circ}$. What type of $\mathrm{AO}$ 's does $\mathrm{N}$ use?

David Collins

Numerade Educator

02:17

Problem 9

Predict the shape of $(a)$ the boron trifluoride molecule $\left(\mathrm{BF}_3\right)$ and $(b)$ the boron tetrafluoride anion $\left(\mathrm{BF}_4^{-}\right)$. All bonds are equivalent.

Arpit Gupta

Numerade Educator

02:28

Problem 10

Arrange the $s, p$, and the three $s p$-type $\mathrm{HO}$ 's in order of decreasing energy.

Katherine Mccandless

Numerade Educator

01:07

Problem 11

What effect does hybridization have on the stability of bonds?

Joshua Speer

Numerade Educator

01:51

Problem 12

Use the HON method to determine the hybridized state of the underlined elements:
(a) $\mathrm{CHCl}_3$
(b) $\mathrm{H}_2 \mathrm{C}=\mathrm{CH}_2$
(c) $\mathrm{O}=\mathrm{C}=\mathrm{O}$
(d) $\mathrm{HC}=\mathrm{N}:(e) \mathrm{H}_3 \underline{\mathrm{O}}^{+}$

Lijeesh Krishnan

Numerade Educator

01:05

Problem 13

What do the molecular dipole moments $\mu=0$ for $\mathrm{CO}_2$ and $\mu=1.84 \mathrm{D}_{\text {for }} \mathrm{H}_2 \mathrm{O}$ tell you about the shapes of these molecules?

Lottie Adams

Numerade Educator

04:32

Problem 14

Determine the oxidation number of each $\mathrm{C}$. $(\mathrm{ON})_{\mathrm{C}}$, in: (a) $\mathrm{CH}_{4 \cdot} \cdot(b)\left(\mathrm{H}_3 \mathrm{OH},(c) \mathrm{CH}_3 \mathrm{NH}_2,(d)\right.$ $\mathrm{H}_2 \mathrm{C}=\mathrm{CH}_2$. Use the data $(\mathrm{ON})_N=-3 ;(\mathrm{ON})_{11}=1 ;(\mathrm{ON})_0=-2$.

Jacob Light

Numerade Educator

03:28

Problem 15

Account for the following progressions in boiling point
(a) $\mathrm{CH}_4,-161.5^{\circ} \mathrm{C}, \mathrm{Cl}_2,-34^{\circ} \mathrm{C}$;$\mathrm{CH}_3 \mathrm{Cl} .-24^{\circ} \mathrm{C}$. (b) $\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{OH} .78 \mathrm{C}: \mathrm{CH}_3 \mathrm{ClI}_2 \mathrm{~F}, 46 \mathrm{C} ; \mathrm{CH}_1 \mathrm{CH}_2 \mathrm{CH}_3,-42^{\circ} \mathrm{C}$.

Kendrick Buford

Numerade Educator

00:36

Problem 16

The boiling points of $n$-pentane and its isomer neopentane are $36.2^{\circ} \mathrm{C}$ and $9.5^{\circ} \mathrm{C}$, respectively. Account for this difference (see Problem 1.4 for the structural formulas.)

Matthew Confer

Numerade Educator

02:56

Problem 17

Classify the following solvents: $(a)\left(\mathrm{CH}_3\right)_2 \mathrm{~S}=\mathrm{O}$, dimethyl sulfoxide; (b) $\mathrm{CCl}_4$, carbon tetrachloride; (c) $\mathrm{C}_6 \mathrm{H}_6$, benzene; (d) $\mathrm{HCN}\left(\mathrm{CH}_3\right)_2$ Dimethylformamide; $(e) \mathrm{CH}_3 \mathrm{OH}$, methanol; $(f)$ liquid $\mathrm{NH}_3$.

Anish Wadhwa

Numerade Educator

01:10

Problem 18

Mineral oil, a mixture of high-molecular-weight hydrocarbons, dissolves in $n$-hexane but not in water or ethyl alcohol, $\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{OH}$. Explain.

Will Li

Numerade Educator

02:54

Problem 19

Explain why $\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{OH}$ is much more soluble in water than is $\mathrm{CH}_3\left(\mathrm{CH}_2\right)_3 \mathrm{CH}_2 \mathrm{OH}$.

Nicholas Sacco

Numerade Educator

00:37

Problem 20

Explain why $\mathrm{NaCl}$ dissolves in water.

Nicole Mabante

Numerade Educator

09:37

Problem 21

Compare the ways in which $\mathrm{NaCl}$ dissolves in water and in dimethyl sulfoxide.

Shalini Tyagi

Numerade Educator

01:54

Problem 22

Write contributing structures, showing formal charges when necessary, for $(a)$ ozone, $\mathrm{O}_3 ;$ ( $\left.b\right) \mathrm{CO}_2$; (c) hydrazoic acid, $\mathrm{HN}_3 ;($ d $)$ isocyanic acid, $\mathrm{HNCO}$. Indicate the most and least stable structures and give reasons for your choices. Give the structure of the hybrid.

Lottie Adams

Numerade Educator

04:07

Problem 23

(a) Write contributing structures and the delocalized structure for (i) $\mathrm{NO}_2^{-}$and (ii) $\mathrm{NO}_3^{-}$. (b) Use $p$ AO's to draw a structure showing the delocalization of the $p$ electrons in an extended $\pi$ bond for (i) and (ii). (c) Compare the stability of the hybrids of each.

Eugene Schneider

University of Minnesota - Twin Cities

03:24

Problem 24

Indicate which one of the following pairs of resonance structures is the less stable and is an unlikely contributing structure. Give reasons in each case.
(Figure can't copy)

Bobby Barnes

University of North Texas

01:07

Problem 25

Distinguish between an $\mathrm{AO}$, an $\mathrm{HO}$, an $\mathrm{MO}$ and a localized $\mathrm{MO}$.

Mayukh Banik

Numerade Educator

01:10

Problem 26

Show the orbital population of electrons for unbonded $\mathrm{N}$ in $(a)$ ground state, (b) $s p^3,(c) s p^2$, and $(d)$ $s p$ hybrid states.

Lottie Adams

Numerade Educator

07:29

Problem 27

(a) $\mathrm{NO}_2^{+}$is linear, (b) $\mathrm{NO}_2^{-}$is bent. Explain in terms of the hybrid orbitals used by $\mathrm{N}$.

Luz Esteban-Torres

Numerade Educator

07:23

Problem 28

Draw an orbital representation of the cyanide ion, $: \mathrm{C} \equiv \mathrm{N}:^{-}$.

Rashmi Sinha

Numerade Educator

08:05

Problem 29

(a) Which of the following molecules possess polar bonds: $\mathrm{F}_2, \mathrm{HF}, \mathrm{BrCl}, \mathrm{CH}_4, \mathrm{CHCl}_3, \mathrm{CH}_3 \mathrm{OH}$ ?
(b) Which are polar molecules?

Colton Brushwood

Numerade Educator

03:55

Problem 30

Considering the difference in electronegativity between $\mathrm{O}$ and $\mathrm{S}$, would $\mathrm{H}_2 \mathrm{O}$ or $\mathrm{H}_2 \mathrm{~S}$ exhibit greater (a) dipole-dipole attraction, (b) H-bonding?

Arpit Gupta

Numerade Educator

02:07

Problem 31

Nitrogen trifluoride $\left(\mathrm{NF}_3\right)$ and ammonia $\left(\mathrm{NH}_3\right)$ have an electron pair at the fourth corner of a tetrahedron and have similar electronegativity diffrences between the elements $(1.0$ for $\mathrm{N}$ and $\mathrm{F}$ and 0.9 for $\mathrm{N}$ and $\mathrm{H})$. Explain the larger dipole moment of ammonia $(1.46 \mathrm{D})$ as compared with that of $\mathrm{NF}_3(0.24 \mathrm{D})$.

David Collins

Numerade Educator

02:58

Problem 32

$\mathrm{NH}_4^{+}$salts are much more soluble in water than are the corresponding $\mathrm{Na}^{+}$salts. Explain.

Eileen Sullivan

Numerade Educator

01:42

Problem 33

The $\mathrm{F}^{-}$of dissolved $\mathrm{NaF}$ is more reactive in dimethyl sulfoxide,
(Figure can't copy)
and in acetonitrile, $\mathrm{CH}_3 \mathrm{C}=\mathrm{N}$, than in $\mathrm{CH}_3 \mathrm{OH}$. Explain.

Arun Bana

Numerade Educator

01:32

Problem 34

Find the oxidation of the $\mathrm{C}$ in (a) $\mathrm{CH}_3 \mathrm{Cl}$, (b) $\mathrm{CH}_2 \mathrm{Cl}_2 \cdot\left(\right.$ c) $\mathrm{H}_2 \mathrm{CO}$, (d) $\mathrm{HCOOH}$, and (e) $\mathrm{CO}_2$, if $(O N)_{\mathrm{C} 1}=-1$

Amy Jiang

Numerade Educator

11:29

Problem 35

Give a True or False answer to each question and justify your answer. (a) Since in polyatomic anions $\mathrm{XY}_m^{n-}$ (such as $\mathrm{SO}_4^{2-}$ and $\mathrm{BF}_4^{-}$), the central atom $\mathrm{X}$ is usually less electronegative than the peripheral atom $\mathrm{Y}$, it tends to acquire a positive oxidation number. (b) Oxidation numbers tend to be smaller values than formal charges. (c) A bond between dissimilar atoms always leads to nonzero oxidation numbers. (d) Fluorine never has a positive oxidation number.

Vishal Sharma

Numerade Educator

01:50

Problem 36

Which of the following transformations of organic compounds are oxidations, which are reductions, and which are neither?
(a) $\mathrm{H}_2 \mathrm{C}=\mathrm{CH}_2 \longrightarrow \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{OH}$
(b) $\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{OH} \longrightarrow \mathrm{CH}_3 \mathrm{CH}=\mathrm{O}$
(c) $\mathrm{CH}_3 \mathrm{CHO} \longrightarrow \mathrm{CH}_3 \mathrm{COOH}$
(d) $\mathrm{H}_2 \mathrm{C}=\mathrm{CH}_2 \longrightarrow \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{Cl}$
(e) $\mathrm{HC}=\mathrm{CH} \longrightarrow \mathrm{H}_2 \mathrm{C}=\mathrm{CH}_2$

John Nicolle

Numerade Educator

01:33

Problem 37

Irradiation with ultraviolet (uv) light permits rotation about a $\pi$ bond. Explain in terms of bonding and antibonding MO's

Lottie Adams

Numerade Educator

02:40

Problem 38

Write the contributing resonance structures and the delocalized hybrid for (a) $\mathrm{BCl}_3,\left(\right.$ b) $\mathrm{H}_2 \mathrm{CN}_2$ (diazomethane).

Lottie Adams

Numerade Educator

04:23

Problem 39

Arrange the contributing structures for $(a)$ vinyl chloride, $\mathrm{H}_2 \mathrm{C}=\mathrm{CHCl}$, and $(b)$ formic acid, $\mathrm{HCOOH}$, in order of increasing importance (increasing stability) by assigning numbers starting with 1 for most important and stable.

Anupa Sharad Medhekar

Numerade Educator

01:38

Problem 40

What is the difference between isomers and contributing resonance structures?

Xinran Wang

Numerade Educator

01:51

Problem 41

Use the HON method to determine the hybridized state of the underlined elements:
(a) $\mathrm{HC}=\mathrm{CH}$
(b) $\mathrm{H}_2 \mathrm{C}=\mathrm{O}$
(c) $\mathrm{HC}=\mathrm{C}^{-}$
(d) $\mathrm{AlCl}_6^{3-}$
(e) $\mathrm{PF}_5$
(f) $\mathrm{CH}_3 \mathrm{O} \mathrm{CH}_3$

Lijeesh Krishnan

Numerade Educator

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