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Organic Chemistry

Janice Gorzynski Smith

Chapter 3

Introduction to Organic Molecules and Functional Groups - all with Video Answers

Educators

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Chapter Questions

02:50

Problem 1

What reaction occurs when CH$_3$CH$_2$OH is treated with (a) H$_2$SO$_4$? (b) NaH? What happens when CH$_3$CH$_3$ is treated with these same reagents?

Ian Kaigh
Ian Kaigh
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01:18

Problem 2

Oseltamivir can be prepared in 10 steps from shikimic acid. Identify the functional groups in oseltamivir and shikimic acid.

Chloe Schroeder
Chloe Schroeder
Numerade Educator
03:43

Problem 3

Draw the structure of a compound fitting each description:
a. an aldehyde with molecular formula C$_4$H$_8$O
b. a ketone with molecular formula C$_4$H$_8$O
c. a carboxylic acid with molecular formula C$_4$H$_8$O$_2$
d. an ester with molecular formula C$_4$H$_8$O$_2$

Ian Kaigh
Ian Kaigh
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01:03

Problem 4

Draw structures that fit each description and name the functional group in each molecule:
(a) two constitutional isomers with molecular formula C$_5$H$_{10}$O that contain different functional
groups; (b) two constitutional isomers with molecular formula C$_6$H$_{10}$O that contain the same
functional group.

Chloe Schroeder
Chloe Schroeder
Numerade Educator
04:51

Problem 5

What types of intermolecular forces are present in each compound?
a.
b.
c. (CH$_3$CH$_2)_3$N
d. CH$_2$=CHCI
e. CH$_3$CH$_2$CH$_2$COOH
f. CH$_3$-C=C-CH$_3$

Ian Kaigh
Ian Kaigh
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01:58

Problem 6

Which compound in each pair has the higher boiling point?
a. (CH$_3)_2$C = CH$_2$ or (CH$_3)_2$C = O
b. CH$_3$CH$_2$COOH or CH$_3$COOCH$_3$
c. CH$_3$(CH$_2)_4$CH$_3$ or CH$_3$(CH$_2)_5$CH$_3$
d. CH$_2$ = CHCI or CH$_2$ = CHI

Chloe Schroeder
Chloe Schroeder
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03:29

Problem 7

Explain why the boiling point of propanamide, CH$_3$CH$_2$CONH$_2$, is considerably higher than the boiling point of $N,N$-dimethylformamide, HCON(CH$_3)_2$ (213 $^\circ$C vs. 153 $^\circ$C), even though both compounds are isomeric amides.

Ian Kaigh
Ian Kaigh
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01:06

Problem 8

Predict which compound in each pair has the higher melting point.

Chloe Schroeder
Chloe Schroeder
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03:19

Problem 9

Consider acetic acid (CH$_3$CO$_2$H) and its conjugate base, sodium acetate (CH$_3$CO$_2$Na). (a) What intermolecular forces are present in each compound? (b) Explain why the melting point of sodium acetate (324 $^\circ$C) is considerably higher than the melting point of acetic acid (17 $^\circ$C).

Ian Kaigh
Ian Kaigh
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00:52

Problem 10

Which compounds are water soluble?
a. CH$_3$CH$_2$OCH$_2$CH$_3$
b. CH$_3$CH$_2$CH$_2$CH$_2$CH$_3$
c. (CH$_3$CH$_2$CH$_2$CH$_2)_3$N

Chloe Schroeder
Chloe Schroeder
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02:04

Problem 11

Label the hydrophobic and hydrophilic portions of each molecule:

Ian Kaigh
Ian Kaigh
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00:50

Problem 12

Predict the water solubility of each vitamin.

Chloe Schroeder
Chloe Schroeder
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04:41

Problem 13

(a) Identify the functional groups in the ball-and-stick model of pantothenic acid, vitamin 85. Avocados are an excellent dietary source of pantothenic acid, vitamin 85. (b) At which sites can pantothenic acid hydrogen bond to water? (c) Predict the water solubility of pantothenic acid.

Ian Kaigh
Ian Kaigh
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01:30

Problem 14

Which of the following structures represent soaps? Explain your answers.
a. CH$_3$CO$_2^-$Na$^+$
b. CH$_3$(CH$_2)_{14}$CO2$^-$Na$^+$
c. CH$_3$(CH$_2)_12$COOH
d. CH$_3$(CH$_2)_9$CO$_2{^-}$Na^+$

Chloe Schroeder
Chloe Schroeder
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03:23

Problem 15

Today, synthetic detergents like the compound drawn here, not soaps, are used to clean clothes.
Explain how this detergent cleans away dirt.

Ian Kaigh
Ian Kaigh
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00:56

Problem 16

Nonactin and valinomycin each contain only two different types of functional groups. What two
functional groups are present in nonactin? In valinomycin?

Chloe Schroeder
Chloe Schroeder
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03:21

Problem 17

Now that you have learned about solubility, explain why aspirin (Section 2.7) crosses a cell
membrane as a neutral carboxylic acid rather than an ionic conjugate base.

Ian Kaigh
Ian Kaigh
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01:51

Problem 18

Label the electrophilic and nucleophilic sites in each molecule.

Chloe Schroeder
Chloe Schroeder
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04:08

Problem 19

Considering only electron density, state whether the following reactions will occur:

Ian Kaigh
Ian Kaigh
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03:06

Problem 20

The fact that sweet-tasting carbohydrates like table sugar are also high in calories has prompted
the development of sweet, low-calorie alternatives. (a) Identify the functional groups in aspartame,
the artificial sweetener in Equal. (b) Label all of the sites that can hydrogen bond to the oxygen
atom of water. (c) Label all of the sites that can hydrogen bond with a hydrogen atom of water.

Chloe Schroeder
Chloe Schroeder
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11:01

Problem 21

(a) Identify the functional groups in the ball-and-stick model of elemicin, a compound partly responsible for the flavor and fragrance of nutmeg. (b) Draw a skeletal structure of a constitutional isomer of elemicin that should have a higher boiling point and melting point. (c) Label all electrophilic carbon atoms .

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Fortune Ononiwu
Numerade Educator
03:02

Problem 22

(a) Identify the functional groups in the ball-and-stick model of neral, a compound with a lemony odor isolated from lemon grass. (b) Draw a skeletal structure of a constitutional isomer of neral that should be more water soluble. (c) Label the most electrophilic carbon atom.

Chloe Schroeder
Chloe Schroeder
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05:15

Problem 23

Identify the functional groups in each molecule.

Ian Kaigh
Ian Kaigh
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02:59

Problem 24

Draw the seven constitutional isomers having molecular formula C$_4$H$_{10}$O. Identify the functional group in each isomer.

Chloe Schroeder
Chloe Schroeder
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01:51

Problem 25

Identify each functional group located in the following rings. Which structure represents a lactone-a cyclic ester-and which represents a lactam-a cyclic amide?

Ian Kaigh
Ian Kaigh
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03:43

Problem 26

Draw seven constitutional isomers with molecular formula C$_3$H$_6$O$_2$ that contain a carbonyl group. Identify the functional group(s) in each isomer.

Chloe Schroeder
Chloe Schroeder
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03:38

Problem 27

What types of intermolecular forces are exhibited by each compound?

Ian Kaigh
Ian Kaigh
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02:13

Problem 28

Rank the compounds in each group in order of increasing strength of intermolecular forces:
a. CH$_3$NH$_2$, CH$_3$CH$_3$, CH$_3$CI
b. CH$_3$Br, Ch$_3$I, CH$_3$Cl
c. (CH$_3)_2$C = C(CH$_3)_2$, (CH$_3)_2$CHCOOH, (CH$_3)_2$CHCOCH$_3$
d. NaCl, CH$_3$OH, CH$_3$Cl

Chloe Schroeder
Chloe Schroeder
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01:45

Problem 29

Carboxylic acids (RCOOH) can exist as dimers in some situations, with two molecules held together by two intermolecular hydrogen bonds. Show how two molecules of acetic acid (CH$_3$CO$_2$H), the carboxylic acid present in vinegar, can hydrogen bond to each other.

Ian Kaigh
Ian Kaigh
Numerade Educator
02:24

Problem 30

lntramolecular forces of attraction are often important in holding large molecules together. For example, some proteins fold into compact shapes, held together by attractive forces between nearby functional groups. A schematic of a folded protein is drawn here, with the protein backbone indicated by a blue-green ribbon, and various appendages drawn dangling from the chain. What types of intramolecular forces occur at each labeled site ($\textbf{A-F}$)?

Chloe Schroeder
Chloe Schroeder
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04:19

Problem 31

(a) Draw four compounds with molecular formula C$_6$H$_{12}$O, each containing at least one different functional group. (b) Predict which compound has the highest boiling point, and explain your reasoning.

Ian Kaigh
Ian Kaigh
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02:54

Problem 32

Rank the compounds in each group in order of increasing boiling point.
a. CH$_3$(CH$_2)_4$l, CH$_3$(CH$_2)_5$I, CH$_3$(CH$_2)_6$I
b. CH$_3$CH$_2$CH$_2$NH$_2$, (CH$_3)_3$N, CH$_3$CH$_2$CH$_2$CH$_3$
c. (CH$_3)_3$COC(CH$_3)_3$, CH$_3$(CH$_2)_3$O(CH$_2)_3$CH$_3$, CH$_3$(CH$_2)_7$OH

Chloe Schroeder
Chloe Schroeder
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03:08

Problem 33

Explain why CH$_3$CH$_2$NHCH$_3$ has a higher boiling point than (CH$_3)_3$N, even though they have the same molecular weight.

Ian Kaigh
Ian Kaigh
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00:44

Problem 34

Menthone and menthol are both isolated from mint. Explain why menthol is a solid at room temperature but menthone is a liquid.

Chloe Schroeder
Chloe Schroeder
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04:36

Problem 35

Rank the compounds in each group in order of increasing melting point.
a. (CH$_3)_2$CHOH, (CH$_3)_3$CH, (CH$_3)_2$C= O
b. CH$_3$F, CH$_3$CI, CH$_3$I

Ian Kaigh
Ian Kaigh
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01:42

Problem 36

Explain the observed trend in the melting points for four isomers of molecular formula C$_7$H$_{16}$

Chloe Schroeder
Chloe Schroeder
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03:56

Problem 37

Explain why benzene has a lower boiling point but much higher melting point than toluene.

Ian Kaigh
Ian Kaigh
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01:41

Problem 38

Rank the compounds in each group in order of increasing water solubility.
a. (CH$_3)_3$CH, CH$_3$OCH$_2$CH$_3$, CH$_3$CH$_2$CH$_2$CH$_3$, CH$_3$CH$_2$CH$_2$OH

Chloe Schroeder
Chloe Schroeder
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05:29

Problem 39

Which of the following molecules can hydrogen bond to another molecule of itself? Which can hydrogen bond with water?
a. CBr$_3$CH$_3$ c. CH$_3$OCH$_3$ e. CH$_3$CH$_2$CH$$_2$CONH$_2$ g. CH$_$3SOCH$_3$
b. CH$_3$NH$_2$ d. (CH$_3$CH$_2)_3$N f. CH$_3$CH$_2$CH$_2$CI h. CH$_3$CH$_2$COOCH$_3$

Ian Kaigh
Ian Kaigh
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00:49

Problem 40

Explain why diethyl ether (CH$_3$CH$_2$OCH$_2$CH$_3$) and 1-butanol (CH$_3$CH$_2$CH$_2$CH$_2$OH) have similar solubility properties in water, but 1-butanol has a much higher boiling point.

Chloe Schroeder
Chloe Schroeder
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03:23

Problem 41

Predict the water solubility of each of the following organic molecules:

Ian Kaigh
Ian Kaigh
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01:39

Problem 42

Predict the solubility of each of the following vitamins in water and in organic solvents:

Chloe Schroeder
Chloe Schroeder
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03:01

Problem 43

Avobenzone and dioxybenzone are two commercial sunscreens. Using the principles of solubility, predict which sunscreen is more readily washed off when an individual goes swimming. Explain your choice.

Ian Kaigh
Ian Kaigh
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01:00

Problem 44

Poly(ethylene glycol) (PEG) and poly(vinyl chloride) (PVC) are examples of polymers, large organic molecules composed of repeating smaller units covalently bonded together. Polymers have very different properties depending (in part) on their functional groups. Discuss the water solubility of each polymer and suggest why PEG is used in shampoos while PVC is used to make garden hoses and pipes. Synthetic polymers are discussed in detail in Chapters 15 and 31.

Chloe Schroeder
Chloe Schroeder
Numerade Educator
03:57

Problem 45

THC is the active component in marijuana, and ethanol is the alcohol in alcoholic beverages. Explain why drug screenings are able to detect the presence of THC but not ethanol weeks after these substances have been introduced into the body.

Ian Kaigh
Ian Kaigh
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01:19

Problem 46

Text Unavailable

Cocaine is a widely abused, addicting drug. Cocaine is usually obtained as its hydrochloride salt (cocaine hydrochloride) but can be converted to crack (the neutral molecule) by treatment with base. Which of the two compounds here has a higher boiling point? Which is more soluble in water? How does the relative solubility explain why crack is usually smoked but cocaine hydrochloride is injected directly into the bloodstream?

Chloe Schroeder
Chloe Schroeder
Numerade Educator
03:15

Problem 47

Text Unavailable

Unlike soap, which is ionic, some liquid laundry detergents are neutral molecules. Explain how each of the following molecules behaves like soap and cleans away dirt.

Ian Kaigh
Ian Kaigh
Numerade Educator
01:50

Problem 48

Many drugs are sold as their hydrochloride salts (R$_2$NH$_2{^+}$ Cl$^-$), formed by reaction of an amine (R$_2$NH) with HCI.
a. Draw the product (a hydrochloride salt) formed by reaction of acebutolol with HCI. Acebutolol is
a $\beta$ blocker used to treat
high blood pressure.
b. Discuss the solubility of acebutolol and its hydrochloride salt in water.
c. Offer a reason as to why the drug is marketed as a hydrochloride salt rather than a neutral amine.

Chloe Schroeder
Chloe Schroeder
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05:17

Problem 49

Text Unavailable

Label the electrophilic and nucleophilic sites in each molecule.

Ian Kaigh
Ian Kaigh
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05:29

Problem 50

Text Unavailable

By using only electron density arguments, determine whether the following reactions will occur:

Chloe Schroeder
Chloe Schroeder
Numerade Educator
03:05

Problem 51

Text Unavailable

The composition of a cell membrane is not uniform for all types of cells. Some cell membranes are more rigid than others. Rigidity is determined by a variety of factors, one of which is the structure of the carbon chains in the phospholipids that comprise the membrane. One example of a phospholipid was drawn in Section 3. 7 A, and another, having C-C double bonds in its carbon chains, is drawn here. Which phospholipid would be present in the more rigid cell membrane and why?

Ian Kaigh
Ian Kaigh
Numerade Educator
02:24

Problem 52

Text Unavailable

Vancomycin is a useful antibiotic for treating infections in cancer patients on chemotherapy and renal patients on dialysis. Unlike mammalian cells, bacterial cells are surrounded by a fairly rigid cell wall, which is crucial to the bacterium's survival. Vancomycin kills bacteria by interfering with their cell wall synthesis.
a. How many amide functional groups are present in vancomycin?
b. Which OH groups are bonded to $sp^3$ hybridized carbon atoms and which are bonded to $sp^2$ hybridized carbons?
c. Would you expect vancomycin to be water soluble? Explain.
d. Which proton is the most acidic?
e. Label three $different$ functional groups capable of hydrogen bonding.

Chloe Schroeder
Chloe Schroeder
Numerade Educator
03:58

Problem 53

Although diethyl ether and tetrahydrofuran are both four-carbon ethers, one compound is much more water soluble than the other. Predict which compound has higher water solubility and offer an explanation.

Ian Kaigh
Ian Kaigh
Numerade Educator
04:15

Problem 54

Answer the following questions by referring to the ball-and-stick model of fentanyl, a potent narcotic analgesic used in surgical procedures.
a. Identify the functional groups.
b. Label the most acidic proton.
c. Label the most basic atom.
d. What types of intermolecular forces are present between two molecules of fentanyl?
e. Draw an isomer predicted to have a higher boiling point.
f. Which sites in the molecule can hydrogen bond to water?
g. Label all electrophilic carbons.

Chloe Schroeder
Chloe Schroeder
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03:04

Problem 55

Explain why $\textbf{A}$ is less water soluble than $\textbf{B}$, even though both compounds have the same functional groups.

Ian Kaigh
Ian Kaigh
Numerade Educator
03:00

Problem 56

Recall from Section 1.1 OB that there is restricted rotation around carbon-carbon double bonds. Maleic acid and fumaric acid are two isomers with vastly different physical properties and p$K_a$ values for loss of both protons. Explain why each of these differences occurs.

Chloe Schroeder
Chloe Schroeder
Numerade Educator