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Exercise 2.1 | Imagine that you could distinguish between the four hydrogen atoms in a methane molecule, and labeled them H<sub>a</sub> through H<sub>d</sub>. In the images below, the <em>exact same</em> methane molecule is rotated and flipped in various positions. Draw the missing hydrogen atom labels. (It will be much easier to do ... | <img alt="E2-1S.png" class="internal" height="95px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141189/E2-1S.png?revision=1&size=bestfit&width=488&height=95" style="width: 488px; height: 95px;" width="488px"/><strong>E2.2</strong>: <em>sp</em><sup>3</sup> orbital on carbon overlapping wi... | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 1 |
Exercise 2.13 | There is a third resonance contributor for formate (which we will soon learn is considered a 'minor' contributor). Draw this resonance contributor. | <img alt="E2-13S.png" class="internal" height="96px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141170/E2-13S.png?revision=1&size=bestfit&width=106&height=96" style="width: 106px; height: 96px;" width="106px"/> | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 5 |
Exercise 3.11 | Determine the stereochemical configurations of the chiral centers in the biomolecules shown below.<img alt="From left to right: dihydroorotate molecule, mevalonate molecule, (D)-erythrose molecule." class="internal" height="197px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141240/E3-11.png?revision... | <img alt="E3-11S.png" class="internal" height="200px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141312/E3-11S.png?revision=1&size=bestfit&width=643&height=200" style="width: 643px; height: 200px;" width="643px"/><strong>E3.12</strong>: The C-O bond should be drawn as a dash to get the ... | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 8 |
Problem 1.1 | a) The structure as drawn is incomplete, because it is missing formal charges - fill them in.b) How many hydrogen atoms are on this structure?c) Identify the two important biomolecule classes (covered in section 1.3) in the structure.<img alt="P1-1.png" class="internal" height="223px" loading="lazy" src="https://chem.l... | a) Formal charges are located as shown.<img alt="P1-1aS.png" class="internal" height="222px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141155/P1-1aS.png?revision=1&size=bestfit&width=352&height=222" style="width: 352px; height: 222px;" width="352px"/>b) There are 16 hydrogen atoms:<img... | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 11 |
Problem 1.4 | <img alt="P1-4.png" class="internal" height="315px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141128/P1-4.png?revision=1&size=bestfit&width=589&height=315" style="width: 589px; height: 315px;" width="589px"/>a) What is the functional group transformation that is taking place in each re... | a)Reaction A: aldehyde to primary alcoholReaction B: Secondary alcohol to ketone; aldehyde to primary alcoholb) The second structure from the right is an appropriate abbreviation. The part of the molecule in the box does not change in the reaction, and this can be abbreviated with 'R'.<img alt="P1-4bS.png" class="inte... | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 14 |
Problem 1.6 | Note that according to VSEPR theory, ozone has bent geometry, azide ion is linear, and the geometry around the oxygen and carbon atoms of bicarbonate is bent. <img alt="P1-6S.png" class="internal" height="96px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141140/P1-6S.png?revision=1&size=bestfit&... | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 16 | |
Problem 1.8 | <img alt="P1-8.png" class="internal" height="525px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141116/P1-8.png?revision=1&size=bestfit&width=662&height=525" style="width: 662px; height: 525px;" width="662px"/>a) Fill in all missing formal charges (assume all atoms have a complete octet ... | <img alt="P1-8S.png" class="internal" height="479px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141137/P1-8S.png?revision=1&size=bestfit&width=631&height=479" style="width: 631px; height: 479px;" width="631px"/> | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 18 |
Problem 1.10 | Solutions to selected Chapter 1 problems<pclass><a href="https://chem.libretexts.org/Under_Construction/Purgatory/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)" rel="internal" title="Organic_Chemistry_With_a_Biological_Emphasis">Organic Chemistry With a Biological Emphasis </a>by <a class="link-https... | <img alt="P1-10S.png" class="internal" height="99px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141134/P1-10S.png?revision=1&size=bestfit&width=560&height=99" style="width: 560px; height: 99px;" width="560px"/>This page titled <a class="internal mt-self-link" href="https://chem.libretex... | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 20 |
Exercise 1.17 | What functional group links the phosphatidylcholine 'head' group to glycerol in the membrane lipid structure shown above?Solutions to exercises | The linking group is a phosphate diesterThis page titled <a class="internal mt-self-link" href="https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg)/01%3A_Introduction_to_Organic_Structure_and_Bonding_I/1.05%3A_Solutions_to_Chapter_1_Exercises"... | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 43 |
Exercise 2.26 | Using what you about atomic orbitals, rationalize the periodic trends in electronegativity. Why does it increase from left to right, and decrease from top to bottom? This is a good question to talk through with classmates and an instructor or tutor.Solutions to exercises | The <u>horizontal trend </u>is based on atomic number (the number of protons in the nucleus). For example, fluorine is more electronegative than carbon, because the fluorine nucleus contains three more protons, the positive charges on which pull negatively-charged electrons closer to the nucleus.The <u>vertical trend<... | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 52 |
Problem 2.1 | Example answer for bond a: "this is a <span class="mt-font-Symbol">s</span>igma bond formed by the overlap of an <em>sp<sup>3</sup></em> orbital on one carbon and an <em>sp<sup>2</sup></em> orbital on another carbon."<img alt="P2-1.png" class="internal" height="239px" loading="lazy" src="https://chem.libretexts.org/@ap... | <strong>bond a</strong> is a <span class="mt-font-Symbol">sigma</span> bond formed by the overlap of an <em>sp<sup>3</sup></em> orbital on one carbon and an <em>sp<sup>2</sup></em> orbital on another carbon.<strong>bond b</strong> is a <span class="mt-font-Symbol">s</span>igma bond formed by the overlap of an <em>sp<su... | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 55 |
Problem 2.5 | a-i) Describe the orbitals involved in the bonds indicated by the arrows, as in problem 2.1.<img alt="P2-5.png" class="internal" height="566px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141070/P2-5.png?revision=1&size=bestfit&width=717&height=566" style="width: 717px; height: 566px;" w... | <strong>bond a</strong> is a <span class="mt-font-Symbol">sigma</span> bond formed by the overlap of an <em>sp<sup>2</sup></em> orbital on one carbon and an <em>sp<sup>3 </sup></em>orbital on another carbon.<strong>bond b</strong> is a <span class="mt-font-Symbol">sigma</span> bond formed by the overlap of an <em>sp<su... | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 59 |
Problem 2.6 | a-k) For each bond indicated by an arrow, specify the types of orbitals that are overlapping (for example, overlap between two <em>sp3</em>-hybridized carbons would be denoted C<em><sub>sp3</sub></em>-C<em><sub>sp3</sub></em>)l) (functional group review) Which compound contains two aldehydes? Which contains an ether? W... | a) C<em><sub>sp3</sub></em> – O<em><sub>sp3</sub></em> b) C<em><sub>sp2</sub></em> – C<em><sub>sp3</sub></em> c) C<em><sub>sp2</sub></em> – N<em><sub>sp2</sub></em> d) C<em><sub>sp2</sub></em> – C<em><sub>sp2</sub></em> e) C<em><sub>sp3</sub></em> – C<em><sub>sp3</sub></em> f) C<e... | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 60 |
Problem 2.7 | <img alt="P2-7.png" class="internal" height="71px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141064/P2-7.png?revision=1&size=bestfit&width=235&height=71" style="width: 235px; height: 71px;" width="235px"/> | <em>shortest</em>bond e (triple bond)bond c (double bond)bond d (single bond between sp<sup>2</sup> and sp hybridized carbons)bond f (single bond between sp and sp<sup>3</sup> hybridized carbons)bond b (single bond between sp<sup>2</sup> and sp<sup>3</sup> hybridized carbons)bond a (single bond between two sp<sup>3</su... | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 61 |
Problem 2.11 | a) bonds a, b, c, and db) bonds e and f<img alt="P2-11.png" class="internal" height="287px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141059/P2-11.png?revision=1&size=bestfit&width=270&height=287" style="width: 270px; height: 287px;" width="270px"/> | <em>shortest</em>bond c (double bond)bond d (single bond between two sp<sup>2</sup> hybridized carbons)bond b (single bond between sp<sup>2</sup> and sp<sup>3</sup> hybridized carbons)bond a (single bond between two sp<sup>3</sup> hybridized carbons)<em>longest</em> | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 65 |
Problem 2.12 | The amide shown below is not capable of acting as a hydrogen bond donor (it does not have any N-H bonds), and thus is expected to be less soluble in water. The other three amides of the same formula have one or more N-H bonds, and can thus participate in hydrogen bonding with water as both donor and acceptor.<img alt="... | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 66 | |
Problem 2.13 | a) there is a separation of charge between the nitrogen indicated by the arrow and the oxygen.b) there is a separation of charge between a chlorine (positive) and one of the three nitrogens.<img alt="P2-13.png" class="internal" height="211px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141056/P2-13.... | <img alt="P2-13S.png" class="internal" height="509px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141121/P2-13S.png?revision=1&size=bestfit&width=734&height=509" style="width: 734px; height: 509px;" width="734px"/> | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 67 |
Problem 2.14 | <img alt="image160.png" class="internal" height="280px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/140269/image159.png?revision=1&size=bestfit&width=753&height=280" style="width: 753px; height: 280px;" width="753px"/><img alt="image162.png" class="internal" height="275" loading="lazy" s... | <img alt="P2-14S.png" class="internal" height="797px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141119/P2-14S.png?revision=1&size=bestfit&width=542&height=797" style="width: 542px; height: 797px;" width="542px"/> | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 68 |
Problem 2.15 | <img alt="image164.png" class="internal" height="232px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/140263/image163.png?revision=1&size=bestfit&width=214&height=232" style="width: 214px; height: 232px;" width="214px"/> | <img alt="P2-15S.png" class="internal" height="176px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141118/P2-15S.png?revision=1&size=bestfit&width=192&height=176" style="width: 192px; height: 176px;" width="192px"/> | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 69 |
Problem 2.16 | <img alt="P2-16S.png" class="internal" height="218px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141115/P2-16S.png?revision=1&size=bestfit&width=817&height=218" style="width: 817px; height: 218px;" width="817px"/> | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 70 | |
Problem 2.17 | <img alt="image166.png" class="internal" height="346px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/140259/image165.png?revision=1&size=bestfit&width=281&height=346" style="width: 281px; height: 346px;" width="281px"/> | <img alt="P2-17S.png" class="internal" height="403px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141113/P2-17S.png?revision=1&size=bestfit&width=639&height=403" style="width: 639px; height: 403px;" width="639px"/> | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 71 |
Problem 2.18 | <img alt="image168.png" class="internal" height="175px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/140255/image167.png?revision=1&size=bestfit&width=317&height=175" style="width: 317px; height: 175px;" width="317px"/>a) Several resonance contributors can be drawn in which the oxygen ato... | <img alt="P2-18S.png" class="internal" height="226px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141110/P2-18S.png?revision=1&size=bestfit&width=697&height=226" style="width: 697px; height: 226px;" width="697px"/> | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 72 |
Problem 2.19 | <img alt="P2-19.png" class="internal" height="427px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141054/P2-19.png?revision=1&size=bestfit&width=553&height=427" style="width: 553px; height: 427px;" width="553px"/> | a) 1:CH<sub>3</sub>F2: CH<sub>2</sub>F<sub>2</sub>3: CH<sub>3</sub>CHF<sub>2</sub>4: HF2 and 3 have two fluorines and are more polar than 1, so they have stronger intermolecular dipole-dipole interactions. 3 has one more carbon than 2, and therefore stronger van der Waals interactions. 4 is capable of hydrogen bonding,... | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 73 |
Problem 2.20 | <img alt="P2-20.png" class="internal" height="659px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141051/P2-20.png?revision=1&size=bestfit&width=612&height=659" style="width: 612px; height: 659px;" width="612px"/> | a) The compound on the right is more soluble (fewer hydrophobic carbons)b) The compound on the left is more soluble (ionic phosphate group)c) The compound on the left is more soluble (fewer hydrophobic carbons)d) The compound on the left is more soluble (capable of hydrogen bonding)e) The compound on the right is more ... | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 74 |
Problem 2.22 | The lone pair electrons on the peptide nitrogen are conjugated to the carbonyl <span class="mt-font-Symbol">pi </span>bond, and thus are not available to act as hydrogen bond acceptors.<img alt="P2-22S.png" class="internal" height="226px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141097/P2-22S.pn... | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 76 | |
Problem 2.27 | <img alt="P2-27.png" class="internal" height="251px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141046/P2-27.png?revision=1&size=bestfit&width=534&height=251" style="width: 534px; height: 251px;" width="534px"/> | A is <em>not</em> aromatic (sp<sup>3</sup> hybridized carbon in the ring)B is aromatic (count the lone pair and you get 10 <span class="mt-font-Symbol">pi </span>electrons, which is a Huckel number)C is <em>not</em> aromatic (the 2<em>p </em>orbital on the carbocation is empty, thus there are only four <span class="mt-... | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 80 |
Problem 2.28 | <img alt="P2-28.png" class="internal" height="257px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141044/P2-28.png?revision=1&size=bestfit&width=747&height=257" style="width: 747px; height: 257px;" width="747px"/> | <img alt="P2-28S.png" class="internal" height="214px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141091/P2-28S.png?revision=1&size=bestfit&width=751&height=214" style="width: 751px; height: 214px;" width="751px"/> | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 81 |
Problem 2.29 | <img alt="P2-29.png" class="internal" height="239px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141040/P2-29.png?revision=1&size=bestfit&width=614&height=239" style="width: 614px; height: 239px;" width="614px"/> | <img alt="P2-29S.png" class="internal" height="199px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141089/P2-29S.png?revision=1&size=bestfit&width=620&height=199" style="width: 620px; height: 199px;" width="620px"/> | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 82 |
Problem 2.30 | <img alt="P2-30.png" class="internal" height="154px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141037/P2-30.png?revision=1&size=bestfit&width=495&height=154" style="width: 495px; height: 154px;" width="495px"/>Solutions to selected problems<pclass><a href="https://chem.libretexts.org/U... | <img alt="P2-30S.png" class="internal" height="163px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141086/P2-30S.png?revision=1&size=bestfit&width=520&height=163" style="width: 520px; height: 163px;" width="520px"/>This page titled <a class="internal mt-self-link" href="https://chem.libre... | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 83 |
Exercise 3.1 | Using free rotation around C-C single bonds, show that (R,S) and (S,R)-tartaric acid are identical molecules.<img alt="soderberg 3tartartic.svg" class="internal" height="86px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/360027/soderberg_3tartartic.svg?revision=1&size=bestfit&width=332&he... | <img alt="E3-1S.png" class="internal" height="553px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141319/E3-1S.png?revision=1&size=bestfit&width=451&height=553" style="width: 451px; height: 553px;" width="451px"/> | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 90 |
Exercise 3.2 | Draw a Newman projection, looking down the C<sub>2</sub>-C<sub>3</sub> bond, of 1-butene in the conformation shown below (C<sub>2</sub> should be your <em>front</em> carbon).<img alt="image026.png" class="internal" height="91px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141184/image026.png?revisio... | <img alt="E3-2S.png" class="internal" height="172px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141318/E3-2S.png?revision=1&size=bestfit&width=369&height=172" style="width: 369px; height: 172px;" width="369px"/> | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 91 |
Exercise 1.4 | <span>Fill in all missing lone pair electrons and formal charges in the structures below. Assume that all atoms have a complete valence shell of electrons. Net charges are shown outside the brackets.</span><img alt=" " class="internal" height="296px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/14091... | <strong><img alt="E1-4 solnfig.png" class="internal" height="250px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141158/E1-4_solnfig.png?revision=1&size=bestfit&width=635&height=250" style="width: 635px; height: 250px;" width="635px"/></strong> | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 94 |
Exercise 2.30 | Rank each set of three compounds below according to their solubility in water (most soluble to least):<img alt="The compounds in set a are C5H9OHOHNH2, C6H12OHOH, and C9H18OHOH. The compounds in set b are C6H10O, C6H10OH, and C9H14O. The compounds in set c are C5H10NH, C5H11N. and C5H9NH2. " class="internal" height="37... | The main factors in these examples are the number of H-bonding groups, whether groups are H-bond acceptors <em>and</em> donors or just acceptors, and the number of carbons.<img alt="E2-30S.png" class="internal" height="406px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141133/E2-30S.png?revision=1&... | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 101 |
Exercise 2.31 | Vitamins can be classified as water-soluble or fat-soluble (consider fat to be a very non-polar 'solvent'. Decide on a classification for each of the vitamins shown below.<img alt="The vitamins are vitamin c (ascorbic acid), vitamin B3 (niacin) and vitamin A (retinol). " class="internal" height="191px" loading="lazy" s... | Ascorbic acid and niacin are water soluble (lots of hydrophilic groups relative to the number of carbons). Retinol is fat-soluble (only one hydrophilic alcohol group, a large hydrophobic hydrocarbon group. | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 102 |
Exercise 2.32 | Both aniline and phenol are mostly insoluble in pure water. Predict the solubility of these two compounds in 10% aqueous hydrochloric acid, and explain your reasoning.<img alt="Bond line drawings of aniline and phenol. " class="internal" height="141px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/140... | Aniline is basic and would be protonated (and thus cationic) in aqueous HCl. Charged species are generally water soluble. On the other hand, phenol is not basic and thus would remain as a neutral, water-insoluble molecule. | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 103 |
Exercise 2.33 | Would you predict methanol or 2-propanol (rubbing alcohol) to be a better solvent for cyclohexanone? Why?Solutions to exercises | Both alcohol solvents could form H-bonds with cyclohexanone, but isopropanol is less polar (it has three carbons), and thus would be the better solvent for the relatively nonpolar cyclohexanone. | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 104 |
Exercise 1.12 | Identify the functional groups (other than alkanes) in the following organic compounds. State whether alcohols and amines are primary, secondary, or tertiary.<img alt=" " class="internal" height="370px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141008/figE1-2-1.png?revision=1&size=bestfit&... | a) carboxylate, sulfide, aromatic, two amide groups (one of which is cyclic)b) tertiary alcohol, thioesterc) carboxylate, ketoned) ether, primary amine, alkene | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 141 |
Exercise 2.9 | Identify all conjugated and isolated double bonds in the structures below. For each conjugated pi system, specify the number of overlapping <em>p</em> orbitals, and how many pi electrons are shared among them.<img alt="Structure on the left is C10H18O. Structure on the right is C13H14O" class="internal" height="93px" l... | <img alt="E2-9S.png" class="internal" height="194px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141178/E2-9S.png?revision=1&size=bestfit&width=587&height=194" style="width: 587px; height: 194px;" width="587px"/> | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 146 |
Exercise 2.10 | Identify all isolated and conjugated double bonds in lycopene, the red-colored compound in tomatoes. How many pi electrons are contained in the conjugated pi system?<img alt="Bond line drawing of lycopene" class="internal" height="115px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/140925/figE2-2-2.p... | The conjugated system contains 22 2<em>p</em> orbitals sharing 22 <span class="mt-font-Symbol">p</span>i electrons<img alt="E2-10S.png" class="internal" height="163px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141176/E2-10S.png?revision=1&size=bestfit&width=804&height=163" style="width... | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 147 |
Exercise 1.1 | How many protons and neutrons do the following isotopes have?
<li class="lt-chem-106473"><sup>31</sup>P, the most common isotope of phosphorus</li>
<li class="lt-chem-106473"><sup>32</sup>P, a radioactive isotope of phosphorus used often in the study of DNA and RNA.</li>
<li class="lt-chem-106473"><sup>37</sup>Cl, one ... | a) The atomic number of P (phosphorus) is 15, meaning there are 15 protons. The mass number for the <sup>31</sup>P isotope is 31, so:15 protons + <strong>16 neutrons</strong> = mass number 31(recall that mass number is number of protons and neutrons).<em>(for parts b-d, use the same reasoning as above)</em>b) 15 prot... | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 153 |
Exercise 1.2 | The electron configuration of a carbon atom is 1s<sup>2</sup>2s<sup>2</sup>2p<sup>2</sup>, and that of a sodium cation (Na<sup>+</sup>) is 1s<sup>2</sup>2s<sup>2</sup>2p<sup>6</sup>. Show the electron configuration for:
<li class="lt-chem-106473">a nitrogen atom</li>
<li class="lt-chem-106473">an oxygen atom</li>
<li c... | a) 1<em>s</em><sup>2</sup>2<em>s</em><sup>2</sup>2<em>p</em><sup>3</sup> b) 1<em>s</em><sup>2</sup>2<em>s</em><sup>2</sup>2<em>p</em><sup>4</sup> c) 1<em>s</em><sup>2</sup>2s<sup>2</sup>2<em>p</em><sup>5</sup>d) 1<em>s</em><sup>2</sup>2s<sup>2</sup>2<em>p</em><sup>6</sup>3<em>s</em><sup>2</sup> e) 1<em>s</em><sup>2</su... | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 154 |
Exercise 1.3 | Draw Lewis structures for the following species (use lines to denote bonds, dots for lone-pair electrons). All atoms should have a complete valence shell of electrons.
<li class="lt-chem-106473">ammonia, NH<sub>3</sub></li>
<li class="lt-chem-106473">ammonium ion, NH<sub>4</sub><sup>+</sup></li>
<li class="lt-chem-1064... | <img alt="E1.3S.png" class="internal" height="616px" loading="lazy" src="https://chem.libretexts.org/@api/deki/files/141175/E1.3S.png?revision=1&size=bestfit&width=582&height=616" style="width: 582px; height: 616px;" width="582px"/> | https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg) | 155 |
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