Organic Chemistry 2nd Edition solutions

Organic Chemistry 2
Draw structures for all constitutional isomers with the followingmolecular formulas:(a) C4H10 (b) C5H12 (c) C6H14(d) C2H5Cl (e) C2H4Cl2 (f) C2H3Cl3

Organic Chemistry 2
Draw structures for all constitutional isomers with the molecular formula C4H8 that have: (a) Only single bonds (b) One double bond

Organic Chemistry 2
For each compound below, identify any polar covalent bonds and indicate the direction of the dipole moment using the symbols d+ and d-: (a) HBr (b) HCl (c) H2O (d) CH4O

Organic Chemistry 2
For each pair of compounds below, identify the one that would be expected to have more ionic character. Explain your choice. (a) NaBr or HBr (b) BrCl or FCl

Organic Chemistry 2
Draw a Lewis dot structure for each of the following compounds: (a)\( \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) (b) \(\mathrm{CH}_{3} \mathrm{CN}\) Equation Transcription: CH3CH2OH CH3CN Text Transcription: CH3CH2OH CH3CN

Organic Chemistry 2
Predict the geometry of each atom except hydrogen in the compounds below: (a) H C CC C H H H H H H H H @ (b) C C H H H H C H O H H ! (c) N C C O H H H H H H H H ! (d) C C C H H H H H H H O@

Organic Chemistry 2
Draw a Lewis structure for a compound with molecular formula C4H11N in which three of the carbon atoms are bonded to the nitrogen atom. What is the geometry of the nitrogen atom in this compound? Does this compound exhibit a molecular dipole moment? If so, indicate the direction of the dipole moment.

Organic Chemistry 2
Draw a Lewis structure of the anion AlBr4 - and determine its geometry.

Organic Chemistry 2
Draw the structure for the only constitutional isomer of cyclopropane: Cyclopropane C H H CC H H H H

Organic Chemistry 2
Determine whether each compound below exhibits a molecular dipole moment: (a) CH4 (b) NH3 (c) H2O (d) CO2 (e) CCl4 (f) CH2Br2

Organic Chemistry 2
Identify the neutral element that corresponds with each of the following electron configurations: (a) 1s 2 2s 2 2p4 (b) 1s 2 2s 2 2p5 (c) 1s 2 2s 2 2p2 (d) 1s 2 2s 2 2p3 (e) 1s 2 2s 2 2p6 3s 2 3p5

Organic Chemistry 2
In the compounds below, classify each bond as covalent, polar covalent, or ionic: (a) NaBr (b) NaOH (c) NaOCH3 (d) CH3OH (e) CH2O

Organic Chemistry 2
Draw structures for all constitutional isomers with the following molecular formulas: (a) \(\mathrm{C}_{2} \mathrm{H}_{6} \mathrm{O}\) (b) \(\mathrm{C}_{2} \mathrm{H}_{6} \mathrm{O}_{2}\) (c) \(\mathrm{C}_{2} \mathrm{H}_{4} \mathrm{Br}_{2}\)

Organic Chemistry 2
Draw structures for any five constitutional isomers with molecular formula C2H6O3.

Organic Chemistry 2
8 For each type of bond below, determine the direction of the expected dipole moment: (a) C!O (b) C!Mg (c) C!N (d) C!Li (e) C!Cl (f) C!H (g) O!H (h) N!H

Organic Chemistry 2
Predict the bond angles for all bonds in the following compounds: (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) (b) \(\mathrm{CH}_{2} \mathrm{O}\) (c) \(\mathrm{C}_{2} \mathrm{H}_{4}\) (d) \(\mathrm{C}_{2} \mathrm{H}_{2}\) (e) \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) (f) \(\mathrm{CH}_{3

Organic Chemistry 2
Identify the expected hybridization state and geometry for the central atom in each of the following compounds: (a) N H H H (b) B H H H (c) C H H H ! (d) C H H H @ (e) O H H

Organic Chemistry 2
Count the total number of s bonds and p bonds in the compound below: H H H H C C C C H H H C C N H H O

Organic Chemistry 2
For each pair of compounds below, predict which compound will have the higher boiling point and explain your choice: (a) CH3CH2CH2OCH3 or CH3CH2CH2CH2OH (b) CH3CH2CH2CH3 or CH3CH2CH2CH2CH3 (c) C C C H H H H H HO or H H C H H C H H H H

Organic Chemistry 2
Which of the following pure compounds will exhibit hydrogen bonding? (a) CH3CH2OH (b) CH2O (c) C2H4 (d) C2H2 (e) CH3OCH3 (f) CH3NH2 (g) C3H8 (h) NH3

Organic Chemistry 2
4 For each case below, identify the most likely value for x: (a) BHx (b) CHx (c) NHx (d) CH2Clx

Organic Chemistry 2
Identify the hybridization state and geometry of each carbon atom in the following compounds: (a) C H H C C H H C C C (b) C C C O H C H H H H H H H (c) C H H CC H H H H

Organic Chemistry 2
Ambien is a sedative used in the treatment of insomnia. It was discovered in 1982 and brought to market in 1992 (it takes a long time for new drugs to undergo the extensive testing required to receive approval from the Food and Drug Administration). Identify the hybridization state and geometry of ea

Organic Chemistry 2
Identify the most electronegative element in each of the following compounds: (a) CH3OCH2CH2NH2 (b) CH2ClCH2F (c) CH3Li

Organic Chemistry 2
Nicotine is an addictive substance found in tobacco. Identify the hybridization state and geometry of each of the nitrogen atoms in nicotine: N Nicotine

Organic Chemistry 2
Below is the structure of caffeine, but its lone pairs are not shown. Identify the location of all lone pairs in this compound: Caffeine N N C C N C C N O O C C H H H H H H H H H

Organic Chemistry 2
There are two different compounds with molecular formula C2H6O. One of these isomers has a much higher boiling point than the other. Explain why.

Organic Chemistry 2
1 Identify which compounds below possess a molecular dipole moment and indicate the direction of that dipole moment: (a) Cl Cl C C C C C H C H H H (b) Cl Cl C C C C C H C H H H (c) Cl Cl C C C C C H C H H H (d) Cl Br C C C C C H C H H H

Organic Chemistry 2
Methylene chloride (CH2Cl2) has fewer chlorine atoms than chloroform (CHCl3). Nevertheless, methylene chloride has a larger molecular dipole moment than chloroform. Explain.

Organic Chemistry 2
Consider the three compounds shown below and then answer the questions that follow: Compound A C H C H H H C H H C H H H N Compound B Compound C C C H H C H H C H H H N C H H H N H CC C H H H H H (a) Which two compounds are constitutional isomers? (b) Which compound contains a nitrogen atom with trig

Organic Chemistry 2
4 Propose at least two different structures for a compound with six carbon atoms that exhibits the following features: (a) All six carbon atoms are sp2 hybridized. (b) Only one carbon atom is sp hybridized, and the remaining five carbon atoms are all sp3 hybridized (remember that your compound can ha

Organic Chemistry 2
Draw all constitutional isomers with molecular formula C5H10 that possess one p bond.

Organic Chemistry 2
With current spectroscopic techniques (discussed in Chapters 1517), chemists are generally able to determine the structure of an unknown organic compound in just one day. These techniques have only been available for the last several decades. In the first half of the twentieth century, structure dete

Organic Chemistry 2
A compound with molecular formula C5H11N has no p bonds. Every carbon atom is connected to exactly two hydrogen atoms. Determine the structure of the compound.

Organic Chemistry 2
Isonitriles (A) are an important class of compounds because of the versatile reactivity of the functional group, enabling the preparation of numerous new compounds and natural products. Isonitriles can be converted to isonitrile dihalides (B), which represents a useful procedure for temporarily hidin

Organic Chemistry 2
In Section 1.12 we discussed the effect that branching can have on the boiling point of a compound. In certain instances, branching may also affect how a molecule can react with different molecules. We use the term steric hindrance to describe how branching can influence reactivity. For example, grea

Organic Chemistry 2
Epichlorohydrin (1) is an epoxide used in the production of plastic, epoxy glues, and resins (reactions of epoxides will be discussed in Chapter 14). When epichlorohydrin is treated with phenol (2), two products are formed (3 and 4). At room temperature, these liquid products are difficult to separat

Organic Chemistry 2
Consider the following table that provides bond lengths for a variety of C!X bonds (measured in ). X = F X = Cl X = Br X = I C X 1.40 1.79 1.97 2.16 C X 1.34 1.88 2.10 C X 1.27 1.63 1.79 (a) Compare the data for bonds of the type Csp3!X. Describe the trend that you observe and offer an explanation fo

Organic Chemistry 2
Positron emission tomography (PET) is a medical imaging tech nique that produces a threedimensional picture of functional processes in the body, such as the brain uptake of glucose. PET imaging requires the introduction of [18F]-fluorine (a radioactive isotope of fluorine) into molecules and can be a

Organic Chemistry 2
Phenalamide A2 belongs to a class of natural products that are of interest because of their antibiotic, antifungal, and antiviral activity. In the first total synthesis of this compound, the following boronate ester was utilized (Org. Lett. 1999, 1, 17131715): O C O C C C C C B C O C C O H3C CH3 CH3

Organic Chemistry 2
The formation of a variety of compounds called oxazolidinones is important for the synthesis of many different natural products and other compounds that have potential use as future medicines. One method for preparing oxazolidinones involves the conversion of a hydroximoyl chloride, such as compound

Organic Chemistry 2
The following compound belongs to a class of compounds, called estradiol derivatives, which show promise in the treatment of breast cancer (Tetrahedron Lett. 2001, 42, 85798582): C C C C C C C C C C C C C C C C C HO C O C C C C Cc Cb H Ca H H H H H H H H H H H H H H H H H H H H H H H H H H (a) Determ

Organic Chemistry 2
The study of analogues of small peptide chains (Chapter 25), called peptidomimetics, provides models to understand the observed stabilizing effects in larger peptides, including enzymes (natures cata lysts). The following structure shows promise for studying how enzymes coil up into very discrete sha

Organic Chemistry 2
Organic polymers (molecules with very high molecular weight) can be designed with pores (cavities) that are specifically tailored to fit a particular guest molecule due to complementary size, shape, and functional group interactions (intermolecular forces). Such systems are often inspired by binding