AP Biology - Summer Work - Chapter 4 Name MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) Organic chemistry is a science based on the study of 1) A) water and its interaction with other kinds of molecules. B) inorganic compounds. C) vital forces interacting with matter. D) functional groups. E) carbon compounds. 2) Early 19th-century scientists believed that living organisms differed from nonliving things as a result of possessing a "life force" that could create organic molecules from inorganic matter. The term given to this belief is A) organic synthesis. B) vitalism. C) mechanism. D) inorganic synthesis. E) organic evolution. 2) 3) The experimental approach taken in current biological investigations presumes that 3) A) living organisms are composed of the same elements present in nonliving things, plus a few special trace elements found only in living organisms or their products. B) living organisms can be understood in terms of the same physical and chemical laws that can be used to explain all natural phenomena. C) a life force ultimately controls the activities of living organisms and this life force cannot be studied by physical or chemical methods. D) although a life force, or vitalism, exists in living organisms, this life force cannot be studied by physical or chemical methods. E) simple organic compounds can be synthesized in the laboratory from inorganic precursors, but complex organic compounds like carbohydrates and proteins can only be synthesized by living organisms. 4) One of the following people set up a closed system to mimic Earth's early atmosphere and discharged electrical sparks through it. A variety of organic compounds common in organisms were formed. Who did this? A) Friedrich Wohler B) Hermann Kolbe C) August Kekulé D) Jakob Berzelius E) Stanley Miller 4) 1
5) Which of the following people used this apparatus to study formation of organic compounds? 5) A) Stanley Miller B) Hermann Kolbe C) August Kekulé D) Jakob Berzelius E) Friedrich Wohler 6) Which of the following people was the first to synthesize an organic compound, urea, from inorganic starting materials? A) Jakob Berzelius B) Hermann Kolbe C) August Kekulé D) Friedrich Wohler E) Stanley Miller 7) Which of the following people's synthesis of this compound from inorganic starting materials provided evidence against vitalism? 6) 7) A) August Kekulé B) Friedrich Wohler C) Stanley Miller D) Hermann Kolbe E) Jakob Berzelius 2
8) Which of the following people synthesized an organic compound, acetic acid, from inorganic substances that had been prepared directly from pure elements? A) August Kekulé B) Jakob Berzelius C) Friedrich Wohler D) Hermann Kolbe E) Stanley Miller 9) Which of the following people's synthesis of this compound from inorganic starting materials provided evidence against vitalism? 8) 9) A) Hermann Kolbe B) Stanley Miller C) August Kekulé D) Jakob Berzelius E) Friedrich Wohler 10) One of the following people was the first to suggest that organic compounds, those found in living organisms, were distinctly different from inorganic compounds found in the nonliving world. Though this suggestion is now known to be incorrect, it stimulated important research into organic compounds. Who suggested this? A) Hermann Kolbe B) Jakob Berzelius C) Stanley Miller D) Friedrich Wohler E) August Kekulé 10) 11) How many electron pairs does carbon share in order to complete its valence shell? 11) A) 2 B) 3 C) 4 D) 1 E) 8 12) A carbon atom is most likely to form what kind of bond(s) with other atoms? 12) A) covalent B) ionic C) hydrogen D) A and B only E) A, B, and C 13) Which of the following statements best describes the carbon atoms present in a seed-eating bird? 13) A) They were processed into sugars through photosynthesis. B) They are ultimately derived from carbon dioxide. C) They were incorporated into organic molecules by plants. D) Only A and C are correct. E) A, B, and C are correct. 3
14) Why are hydrocarbons insoluble in water? 14) A) The majority of their bonds are nonpolar covalent carbon-to-hydrogen linkages. B) They exhibit considerable molecular complexity and diversity. C) The majority of their bonds are polar covalent carbon-to-hydrogen linkages. D) They are hydrophilic. E) They are lighter than water. 15) How many structural isomers are possible for a substance having the molecular formula C4H10? 15) A) 2 B) 4 C) 3 D) 1 E) 11 Figure 4.1 16) The two molecules shown in Figure 4.1 are best described as 16) A) optical isomers. B) geometric isomers. C) radioactive isotopes. D) structural isomers. E) nonradioactive isotopes. Figure 4.2 17) Shown here in Figure 4.2 are the structures of glucose and fructose. These two molecules differ in the A) types of carbon, hydrogen, and oxygen atoms. B) arrangement of carbon, hydrogen, and oxygen atoms. C) number of oxygen atoms joined to carbon atoms by double covalent bonds. D) number of carbon, hydrogen, and oxygen atoms. E) answers A, B, and C 17) 4
18) Shown here in Figure 4.2 are the structures of glucose and fructose. These two molecules are 18) A) geometric isotopes. B) enantiomers. C) structural isomers. D) nonisotopic isomers. E) geometric isomers. 19) Which of the following statements correctly describes geometric isomers? 19) A) They have variations in arrangement around a double bond. B) They have the same chemical properties. C) They have an asymmetric carbon that makes them mirror images. D) Their atoms and bonds are arranged in different sequences. E) They have different molecular formulas. Figure 4.3 20) The two molecules shown in Figure 4.3 are best described as 20) A) radioactive isotopes. B) enantiomers. C) geometric isomers. D) nonisotopic isomers. E) structural isomers. 21) Research indicates that Ibuprofen, a drug used to relieve inflammation and pain, is a mixture of two enantiomers; that is, molecules that A) lack an asymmetric carbon. B) differ in the location of their double bonds. C) have identical three-dimensional shapes. D) are mirror images of one another. E) differ in their electrical charge. 22) Research indicates that Albuterol, a drug used to relax bronchial muscles, improving airflow and thus offering relief from asthma, consists only of one enantiomer, the R-form. Why is it important for this drug to consist of only one enantiomeric form, rather than a mixture of enantiomers? A) It is impossible to synthesize mixtures of enantiomers. B) Only the R-form of Albuterol has been studied; until more information is available, physicians prefer to use the pure R-form. C) Albuterol is an example of a compound for which only one enantiomer exists. D) Different enantiomers may have different or opposite physiological effects. E) It is much less expensive to synthesize one enantiomer at a time. 21) 22) 5
23) Three or four of the following illustrations depict different structural isomers of the organic compound with molecular formula C6H14. For clarity, only the carbon skeletons are shown; hydrogen atoms that would be attached to the carbons have been omitted. Which one, if any, is NOT a structural isomer of this compound? A) 23) B) C) D) E) Each of the illustrations in the other answer choices depicts a structural isomer of the compound with molecular formula C6H14. 6
24) Which of the pairs of molecular structures shown below depict enantiomers (enantiomeric forms) of the same molecule? A) 24) B) C) D) E) 7
25) Which of the pairs of molecular structures shown below do NOT depict enantiomers (enantiomeric forms) of the same molecule? A) 25) B) C) D) E) 8
26) Three or four of the pairs of structures shown below depict enantiomers (enantiomeric forms) of the same molecule. Which pair, if any, are NOT enantiomers of a single molecule? If each of the pairs depicts enantiomers, choose answer F. A) 26) B) C) D) E) F) Both illustrations in each of the other answer choices depict enantiomers of the same molecule. 27) Thalidomide and L-dopa, shown below, are examples of pharmaceutical drugs that occur as enantiomers, or molecules that 27) A) are mirror images of one another. B) lack an asymmetric carbon. C) differ in the location of their double bonds. D) differ in their electrical charge. E) have identical three-dimensional shapes. 9
28) A compound contains hydroxyl groups as its predominant functional group. Which of the following statements is true concerning this compound? A) It is hydrophobic. B) It should dissolve in a nonpolar solvent. C) It should dissolve in water. D) It lacks an asymmetric carbon, and it is probably a fat or lipid. E) It won't form hydrogen bonds with water. 28) 29) Which is the best description of a carbonyl group? 29) A) a carbon joined to two hydrogens by single covalent bonds B) a nitrogen and two hydrogens joined to a carbon by covalent bonds C) a carbon atom joined to an oxygen by a double covalent bond D) a sulfur and a hydrogen joined to a carbon by covalent bonds E) an oxygen joined to a carbon by a single covalent bond Figure 4.4 30) What is the name of the functional group shown in Figure 4.4? 30) A) hydroxyl B) aldehyde C) carbonyl D) carboxyl E) ketone 31) Which of the following contains nitrogen in addition to carbon, oxygen, and hydrogen? 31) A) an amino acid such as glycine B) a steroid such as testosterone C) an alcohol such as ethanol D) a hydrocarbon such as benzene E) a monosaccharide such as glucose 32) Which of the following is a false statement concerning amino groups? 32) A) They are basic in ph. B) They are found in amino acids. C) They are components of urea. D) They contain nitrogen. E) They are nonpolar. 33) Which two functional groups are always found in amino acids? 33) A) ketone and aldehyde B) carbonyl and carboxyl C) phosphate and sulfhydryl D) carboxyl and amino E) hydroxyl and aldehyde 34) Amino acids are acids because they always possess which functional group? 34) A) aldehyde B) carboxyl C) amino D) sulfhydryl E) carbonyl 10
35) A carbon skeleton is covalently bonded to both an amino group and a carboxyl group. When placed in water it A) would function only as a base because of the amino group. B) would function as both an acid and a base. C) would function as neither an acid nor a base. D) is impossible to determine how it would function. E) would function only as an acid because of the carboxyl group. 36) A chemist wishes to make an organic molecule less acidic. Which of the following functional groups should be added to the molecule in order to do so? A) amino B) sulfhydryl C) carboxyl D) hydroxyl E) phosphate 35) 36) 37) Which functional groups can act as acids? 37) A) carboxyl and phosphate B) ketone and amino C) carbonyl and carboxyl D) hydroxyl and aldehyde E) amine and sulfhydryl The following questions refer to the structures shown in Figure 4.5. Figure 4.5 38) Which of the structures is an impossible covalently bonded molecule? 38) A) A B) B C) C D) D E) E 39) Which of the structures contain(s) a carboxyl functional group? 39) A) A B) B C) C D) C and E E) none of the structures 40) In which of the structures are the atoms bonded by ionic bonds? 40) A) A B) B C) C D) C, D, and E only E) none of the structures 11
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question. The following questions refer to the functional groups shown in Figure 4.6. Figure 4.6 41) Which is a hydroxyl functional group? 41) 42) Which is an amino functional group? 42) 43) Which is a carbonyl functional group? 43) 44) Which is a functional group that helps stabilize proteins by forming covalent cross-links within or between protein molecules? 44) 45) Which is a carboxyl functional group? 45) 46) Which is an acidic functional group that can dissociate and release H+ into a solution? 46) 47) Which is a basic functional group that can accept H+ and become positively charged? 47) The following questions refer to the molecules shown in Figure 4.7. Figure 4.7 48) Which molecule is water soluble because it has a hydroxyl functional group? 48) 49) Which molecule is an alcohol? 49) 12
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 50) Which molecules contain a carbonyl group? 50) A) A and B B) B and C C) C and D D) D and E E) E and A SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question. 51) Which molecule has a carbonyl functional group in the form of a ketone? 51) 52) Which molecule has a carbonyl functional group in the form of an aldehyde? 52) 53) Which molecule contains a carboxyl group? 53) 54) Which molecule can increase the concentration of hydrogen ions in a solution and is therefore an organic acid? 54) The following questions refer to the molecules shown in Figure 4.8. Figure 4.8 55) Which molecule contains a sulfhydryl functional group? 55) 56) Which molecule functions to transfer energy between organic molecules? 56) 57) Which molecule contains an amino functional group, but is not an amino acid? 57) 58) Which molecule is a thiol? 58) 59) Which molecule is an organic phosphate? 59) 60) Which molecule can function as a base? 60) 13
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 61) Testosterone and estradiol are 61) A) nucleic acids. B) proteins. C) carbohydrates. D) phospholipids. E) steroids. 62) Testosterone and estradiol are male and female sex hormones, respectively, in many vertebrates. In what way(s) do these molecules differ from each other? A) Testosterone and estradiol have different functional groups attached to the same carbon skeleton. B) Testosterone and estradiol are enantiomers of the same organic molecule. C) Testosterone and estradiol are structural isomers but have the same molecular formula. D) Testosterone and estradiol are geometric isomers but have the same molecular formula. E) Testosterone and estradiol have distinctly different chemical structures, with one including four fused rings of carbon atoms, while the other has three rings. 62) 63) Organic chemistry is currently defined as 63) A) the study of hydrocarbons. B) the study of natural (as opposed to synthetic) compounds. C) the study of vital forces. D) the study of carbon compounds. E) the study of compounds made only by living cells. 64) Which of the following hydrocarbons has a double bond in its carbon skeleton? 64) A) C3H8 B) C2H4 C) CH4 D) C2H6 E) C2H2 65) Choose the term that correctly describes the relationship between these two sugar molecules: 65) A) structural isomers B) enantiomers C) geometric isomers D) isotopes SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question. 66) Identify the asymmetric carbon in this molecule: 66) 14
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 67) Which functional group is not present in this molecule? 67) A) sulfhydryl B) carboxyl C) hydroxyl D) amino 68) Which action could produce a carbonyl group? 68) A) the replacement of the nitrogen of an amine with oxygen B) the addition of a sulfhydryl to a carboxyl C) the addition of a hydroxyl to a phosphate D) the replacement of the OH of a carboxyl group with hydrogen E) the addition of a thiol to a hydroxyl 69) Which chemical group is most likely to be responsible for an organic molecule behaving as a base? 69) A) carbonyl B) hydroxyl C) amino D) carboxyl E) phosphate 15