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109AExam1 - cl 1 5 minutes 10 oints Give a structure for...

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Unformatted text preview: cl 1. 5 minutes 10 oints Give a structure for each of the following. a. sec—butyl alcohol 011391405014, 0/4 b. the conjugate acid of acetic acid +0 14 I! afi/C\ OH "“c; a tertiary amine ’ (7, d. a tertiary alcohol fl, (Z'—c’l;~0/4 (z, e. a compound with molecular formula CSH12 that has one tertiary carbon 0359+ cg Q2 61/; 8' 2. 16 minutes, 14 points) Answer the following: a. What is the H—C—H bond angle in HZC =0 ? #280 + e b. What is the C—N-C bond angle in (CH3)2NHZ ? /09-§ c. Draw the two chair conformers of cis-l q4—dimethylcyclohexane % a d. The most stable conformation of 3-methylpentane Viewed along the C—2 —C—3 bond. 0% 1+ mg 9%» or; C64 Maui} “is H- 05003 c. Which of the following has cis—trans isomers? 2—methyl-2-hexene 4-methyl-2-hexene d. What is the hybridization of the carbon atom in the methyl carbocation? 57; e. A compound has a Ka = 8.7 X 10'4. What is its approximate pKa value? between 2-3 between 3—4 between 4—5 between 5-6 between 6-7 between 7-8 7 3. (6 minutes, 12 points) Answer the following: a. Draw a Lewis structure for the following: Hco; §: 23: meg: 0: §: 61 Mid-— c—{afi‘ b. Draw the most stable conformer of cistléethyl-Z-methylcyclohexane 3 H- /%U‘b H c. What kind of orbitals does boron use to form the three identical bonds in BH3? (hint: the atomic number of boron is 5). L 5P d. Magnesium has an atomic number of 12. Which would you expect to be more stable, Mg+ 0' e. Does the following compound have the E or the Z configuration? CH3 I CH3 CHCH2 \ [CHZOH [C =C\ CH3 CH CH2CH2B1' (le3 g f. Which of the indicated bonds is longer? 5L 4. 2 minutes 8 oints Which of the following compounds is a stronger acid? a. or HF ‘31 i? b. BrCHZCOH 01' ClCHZCOH ‘3' c. or ClCHZCOH ‘3: d. or CH3 CCHZOH 5. 12 minutes, 6 points) 3 Give a structure for each of the following. a. At What pH will the concentration of a compound with a pKa of 8.4 be 100 times greater in its basic form than in its acidic form? M91 b. ally] bromide (45 = 54.5134; fir— c/éEA (Le—l,I 0 cu zap/91 01$ c. isobutyl vinyl ether [ll 6. 18 minutes, 12 points) Answer the following: a. Which of the following is an appropriate name? ( 5—bromo-2-pentene) 5—chloro—3—hexene 2—Vinylpentane 5-ethylcyclohexene 2-ethyl-2—butene b" Which of the following would have the most negative change in entropy? A --> B + C 2A -—> B + C A + B --> C + D A --> 2B c. Which would yield the most favorable (most negative)A G°? negative H and positive S at a low temperature negative H and negative S at a high temperature positive H and positive S at a low temperature positive H and negative S at a low temperature negative H and positive S at a high temperature d. Which of the following are NOT two appropriate names for the same compound? vinyl chloride and chloroethene propene and propylene isobutylene and 2-methylpropene ethene and ethylene e. Which of the following describes a reaction with a negative A G°? The reaction occurs rapidly. The products are less stable than the reactants." ’ ” T The reaction is endergonic. The reaction is exothermic. he products are more stable than the reactan .. f. Which of the following is not a nucleophile? Br: ethene ammonia BH3 water E 7. 14 minutes, 11 points) Answer the following: a. Write the acid—base reaction that occurs when methylamine is added to water. 03/0/12 ,L ago (:2. Crab/13g} + #o‘ b. Does the reaction [email protected] products? c. The following compounds are shown in their acid forms. Draw the form in which each will predominate at pH: 7. O M “CHgCHiCHg-OHV .. 'CHgC’HécHZiTIHg I” I 6H3CH2gOH 7 agcgcg, 0%! ages; cg A3215 uécggo‘ (1. Which is the strongest base? if CH30_ CH3NH2 CHSOH CH3NH CH3co‘ e. Which is the weakest base? _ — || _ CHSO CH3NH2 CH3OH CH3NH CH3CO v“ g. g. (3 minutes, 9 points) \ \ Answer the following: a. In which solvent would cyclohexane have the lowest solubility, diethyl ether(@ or hexane? b. Which compound has a higher boiling point, @r 1methoxypentane? c. Which compound has a higher boiling point, @r ethylmethylamine? d. Which compound has a greater dipole moment, CC14 [email protected] e. Which compound is more soluble in water, 1—butanol o 1-propanol " f. m1. co‘mpmd mangle. boring psinuriscpemanei ‘ *‘ g. Which compound has a shorter carbon-carbon bond, CH2=CH2 0- h. What has a greater dipole moment,- or trans—Z—butene? i. Which compound has a higher boiling point, diethyl ether or 9. (6 minutes, 10 points) Name each of the following: a. b. CHZCHg | . CH CHCHCH Cl 5214mm.- 5 —W 3 I 2 / W Cl CH3CIJHCHZCIJIZCI:HCHZCH2CH3 7— W64 0 6.74244 r? CH3 OH Br Br CHSCHZ 4—W — fixing/— J”%‘Z’W CH3 e. CH3CH2C|HCH2CHZCIZHCH3 4 _ W fl/V‘W‘Z £77; . - _ 2 NHCH3 Br ll 10. 18 minutes, 12 points) Answer the following: a. Which of the following is not a true statement concerning bonds formed by sps, sp2, and Sp hybridized orbitals? The more s character, the stronger the bond. The more 3 character, the larger the bond angle. The more s character, the shorter the bond. An SP2 orbital has more 5 character than an Sp3 orbital. The more 5 character, the smaller the bond ang e. I wewmb.~W—hichwof~therf~ollowingncompoundsvi-senot~a~trans—(ii-substitutedrseyeloliex-ane? v ~A 1,4-disubstituted: one axial and one equatorial substituen 1,3—disubstituted: one axial and one equatorial substituent 1,4—disubstituted: two equatorial substituents 1,3-disubstituted: one axial and one equatorial substituent 1,4—disubstituted: two axial substituents c. What is the common name of N—methyl—l-propanamine? butylamine girepylmethylamine > methylpropylamine dimethylethylamine diethylamine d. What is the general molecular formula of an acyclic (noncyclic) hydrocarbon with three double bonds? CnHZn—l CnHZn—S CnHZn—S CnHZn—Z e. Which statement is NOT correct? The methyl groups in (E)-3-methyl—2—pentene are on the same side of the double bond. W (Z)=2—methyl—2—penteneisal‘socalled~~ciSrlrpentene -- ~ ~ , (E)-2—butene can be called trans—2—butene. (E)-2—pentene can be called trans—Z—pentene. (Z)—4—methyl—2—pentene can be called cis—4—methyl—2—pentene. f. How many transition states and intermediates does a 3—step reaction have? 2 transition states and 3 intermediates 3 transition states and 3 intermediates 2 transition states and 2 intermediates 3 transition states and O intermediates 3 transition states and 2 intermedia ...
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