CHEM 3331 1nd EditionExam # 1 Study Guide Lectures: 1 - 8Lecture 1 & 2 (August 25 & 27)Chapter 11. Name each element that corresponds to each electronic configuration.a) 1s2 2s2 2p2 b) 1s2 2s2 2p4 c) 1s2 2s2 2p6 3s2 3p3 d) 1s2 2s2 2p6 3s2 3p52. State whether bonding is ionic, covalent, or both.a) NaCl b) NaOH c)CH3Li d)CH2Cl2 e) NaOCH3 f) HCO2Na g)CF43. Draw lewis structures for each.a) N2H4 b) N2H2 c) (CH3)2NH2Cl d)CH3CN e)CH3CHO f)CH3S(O)CH3g) H2SO4 h) CH3NCO i) CH3OSO2CH3 j) CH3C(NH)CH3 k) (CH3)3CNO4. Show the direction of the dipole moments.a) C-Cl b) C-H c) C-Li d) C-N e) C-O f) C-B g) C-Mg h) N-Hi) O-H j) C-Br5. rank in order of increasing acidity.HF, NH3, H2SO4, CH3OH, CH3COOH, H3O+, H2OLecture 3 & 4 (September 3 & 8)Chapter 21. give the definition and an example for each class of organic compounds.a) Alkane b) Alkene c) Alkyne d) Alcohol e) Ether f) Ketone g) Aldehydeh) Aromatic Hydrocarbon i) Carboxylic Acid j) Ester k) Amine l) Amidem) nitrile2. give the hybridization and bond angles around each atom except for hydrogen.a) H3O+ b) –OH c) CH2CHCN d) (CH3)3N e) [CH3NH3]+ f) CH3COOHg) CH3CHNH h) CH3OH i) CH2O3. Which of the following can form hydrogen bonds? Which can form hydrogen bonds with water? Which can you expect to be soluble in water?a) (CH3CH2)2NH b) (CH3CH2)3N c) H3CH2CH2OH d) (CH3CH2CH2)2Oe) CH3(CH2)3CH3 f) CH2=CH-CH2CH3 g) CH3COCH3 h) CH3CH2COOHi) CH3CH2CHO4. which compound of the pair has the highest boiling point?a) CH3CH2OCH3 or CH3CH(OH)CH3b) CH3CH2CH2CH3 or CH3CH2CH2CH2CH3c) CH3CH2CH2CH2CH3 or (CH3)2CHCH2CH3d) CH3CH2CH2CH2CH3 or CH3CH2CH2CH2CH2Cl5. identify the functional groups in the following compounds.a) penicillin G b) dopamine c) capsaicin d) thyroxine e) testosteroneLecture 5 & 6 (September 10 & 15)Chapter 31. draw the structure that corresponds with each namea) 3-ethyloctane b) 4-isopropyldecane c) sec-butylcycloheptaned) 2,3- dimethyl-4-propylnonane e) 2,2,4,4-tetramethylhexanef) trans-1,3-diethylcyclopentane g) cis-1-ethyl-4-methylcyclohexaneh) isobutylcyclopentane i) tert-butylcyclohexane j) pentylcyclohexanek) cyclobutylcyclohexane l) cis-1-bromo-3-chlorocyclohexane2. write structures for a homologous series of alcohols having from 1 to 6 carbons.3. Draw each structure and name it correctly.a) 2-ethylpentane b) 3-isopropylhexane c) 5-chloro-4-methylhexaned) 2-dimethylbutane e) 2-cyclohexylbutane f) 2,3-diethylcyclopentane4. which compound has a higher boiling point?a) octane or 2,2,3-trimethylpentaneb) nonane or 2-methylheptanec) 2,2,5-trimethylhexane or nonane5. draw two chair conformations of each compound. Label substituents as axial and equatorial. Which is more stable?a) cis-1-ethyl-2-isopropylcyclohexane b) trans-1-ethyl-2-isopropylcyclohexanec) cis-1-ethyl-3-methylcyclohexane d) trans-1-ethyl-3-methylcyclohexanee) cis-1-ethyl-4-methylcyclohexane f) trans-1-ethyl-4-methylcyclohexane6. convert each Newman projection to an equivalent line-angle formula and assign IUPAC namea) b) c)d) e) f) g) h) i)j) Lecture 7 & 8 (September 17 & 22)Chapter 41. draw a reaction-energy diagram for a one-step exothermic reaction and label all the parts.2. use bond dissociation enthalpies to calculate ΔH˚.a)CH3-CH3 + I2  CH3CH2I + HIb) CH3CH2Cl + HI  CH3CH2I + HClc) (CH3)3C-OH +HCl  (CH3)3C-Cl + H2Od) CH3CH2CH3 + H2  CH3CH3 +CH4e) CH3CH2OH + HBr  CH3CH2-Br + H2O3.a) draw the structure for the transition state for the second propagation step in chlorination of methane:˚CH3 + Cl2  CH3Cl + Cl˚b) repeat this for the second propagation step in bromination of methane. 4. propose a mechanism and calculate ΔH for each step proposed. Knowing:Cyclopentane + CI4  (H2O2 and heat) 1-iodocyclopentane + HCI3I3C-I=45 kcal/mol HO-I= 56 kcal/mol I3C-H= 100 kcal/molHO-OH= 51 kcal/mol 1-hydrocyclopentane= 95 kcal/mol 1-iodocyclopentane= 53 kcal/molAnswersChapter 11. a) carbon b) oxygen c) phosphorus d) chlorine2. a) ionic b) covalent (H-O-) ionic (Na+ OH-) c) covalent (H-C and C-Li) C-Li is strongly polarized d) covalent e) covalent (H-C and C-O) ionic (Na+ OCH3-)f) covalent (H-C, C=O, and C-O-) and ionic (HCO2- Na+) g) covalent3. a) b) c) d) e) f)g) h)i) j)k)4. arrow points in direction of negative polarity a) C-Cl  b) C-H  c) C-Li d) C-N  e) C-O  f) C-B  g) C-Mg  h) N-H  i) O-H j) C-Br 5. NH3< H2O~CH3OH< CH3COOH< HF< H3O+< H2SO4Chapter 21. a) hydrocarbon with all single bonds, C3H8b) contains a carbon-carbon double bond, CH3CH=CH2c) contains a carbon-carbon triple bond, CH3C≡CHd) contains an OH group on a carbon, CH3CH2OHe) contains an oxygen between two carbons, CH3OCH3f) contains a carbonyl group between two carbons, CH3COCH3g) contains a carbonyl group with a hydrogen on one side, CH3CH2COHh) a cyclic hydrocarbon with alternating single and double bonds, benzenei) contains a carbonyl group with an OH on one side, CH3COOHj)contains a carbonyl group with an O-C on one side, CH3COOCH3k) contains a nitrogen bonded to one two or three carbons, CH3N-(H/R)2l) contains a carbonyl group with a nitrogen on one side, CH3CON-(H/R)2m) contains the carbon nitrogen triple bond, CH3C≡N2. a) sp3, 109˚ b)sp3, no angle because its only bonded to one atomc) C=C has sp2, 120˚ and nitrile has sp (C-N), 180˚d) all have sp3, 109˚ e) sp3 on both, 109˚ f) sp3 at OH and CH3, 109˚ sp2 at C and O, 120˚g) sp3 at CH3, 109˚ and sp2 at CH and NH, 120˚ h) sp3, 109˚ i) sp2, 120˚3. a) can hydrogen bond with self and water, moderately solubleb) can hydrogen bond with water, insolublec) can hydrogen bond with self and water, solubled) can hydrogen bond with water, insolublee) cannot hydrogen bond, insolublef) cannot hydrogen bond, insolubleg) can hydrogen bond with water, solubleh) can hydrogen bond with self and water,solublei) can hydrogen bond with water, soluble4. a) CH3CH(OH)CH3 b) CH3CH2CH2CH2CH3 c) CH3CH2CH2CH2CH3d) CH3CH2CH2CH2CH2Cl5. a) aromatic, 2 amides, thioether, and carboxylic acidb) 2 alcohols attached to an aromatic and an aminec) ether and alcohol attached to aromatic, amide, and alkened) alcohol and 2 aryl iodide attached to aromatic, ether and 2 aryl iodide attached to aromatic, amine carboxylic acide) ketone, alkene, alcoholChapter 31. a) b)c) d) e) f)g) h) i) j)k) l)2. HO-CH3 HO-CH2CH3 HO-CH2CH2CH3 HO-CH2CH2CH2CH3HO-CH2CH2CH2CH2CH3 HO-CH2CH2CH2CH2CH2CH33. a) 3-methylhexane b) 3-ethyl-2-methylhexane c) 2-chloro-3-methylhexaned) 2,2-dimehylbutane e) sec-butylcyclohexane or