Chemistry XI Unit 9 Questions: 40 Time Limit: 40 minutes Passing Score: 60% Start Quiz Chemistry XI Unit 9 Question 1 of 40 Haloalkanes contain: halogen atoms bonded to C halogen atoms bonded to H halogen atoms in solution halogen as counterion Haloarenes contain: halogen bonded to aromatic carbon halogen bonded to aliphatic carbon halogen not bonded to C halogen with O Nucleophilic substitution in haloalkane: replaces halogen with nucleophile replaces H with nucleophile breaks C-C bond forms C=C bond SN1 mechanism: single-step process two-step process involves carbocation proceeds from back side SN2 mechanism: single-step process via carbocation direct substitution via back-side attack multi-step process no intermediate Rate law for SN1 is: first-order second-order third-order zero-order Rate law for SN2 is: first-order second-order third-order zero-order Stereochemistry of SN1: racemization inversion of configuration retention of configuration no change Stereochemistry of SN2: racemization inversion of configuration retention of configuration pyramidal SN2 is favored by: polar aprotic solvents polar protic solvents high temperature low concentration SN1 is favored by: polar protic solvents polar aprotic solvents non-polar solvents aqueous solvents Primary haloalkane undergoes: mainly SN1 mainly SN2 both equally no substitution Secondary haloalkane undergoes: only SN1 only SN2 mixture of SN1 and SN2 no reaction Tertiary haloalkane undergoes: mainly SN1 mainly SN2 both equally SN2 only Elimination reaction produces: alkene alkane alkyne ether E1 mechanism: single step two-step; formation of carbocation back-side attack syn process E2 mechanism: single step; bimolecular two steps involves carbocation sequential bond breaking Zaitsev's Rule in elimination: more substituted alkene forms less substituted alkene forms terminal alkene forms random alkene forms Hofmann elimination produces: more substituted alkene less substituted alkene (Hofmann product) only one product saturated compound Preparation of haloalkanes from alcohols: direct halogenation replacement by halide oxidation condensation Preparation of haloalkanes from alkenes: hydrogenation addition of HX substitution elimination In polar aprotic solvent, nucleophilicity order: I⁻ > Br⁻ > Cl⁻ > F⁻ F⁻ > Cl⁻ > Br⁻ > I⁻ all equal depends on temperature In polar protic solvent, nucleophilicity order: F⁻ > Cl⁻ > Br⁻ > I⁻ I⁻ > Br⁻ > Cl⁻ > F⁻ all same based on charge Base strength and nucleophilicity: always same independent generally parallel in aprotic solvents always opposite Grignard reagent is: RMgX R-X R-OH R-Cl Coupling reaction of Grignard: C-C bond formation C-H bond formation C-O bond formation C-halogen formation FILLBLANK:Rate of SN1 depends only on _____ RX concentration Nucleophile concentration Both RX and nucleophile Solvent only FILLBLANK:_____ is organometallic nucleophile RMgX. Grignard reagent Carbanion Alkyne Organolithium TRUE/FALSE: Haloalkanes have halogen bonded to aromatic C. TRUE FALSE TRUE/FALSE: SN1 rate depends only on RX concentration. TRUE FALSE TRUE/FALSE: SN2 is faster in polar aprotic solvent. TRUE FALSE TRUE/FALSE: SN1 produces inversion of configuration. TRUE FALSE TRUE/FALSE: SN2 causes Walden inversion. TRUE FALSE TRUE/FALSE: Primary haloalkane favors SN1. TRUE FALSE TRUE/FALSE: Tertiary haloalkane favors SN2. TRUE FALSE TRUE/FALSE: E1 and E2 both produce alkenes. TRUE FALSE TRUE/FALSE: Zaitsev product is less substituted alkene. TRUE FALSE TRUE/FALSE: Bulky base favors Hofmann product. TRUE FALSE TRUE/FALSE: HX addition to alcohol gives haloalkane. TRUE FALSE TRUE/FALSE: Grignard reagents are strong bases and nucleophiles. TRUE FALSE Previous Next Submit Quiz Want to save your progress? Create an account or log in to track your quiz scores! Register/Login