mit-o1m4-ans

mit-o1m4-ans - 5.12 Prof. B. lmperiali Practice Exam #3...

Info iconThis preview shows pages 1–8. Sign up to view the full content.

View Full Document Right Arrow Icon
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 2
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 4
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 6
Background image of page 7

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 8
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: 5.12 Prof. B. lmperiali Practice Exam #3 Exam will be held Monday April 14th at noon. Notes and calculators will not be allowed in the exam but you will be provided with a periodic table and you may bring use molecular models to use. The exam will cover material from 3/12-4/11. The practice exam key will be posted as a separate file so that you can print up the exam and take it as a “real practice” before you check out the answers. Page 2 Short questions (1-9 3 points each and 10-12 4 points) 1. Estimate the pKa of the proton indicated. _______=—___._.H C] A. 50 B. 35 D. 5 2. Estimate the pKa of the proton indicated. OH <3 A. 30 c. 5 D. 1 3. Identify the major product of the reaction shown. H H Br :5.” H” $.— _ Brz —— ,.. “ ‘. ~‘ ’ H Hm ‘ H (in the dark) Br Br Br Br w A. B. \ c. M \f . ‘ 3F. 6: H ® 4. Identify the major product of the reaction shown. KO(CH3)3 Br ——-—> Page 3 Short questions Name __ 5. Which of the following terms is the best description of the alkene shown below. A. Cis Alkene B. Trans Alkene C. 2 Alkene 2‘: Alkene Momma $ 7. Which of the following compounds are formed when ethene is bubbled into an aqueous solution of bromine and sodium chloride? “3% {H30 { #31!qu I. BrCHchzBr l. CICH2CHzBr I. BrCHZCHZOH A. I and II 3- land I" C. II and III D. I II and Ill 8. Which of the following reagents effectively cleaves carbon-carbon double bonds? A. Bra and light B. meta-chloroperoxybenzoic acid c. 0304 follwed by H202 @3 followed by (CH3)2S Page 4 Short questions Name __ 9. Ozonolysis of an unknown compound gave CH2=O, CH3CHO and CH3COCHO. What are possible structures for the unknown compound? mtg; cg {:ch Q i 3 fit it) sit ammo 2' i 3 cflgtflm caiofli‘; L W "_ >j/= lll.//:<: IVA A. i and II 63nd IV C. II and Ill D. II and IV 10. Which of the following reactions does NOT occur as shown “A. CH3C_=_C'Na+ + CH3C02H —---> CH3C02'Na” + CH3CECH we. CH3CEC'Na” + CH30H —> CH30'Na+ + CH3CECH «o. CchECH + NaNH2 “4" “"3 + CHSCEC'NE” @CH3CECH + NaOH -—> H20 + CH3CEc'Na+ 11. Compound J undergoes a rearrangement to yield compounds K and L. Based on the potential energy diagram below which of the following statements is true? A. K is formed faster and is more stable Potential than L= energy J B. K is formed faster and is less stable than L C. L is formed faster and is less stable K Reaction coordinate Page 5 Short questions Name 12. Label the following pairs of molecules as E (enantiomers), D (diastereomers), or S (same molecule). Br 3 % gun a; 9‘ nlliUJ ..‘ 7“; Br Br Br 1“ £1 5H OH Br Br 7 % Br r E fig Olllln I ;3‘h 03 U3 Page 6 Long questions (Points as shown) Name 13. (16 points) For the following compounds, indicate whether they will react under 3N1 conditions (EtOH, A), 8N2 conditions (Kl/acetone), both, or neither. indicate the products and by which mechanism they are produced. H30 CH3 3N1 H3CXOTf “m9 % {I Efi'Qi‘i "Hia- /‘ ;o€'i’ T6 W m “A W G WWW” L H CO CI T Haw“ SN 2"” HSC wOMs M “f E OCH3 “Kg” 5M% 0 fiww Na “Mics gm? :3 fect& {of no. Page 7 Long questions (Points as shown) Name 14. (20 points) Design syntheses of compounds I and II (10 points each). The pool of carbon-containing starting materials that you can use are shown in the square brackets. You may use any other common reagents. l Lamé is! .5 om‘v Note: a clear retrosynthetic analysis will be useful for figuring these problems out. Partial credit will be given for a retrosynthetic analysis even if the synthesis is incomplete. @kwgfi? @flkfii": . Sfiul’ffifiis: H~s%c-M@ “9 Qfimw memifg j? {Tin @“w’l‘ x “M w r; Page 8 Long questions (Points as shown) Name 15. (24 points) Provide a detailed stepwise mechanism to account for the following transformations. 8 points each. 3N1 conditions ...
View Full Document

This note was uploaded on 02/23/2010 for the course CHEM 202 taught by Professor Smith during the Spring '10 term at Duke.

Page1 / 8

mit-o1m4-ans - 5.12 Prof. B. lmperiali Practice Exam #3...

This preview shows document pages 1 - 8. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online