{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

322af02_final_blank

322af02_final_blank - CHEMISTRY 322aL/325aL FINAL EXAM...

Info iconThis preview shows pages 1–7. Sign up to view the full content.

View Full Document Right Arrow Icon
CHEMISTRY 322aL/325aL Please _________________ FINAL EXAM Print Last Name DECEMBER 12, 2002 _________________ First Name SSN ______________ TA's Name____________ Grader (1) (45) _____ ______ Lab Day & Time_________ (2) (20) _____ ______ (3) (20) _____ ______ (4) (15) _____ ______ (5) (30) _____ ______ (6) (15) _____ ______ (7) (20) _____ ______ (8) (10) ______ ______ (9) (25) ______ ______ (200) first letter of last name I will observe all the rules of Academic Integrity while taking this exam. _______________________________
Background image of page 1

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

View Full Document Right Arrow Icon
Chemistry 322aL/325aL -2- Name_____________ Final Exam (1) (45) Complete the chemical reactions below by providing the organic product or products (as requested) within each box. You do not need to show byproducts of the reactions or any mechanisms. Show or describe stereochemical details in the products wherever they are important. "Workup' means adding water and bringing the solution to neutral pH. CH 3 C CHCH 3 OH CH 3 conc. H 2 SO 4 heat C 6 H 12 Product decolorizes cold KMnO 4 . Product shows single resonance in 1 H NMR. CH 3 Br H CH 3 H + Na + - C N CH 3 SOCH 3 (DMSO) C 8 H 13 N H 2 Pd CH 3 CH 3 CH 3 CHCHCH 3 CH 3 Br + NaOEt ethanol Product decolorizes Br 2 /CCl 4 . Show major product only. (A) (B) (C) (D) (E) CH 3 + HBr no peroxides C 6 H 11 Br
Background image of page 2
Chemistry 322aL/325aL -3- Name_____________ Final Exam (1) Contd. (F) CH 3 CH 2 CH 2 C=C H H CH 2 CH 2 CH 3 (i) hot KMnO 4 , HO - /H 2 O (ii) workup, H 3 O + C 4 H 8 O 2 (G) C 6 H 5 C CCH 2 C 6 H 5 H 2 Pd/C (poisoned catalyst) Product decolorizes Br 2 /CCl 4 (H) (I) (i) Hg(OAc) 2 /THF, H 2 O (ii) NaBH 4 , NaOH CH 3 ir: strong bands 3200-3500 cm -1 (J) OH + SOCl 2 Product gives a ppt with alcoholic AgNO 3 (CH 3 ) 2 C CH 2 O NaOCH 3 CH 3 OH C 5 H 12 O 2
Background image of page 3

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

View Full Document Right Arrow Icon
Chemistry 322aL/325aL -4- Name_____________ Final Exam (1) Contd. (K) THF.BH 3 THF (L) CH 3 CHCH 2 CH 2 OH CH 3 (i) NaH (ii) CH 3 CH 2 CH 2 CH 2 Br C 9 H 20 O (M) C OH CH 3 CH 2 CH 2 CH 3 CH 2 CH 3 conc. HCl 25 o C single enantiomer Product is insoluble in cold conc. H 2 SO 4 and give a ppt with alcoholic AgNO 3 (N) C=C CH 3 CH 2 CH 3 H H + CO 3 H CO 2 - 2 Mg 2+ ethanol C 5 H 10 O (O) CH 3 CH 2 CH 2 CH 2 OH (i) H 2 SO 4 (ii) CH 2 =C(CH 3 ) 2 C 8 H 18 O CH 3 CHCH 2 CH=CH 2 CH 3 C 6 H 15 B
Background image of page 4
Chemistry 322aL/325aL -5- Name_____________ Final Exam ( 2) (20) Answer the questions below. (A) (10) All valence-level electrons are shown in the structures below. Provide any missing formal charges in these structures. Place the charges immediately next to the atom on which they reside. Not all of the structures have missing formal charges. CH 3 CCH 3 O = : H CH 3 CH 2 CHCH 3 . H-B-H H H C=N H H H H CH 3 CH 2 CCH 3 CH 3 CH 3 CH 2 N : : CH 3 (B) (10) Indicate on the line below each structure whether the structure is chiral or achiral . In each structure, identify all stereocenters with an asterisk (*). A stereocenter is defined according to the definition in lecture and in our text. CH 3 CH 2 CHCH 2 Cl CH 3 CH 3 CH=CClCOOH C 6 H 5 CH 2 CH(CH 3 ) 2 H H OH OH CH O = OH H CH 3
Background image of page 5

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

View Full Document Right Arrow Icon
Chemistry 322aL/325aL -6- Name_____________ Final Exam (3) (20) Answer the questions below. (A) (10) Identify the pairs of structures below as constitutional isomers, enantiomers, diastereomers, or same compound. Be careful to select the most precise defining term.
Background image of page 6
Image of page 7
This is the end of the preview. Sign up to access the rest of the document.

{[ snackBarMessage ]}