A key - fictng Question 1(7 marks Anwg 4 my W WK a Circle...

Info icon This preview shows pages 1–5. Sign up to view the full content.

View Full Document Right Arrow Icon
Image of page 1

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

View Full Document Right Arrow Icon
Image of page 2
Image of page 3

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

View Full Document Right Arrow Icon
Image of page 4
Image of page 5
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: fictng Question 1 (7 marks) Anwg 4» my. W WK a) Circle the species that are aromatic. b) Label the following reactions as either REDUCTION, OXIDATION or NEITHER by printing the appropriate word above each reaction arrow. ammo) 0“ UEWH5K 0 ii) A )k —> H2C CH3 H3C CH3 / \ UEFMEL o o o >< —> + HOCHZCHZOH CH3 CH3 CH3 CH3 Question 2 (15 marks) Predict the major organic product(s) of the following reactions. Show stereochemistry at all chiral carbons and circle the term that describes the stereochemical relationship between the product(s). You do not need to include by-products of the reactions. Use the template(s) where given. 0 G CH3CH20H /\ /\K H a) CI _, i/ I 06 ZLH3 \\ enantiomers diastereomers @ structural isomers 1. 0 MgCl OH OH b) i j \w\.\ H /_\\ l I ~ H30 H —> < all?) \/ 2. H+ workup enantiomers diastereomers one product structural isomers CH CH 01' 1.H2,Lindlar‘s cat. H30 3 W H30 3 ll b so _ Br2 r1 0) H3C—C=C—CH3 L— Cllg. /°”% er. “ “a ll’ _, wuc / \u E V? “3 ll 5/ @ diastereomerssf ll one product structural isomers all 0 1. NaBH4 \A “(A d) COOH 2-“ Workup “age/W4 coon ’\ flWl’l \ A enantiomers diastereomers one product structural isomers 0 ll 0 CH 0 COOH e) meow exceSSCHsoH’W 3 \/\ 3 _, OH3O/\ enantiomers diastereomers one product structural isomers Question 3 (6 marks) a) The C-O bond in the compound on the right is much longer than the C-0 bond in the compound on the left. Explain this difference with a few sentences and by drawing some resonance forms. p. 1M6 resonana, st [HMS (womma {s 0L madar canlvbdl’bf, Since awwa (b w W35 gramme. mogul/natal \f MW‘W Col/dY‘llDW‘r, ofmr "s N 50 banal orolu "is “11 Single bands mt, Wan ’Mn don/Ho \omolxz- b) Why is base-promoted ester hydrolysis possible but base-promoted esterification is not? 0 0 Possible: NaOH + Na+ + ROH H20 R OR R o- 0 o N t ' | : 0 pOSSlbe i Na—’OR i + Na+ + H20 R OH ROH R 0R 0 /\0“ Jr 0K“ ’2 /“\o- +H0K M «Mel-Mm czaclxon 0% <3», WWw acid and whom-dz WM Occur Erwin/(Agar cud NOR/Wa/‘l'b can W9 [W M'f as an eltol‘: 095% an iv. 09% reaolxm. Question 4 (10 marks) a) Provide a synthesis of the compound on the right starting with the one on the left. This will require at least two synthetic steps. Show each step, providing the reagents that are needed and the intermediate(s) formed. You DO NOT need to show a detailed mechanism or stereochemistry. OH O_\ x \Z\ o?“ Vac ON} ’7 o( 30“” \/ ’3’ \40 b) In the boxes, write the reagent(s) required to carry out this multi-step synthetic transformation. Be sure to indicate if more than one equivalent is needed for any step. You DO NOT need to show a detailed mechanism or stereochemistry. BrHZC 0 CH3 OCH3 Question 5 (6 marks) Write the step-by-step mechanism for the following transformation. Show all electron movement arrows, relevant lone pairs of electrons, and reaction intermediates. All the reagents you need are given, DO NOT add additional reagents. \‘l O“ l H— H to COOW O \9/ / / —- ,> N CooH hag \l 17 < (4 g J Y on W GHQ 3 OH OH ’5 ...
View Full Document

{[ snackBarMessage ]}

What students are saying

  • Left Quote Icon

    As a current student on this bumpy collegiate pathway, I stumbled upon Course Hero, where I can find study resources for nearly all my courses, get online help from tutors 24/7, and even share my old projects, papers, and lecture notes with other students.

    Student Picture

    Kiran Temple University Fox School of Business ‘17, Course Hero Intern

  • Left Quote Icon

    I cannot even describe how much Course Hero helped me this summer. It’s truly become something I can always rely on and help me. In the end, I was not only able to survive summer classes, but I was able to thrive thanks to Course Hero.

    Student Picture

    Dana University of Pennsylvania ‘17, Course Hero Intern

  • Left Quote Icon

    The ability to access any university’s resources through Course Hero proved invaluable in my case. I was behind on Tulane coursework and actually used UCLA’s materials to help me move forward and get everything together on time.

    Student Picture

    Jill Tulane University ‘16, Course Hero Intern