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

Info iconThis preview shows pages 1–5. 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
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

This note was uploaded on 10/24/2011 for the course CHEMISTRY chem taught by Professor David during the Spring '11 term at UBC.

Page1 / 5

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

This preview shows document pages 1 - 5. Sign up to view the full document.

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