HW7_key - arrow pushing step. (Hint: it is easy to find...

Info iconThis preview shows pages 1–6. Sign up to view the full content.

View Full Document Right Arrow Icon
CH318N Spring 2008 Name: UTEID: Homework #7 Due: Thursday 04-03-08 1. Please, fill in the empty boxes with appropriate structures and conditions. This problem was posted with mistakes! Reaction of alkyne was posted as hydroboration. However the rest of problem was designed implying “Markovnikov” hydration of alkyne under H 2 O/H + /Hg 2+ conditions. Therefore the answer for actually posted problem is following and some reactions are not very preparative! 1. BBN 2. H 2 O 2 , OH - H 2 /Pd/C PCC, or MnO 2 and many others N 2 H 4 /KOH ethylenglycol 180 o C AlCl 3 Cl O CF 3 CO 3 H HO O 1. LDA 2. acetone 3. N2H 4 , KOH, 200 o C O O OH + mess + mess + a lot of mess Below there is a key to the problem that should have been posted.
Background image of page 1

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

View Full DocumentRight Arrow Icon
O N 2 H 4 /KOH ethylenglycol 180 o C AlCl 3 CF 3 CO 3 H O O (CH 3 ) 2 CHPPh 3 Cl BuLi 1. H 2 O, H + , Hg 2+ Cl O PCC, or MnO 2 and many others NaBH4 OH
Background image of page 2
2. Please, fill in the empty boxes with appropriate structures. H O HO PCC, CH2Cl 2 O O O H + cat. H O O O SH SH H O O S S ZnCl 2 BuLi CH 3 I O O S S HgCl 2 , HCl (6N) H 2 O O HO HCl (6N) H 2 O HO S S Ni Reney, H 2 HO
Background image of page 3

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

View Full DocumentRight Arrow Icon
3. Draw the mechanism of the formation of the acetone dimethyl acetal explicitly showing every
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
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: arrow pushing step. (Hint: it is easy to find similar mechanism in the book and copy it but make sure that you understand the whole idea!) 4. Draw the mechanism of the Wolff-Kishner reduction of any ketone explicitly showing every arrow pushing step. (Hint: it is easy to find mechanism in the book and copy it but make sure that you understand the whole idea!) 5. Tollenss test is characteristic reaction for the aldehydes. However there is one, very simple organic acid that does give you false positive result of the Tollenss test. Beside silver mirror formation one can see evolution of gas bubbles during the experiment. Please, draw the structure of the acid and explain why being truly acid (pH ~ 3.75) it behaves as aldehyde. (Hint: this acid is also secret weapon of some ants) Formic acid. O O H H...
View Full Document

This homework help was uploaded on 04/15/2008 for the course CH 318N taught by Professor Willson during the Spring '08 term at University of Texas at Austin.

Page1 / 6

HW7_key - arrow pushing step. (Hint: it is easy to find...

This preview shows document pages 1 - 6. Sign up to view the full document.

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