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TULANE / Chemistry / CHEM 2410 / What is syn-dihydroxylation?

What is syn-dihydroxylation?

What is syn-dihydroxylation?

Description

School: Tulane University
Department: Chemistry
Course: Organic Chemistry 1
Professor: Carol zhang
Term: Fall 2015
Tags:
Cost: 25
Name: FINAL EXAM STUDY GUIDE ORGANIC CHEMISTRY
Description: This study guide includes book notes and lecture notes, and little tricks I learned from the problems. Hope it helps!!
Uploaded: 12/08/2015
7 Pages 49 Views 3 Unlocks
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CHAPTER 6Don't forget about the age old question of What are the major organs in the cardiovascular system?

If you want to learn more check out What is the difference between recall and recognition?

  • Δ H = amount of energy needed to homolytically break bonds

  • To identify is Δ H is positive (+) or negative (-):
  • Broken = Positive (+), formed = Negative (-) ⇒ add all bonds together
  • Δ H o= ∑ D bond breaking (+) + ∑ D bond formation (-)
  • Entropy: disorder (S)
  • S TOT= S SYSTEM + S SURROUNDINGS 
  • substitution reactions create no change in energy
  • Positive (+) = spontaneous (favored)
  • To increase S:
  • 1. More molecules
  • 2. More freedom of motion (cyclic ⇒ noncyclic)
  • 3. Mover possible states
  • System achieves lower energy by giving energy to surroundings

  • Δ G o = Δ H o - T (Δ S o)

  • Positive (+) = endergonic (reactants more stable)
  • Negative (-) = exergonic (products > stable ⇒ spontaneous)

  • Equilibria:
  • → Δ G = -R(T)ln Keq
  • K eq > 1, Δ G o is negative (-) [products favored]
  • K eq < 1, Δ G o is positive (+) [products favored]

If you want to learn more check out It is when you have different outcomes, the factor that was not in common was probably the cause, what is it?

  • Kinetics:

  • Factors:
  • 1. E A: lower = faster
  • 2. Temperature: higher = faster (doubles for every 10 o increase)
  • 3. Steric Considerations
  • 4. Solvent


Don't forget about the age old question of What is the type of knowledge represented by a fitness leader’s skill in motivating his clients to adhere to a disciplined exercise routine, and one that is very difficult for the leader to explain to others is called?

CHAPTER 5We also discuss several other topics like What is expected for the future with regards to warming temperatures?

  • Δ H
  • Number of possible stereoisomers = 2 n (number of chiral centers)
  • Enantiomers, stereoisomers, and meso isomers
  • Chirality: non- superimposable mirror images
  • Chiral center: atom (tetrahedral sp 3) with 4 different gps
  • Chiral vs. Achiral (2 ethyl groups)

  • Cahn-Ingold Prelog System:

  • 1. Assign priority:
  • highest= highest atomic number
  • If 2 same, look to atoms bonded (compare the highest priority)
  • If double or triple bonds, it counts as being bonded to 2 or 3 atoms.

  • 2. Determine if R or S configuration
  • 4th priority on a dashed line
  • R: 1 → 2 → 3 Clockwise
  • S: 1 → 2 → 3 C.C.W -Counter Clockwise
  • 4th priority on a wedge:
  • R: 1 → 2 → 3 C.C.W
  • S: 1 → 2 → 3 Clockwise
  • If on solid → rotate

If you want to learn more check out What are the four domains of spoken language?

  • Enantiomers
  • Mirror image, non- superimposable
  • Configuration reverses from R to S, or S to R
  • All subs have opposite configuration
  • Diastereomers
  • Not mirror images
  • 2+ chirality centers → if between2 compounds. It is the same configuration.
  •  same subs have opposite configuration

Most reactive

Least Reactive

        Aldehydes (can use Na BH 4), ketones (can use Na BH 4), esters (only LAH works)

  • To make diol: diketone reduction or dihydroxylation of alkene

Grignard (R- Mg- X)

  • To make Grignard:
  • If acts as nu- ⇒ attacks C = O

  • Reaction:
  • If acts as base ⇒ attacks H+ (destroys Grignard!)
  • Requires H 2 O or H 3 O to add H at the end
  • Creates racemic mix

  • If ester ⇒ resonance form makes or a leaving group

  • Less stable negative (-) protonated first with H+

Synthesis Strategies

  • Alkylation of terminal Alkynes

  • Sn 2 process (cannot be done with 3 o sub)
  • To add carbon: tx with Na NH 2 and then whatever substrate you need attached to I - ion
  • 1. Na NH 2
  • 2. _____ I
  • Ex.
  • H - ≡ - H --(1. Na NH 2)--(2. E+ I)→ E+ - ≡ - --(1. Na NH 2)--(2. Me I)→ E+ - ≡ - Me
  • Alkylation inverts configuration (because Sn2)

  • Alkynide ion can act as nucleophile or base (E2 reaction)

As nucleophile:

  • Only primary halides will act as a nucleophile

                

As base

  • Elimination predominates with 2 o and 3 o halides
  • If base, attacks B hydrogen to eliminate leaving group
  • If nucleophile, attaches to C and leaving group leaves

  • In synthesis problems,
  • If anti-addition of 2X, do both reactions syn or both anti
  • If syn-addition: do one anti and one syn

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